The Ringer’s 100 Best Jay-Z Songs, Ranked

In the opening verse to one of Jay-Z’s best songs—we’ll get to that in a bit—Hov hits pause on the stories of boosters hawking clothes and dealers dodging police vans and speaks like a true-blooded rap fan: “I’m from where n----s pull your card, and argue all day about / Who’s the best MCs, Biggie, Jay-Z, or Nas?” That taps into the reality for anyone who lives and breathes this music—that no matter how dirty the hustler, no matter how big the star, no matter how average the fan, people love debating hip-hop supremacy.

Years after that song—“Where I’m From,” the crown jewel of Jay’s second album, In My Lifetime, Vol. 1—Jay and Nas would go to war over the answer to the question he posed. We are not here right now to relitigate that battle, or any type of MC hierarchy. Rather, we have a different question we’ve argued all day about: What’s the best Jay-Z song? And what better day to settle that debate than today, one day before the 25th anniversary of Jay’s debut LP, Reasonable Doubt—the legacy of which we’ve explored throughout the network today, in both print and on No Skips With Jinx and Shea.

In an attempt to answer that question, The Ringer gathered a brain trust of staffers and extended fam, asking them to submit their top 20 Jay-Z songs, ranked to the best of their abilities. In all, nearly 30 people participated. For some, it was an impossible ask—by some counts, Jay has appeared on 119 singles throughout his three-decade career, and that’s before counting album cuts and loosies. For others, the answers were simple—even with all those songs, there’s a clear order to the best of Jay’s best. The results of that extremely scientific voting process are below, where you’ll find the top 100 Jay-Z songs, ranked. The list includes not only Jay singles and album cuts, but also features, unreleased songs, and even a few freestyles. Basically, anything he’s rapped on was eligible.

Before we get to the list, a few insights into it. First, the no. 1 song was the runaway choice once all ballots were cast; it appeared on nearly every individual ranking, often high up. Second, while Jay would later reach far greater commercial heights than he did with Reasonable Doubt, the album is his most-loved, at least according to The Ringer. Check out the chart below:

Eleven of RD’s 14 tracks appear on this list. (And four of those pop up in the top 20.) After that album comes a tie between The Blueprint and The Black Album, Jay’s two greatest post–Reasonable Doubt critical successes, both of which had nine songs rank in the top 100 (and three inside the top 20). The most interesting album in the ranking may be Vol. 2, which placed only seven songs on the full list, but had three land in the top 20. The album was Jay’s commercial breakthrough, so it makes sense that its highs would be so revered, but 23 years later, deep cuts like “Ride or Die” don’t seem to hold up, at least for our staff. (“It’s Like That,” however, was robbed.)

On the other end of the spectrum, we had little interest in post-retirement Jay-Z albums aside from Watch the Throne. 4:44, Jay’s 2017 infidelity mea culpa, fared decently well with three songs on the list, but the disastrous Kingdom Come had just one and the return-to-form American Gangster had two (though “Success,” “Pray,” and “Blue Magic” ought to request a recount). And yes, you read that correctly, 2013’s Magna Carta Holy Grail has zero songs on this ranking. It’s in the judgment of this writer that our esteemed voting body made the right call—though there’s a compelling argument for “Beach Is Better.” “Tom Ford” acolytes and Samsung employees feel free to email me at [REDACTED]@theringer.com.

Speaking of Jay’s most- and least-beloved periods, since we’re including loosies and features, let’s look at the man’s apexes—again, according to the list.

While 1996 still ranks highly, you’ll notice a spike in 2003, which included not only The Black Album, but The Blueprint 2.1, “Crazy in Love,” and his “Pump It Up” freestyle. As fate would have it, Jay’s status appeared to be at an all-time high. And as much as we make fun of him not really retiring with his supposed swan song, he did seem to consider it the perfect time to say goodbye, at least initially, as there are no songs from 2004 on this list. (Jay did, however, give us a handful to choose from that year with the release of the Linkin Park mashup album and his second R. Kelly collaboration. Again, shouts to the voting body for doing the right thing.)

While we’re here, this ranking is also a great opportunity to look at who Jay’s strongest collaborators have been. Here’s another chart, this one of the producers who appear most in this list.

Jay didn’t link with Kanye until 2000, but the pair quickly became inseparable. Perhaps Jay discovered his musical soulmate. Or perhaps Jay, ever the capitalist, saw that Ye was redefining the sound of hip-hop and wanted in. Either way, we’re thankful they found each other—Kanye has more than twice as many appearances here as our second-most-popular producer, Just Blaze. (Also, a quirk of this list: By virtue of his work alongside Kanye, Mike Dean’s name appears more than Swizz Beatz’ and Bink’s and nearly as many times as Timbaland’s, despite those three producers’ significant work toward building Jay’s legend.)

Lastly, before we get to the proceedings, let’s pour one out for the songs that didn’t make it. Here’s a short list of honorable mentions:

• “Snoopy Track”
• “Threat”
• “It’s Like That”
• “Crew Love”
• “Blue Magic”
• “Young G’s”
• “Hovi Baby”
• “Pray”
• “December 4th”
• “Meet the Parents”
• “Rap Game/Crack Game”
• “The Watcher 2”
• “Shiny Suit Theory”
• “Kingdom Come”
• “Show You How”
• “Come and Get Me”
• “Nymp”
• “Success”

Apologies to the bereaved. Take comfort knowing that these songs would’ve made the list before “Sunshine.” —Justin Sayles

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100. Big L and Jay-Z 89.9 FM Freestyle (1995)

Producer: Mufi (for Miilkbone’s “Keep It Real”)

Even as a youngster, Jay-Z was typically the brightest star in his orbit. He may have rapped like the Fu-Schnickens in the pre–Reasonable Doubt days, but he still stood out on tracks like Original Flavor’s “Can I Get Open.” When he landed a spot on Big Daddy Kane’s “Show & Prove” posse cut, he didn’t shrink from the moment, delivering arguably the most memorable performance on the track (aside from a characteristically delirious Ol’ Dirty Bastard). But there was one MC who Jay could never seem to get the best of when they met up: Big L, the Harlem punch line kingpin and Diggin’ in the Crates crew member who seemed destined for big things in the mid-’90s. Jay played second fiddle to L on the latter’s “Da Graveyard” in 1995. That would also be the case when the pair visited Stretch Armstrong and Bobbito Garcia’s legendary radio show that February for a freestyle cypher.

Over the beat to Miilkbone’s “Keep It Real,” Jay and L trade rhymes and stories for over seven minutes. Jay is impressive—his cadence on the few bars that start with “You say never you run” is particularly seductive—but his sparring partner is the star, alternately hilarious and horrifying, like a slasher flick cut with a laugh track. And he did it all with a technical precision and a polysyllabic rhyme style that inspired a generation of backpackers to grab their pens years before Big Pun or Eminem arrived.

In the years after this late-night session, Jay’s stock quickly rose. He released three well-received LPs—each bigger than the last—and, in 1998, finally broke through to the mainstream with “Hard Knock Life.” Big L, however, would never get the chance to prove he belonged on the same commercial stage as Jay—he was shot and killed nearly four years to the date of that Stretch and Bob show. Jay, who repurposed one of the more memorable Big L lines from the freestyle on “A Million and One Questions,” would later say that Roc-A-Fella Records was in the process of signing L and his crew at the time of his death. “I think he had the ability to write big records and big choruses,” he said. —Sayles

99. “Lost One,” Featuring Chrisette Michele (2006)

Producers: Dr. Dre, Mark Batson

Yes, Kingdom Come isn’t as acclaimed as other Hov albums, but “Lost One” is a record that deserves a spin here and there. Why? The piano beat. The Chrisette Michele vocals in the background. The way Jay opens up his heart about his nephew who tragically passed away. Sure, it’s not a club hit or the first song you play when you’re on the aux, but it’s still a vulnerable piece of music that merits respect. —Jomi Adeniran

98. “On to the Next One” (2009)

Producer: Swizz Beatz

After the Daft Punk–sampling “Touch It” turned into an unlikely street hit, Swizz pulls from another French electronic duo to give Jay this Blueprint 3 single, which has aged better than nearly everything else from that album. Lyrically, like on much on the album, Jay isn’t in classic form, but he doesn’t seem to care: “Hov’ on that new shit, n----s like ‘How come?’ / N----s want my old shit, buy my old albums,” he taunts at the top of the opening verse. —Sayles

97. “Girls, Girls, Girls,” Featuring Q-Tip, Slick Rick, and Biz Markie (2001)

Producer: Just Blaze

Wow, this hasn’t aged well! —Danny Heifetz

96. “Best of Me, Part 2,” Mýa Featuring Jay-Z (2000)

Producer: Trackmasters

With age and success, Jay settled into his signature hip-hop professionalism. He wears suits and makes sophisticated pronouncements about wealth and family. But Jay used to wear throwbacks and spit game on R&B records—“Best of Me,” “Girl’s Best Friend,” “Heartbreaker”—and this was inarguably his strongest suit. —Justin Charity

95. “Streets Is Talking,” Featuring Beanie Sigel (2000)

Producer: Just Blaze

Coming three years after Vol. 1 standout—and inspiration for Jay-Z’s first film—“Streets Is Watching,” “Streets Is Talking” replaces the paranoia and street philosophy of the original with braggadocio and threats delivered the way only he can. (“You wanna conversate with the writer of the Qur’an / Or Old Testament? Don’t test him then.”) By this point, Jay had conquered rap; competitors were simply an annoyance to swat away. “Streets Is Talking” does so dutifully—and then lets Beanie Sigel ride out on them a capella, as if Jay were a mafia don making his lieutenant dispose of the body. —Sayles

94. “I Can’t Get Wid Dat” (1994)

Producer: Clark Kent

“How many styles I gotta kick to prove I’m def?” a pre–Reasonable Doubt Jay-Z asks while swerving between the rapid-fire delivery of his early career and the suave braggadocio he’d settle into. —Julian Kimble

93. “D.O.A. (Death of Auto-Tune)” (2009)

Producer: No I.D.

This song stands out for its sheer audacity, which is saying something given that Jay-Z built a career from immaculate bragging. Not content with battling fellow MCs, Jay-Z used this track to attack an entire sound. Fittingly, he did so over one of the most original beats of his career, a juggernaut of squawking guitars and howling clarinets from No I.D. It was classic Jay-Z in that he knew it would attract a massive backlash, and did it anyway—indeed, the backlash is exactly why he did it. As with the fight he started with Nas, this was a losing attempt—Auto-Tune continued to flourish—but that didn’t matter. What mattered was that, following a few years of good-to-indifferent creative outings, Jay-Z was back at the front of the pack, as the genre’s boldest, brashest ambassador. —Musa Okwonga

92. “Is That Your Chick? (The Lost Verses),” Memphis Bleek Featuring Jay-Z, Missy Elliott, and Twista (2000)

Producer: Timbaland

As long as Jay’s alive, Bleek’s a millionaire. And as long as Jay was pumping out hits in the late ’90s and early 2000s, Bleek was bound to be gifted one or two. The original version of this track starred Jay alone, but after he contracted Missy and Twista to hop on the final version, the song then made its way to Bleek’s second album, The Understanding.

Bleek would never become the star Roc-A-Fella hoped—the single was the understudy’s final song to crack the Top 100—but that’s not for lack of effort on Jay’s part. As one of the first artists signed to the label, Bleek featured prominently on Reasonable Doubt, The Dynasty, and Vol. 2, where he landed a solo song over a DJ Premier beat. Jay also jumped on plenty of Bleek songs. (Shout-out to the remix to “My Mind Right,” a song that didn’t chart but found life as a Tunnel banger.) But none truly resonated on a grand scale; even now, in 2021, Bleek is still one hit away. Something tells us he’s all right, though. —Sayles

91. “Change Clothes” (2003)

Producer: The Neptunes

Before I realized the name Jay-Z was a stand-in for both an MC and a conglomerate, I could be found, more often than I’d now like to admit, absolutely jamming to “Change Clothes.” What a beautiful and inharmonious portrait: a grown man scolding the clouds for wearing XXL throwbacks while a child vibes to the tune of his complaints. Blame it on those fuzzy keys or that zesty drum loop, quintessential Neptunes imports, but from the moment Hov sirened “the bounce is back,” it became a chore for anyone, let alone a Roc-obsessed elementary student, to not be hooked. And, by the way, “Change Clothes” isn’t a bad song. Jay’s not exactly in his pocket but he’s also not exactly out of it. He has that Star Wars reference in the first verse (“Let I breathe / Jedi Knight”), and that thing is still crafty as hell—to this day. He also has that pull-your-pants-up line (“Throw on a suit, get it tapered up”) at the end of his final verse, and that thing is still corny as hell. It’s hard not to let Hov slide. The track is just too damn catchy. Sometimes, in his line of work, that’s more than enough. —Lex Pryor

90. “22 Two’s” (1996)

Producer: Ski Beatz

Of course I’m supposed to focus on the first verse of this song where Jay-Z weaves in the combination of too, two, and to 22 times to power the concept behind the song. It’s impressive, sure. But what always felt interesting to me is the song’s sound design, creating the illusion that this song was recorded during some sort of live performance. And what I find even more interesting than that is the fictional host overreacting to the smell of weed in the club, and stating that as the reason our people can’t have nice things. The “shut the fuck up” from the crowd gets me every time. —Jonathan Kermah

89. “It’s Murda,” Ja Rule Featuring Jay-Z and DMX (1999)

Producers: Irv Gotti, Tyrone Fyffe

When Mic Geronimo dropped “Time to Build” in 1995, rap fans had no idea they were looking at the future of the genre. The track featured three relatively unknown MCs: Ja Rule, DMX, and Jay-Z. And while Mic Geronimo wouldn’t ever blow up, his guests would go on to dominate the charts in the late ’90s and early 2000s. The three of them even had a group planned: Murder Inc., a mob-indebted name that Ja and Irv Gotti would later use for their greatest successes.

Members of the trio would often guest on each other’s tracks, but they all appeared together only three times after the Mic Geronimo song: on the deep cut “If It’s On, It’s On” later in 1995, the Streets Is Watching soundtrack cut “Murdergram” in 1998, and “It’s Murda,” from Ja Rule’s debut LP in 1999. “It’s Murda” gets the nod here for DMX’s opening verse (“They got my back against the building, I’m the villain that’s creeping around corners / Like, ‘Shorty, if you see them n----s creeping around, warn us’”) and Jay’s casual, quick-witted threats (“Slumped, Kennedy-style with your memory out”), but Ja also floats here. While the Commission remains the ultimate Jay-Z what-if, the fantasy of a full-length album from Murder Inc. remains an intriguing thought experiment for rap nerds of a certain age. —Sayles

88. “Free Mason,” Rick Ross Featuring Jay-Z (2010)

Producer: The Inkredibles

By 2010, Jay-Z had had enough of the whispers. What’s a man to do when his riches are too vast and his wife is too gorgeous, and ne’er-do-wells calling for your demise are around every corner? If you’re Hov, you create a strawman masquerading as a very good Rick Ross song to wholeheartedly deny your involvement in an Illuminati-like secret society that’s responsible for your overwhelming success.

“Free Mason” is a letter to Jay’s “enemies” at a time when they’d all been vanquished. Within the first four bars, Jay alleges that an unnamed antagonist is wishing the devil on him and proclaims that the entire globe is praying for his downfall, despite white people playing the hell out of “Empire State of Mind” only one year prior. It’s the type of goofy mythmaking that marks much of Jay’s latter-era work. Beside peak-era Ross and backed by the Inkredibles’ grandiose beat, there’s a sense that the middle-aged rapper is rejuvenated. Hearing Jay rap with the world against him will forever be a treasure, whether it was funded by a fraternal organization from the Middle Ages or not. —Charles Holmes

87. “The City Is Mine,” Featuring Blackstreet (1997)

Producer: Teddy Riley

The second single from Jay’s weirdest album, released into the power vacuum that emerged among New York rappers after the death of the Notorious B.I.G. —Charity

86. “No Church in the Wild,” Kanye West and Jay-Z Featuring Frank Ocean and The-Dream (2011)

Producer: 88-Keys, Kanye West, Mike Dean

The opening track on the enormously anticipated (or, as my colleague Rob Harvilla put it at the time, the “long-threatened”) Jay-Z–Kanye West collaboration album Watch the Throne was the last one to be recorded. (“You got any beats on you?” is apparently what West asked the artist 88-Keys in June 2011 when the latter so happened to drop in to say hello. 88-Keys pulled up his SoundCloud; a modern-day elevator pitch.) Recursive and insistent, with a Jay-Z verse that includes references to Pious, Socrates, and Plato, the song sounds like a moody friend being held back from a fight in a parking lot, or like blood pumping through veins. Featuring contributions from The-Dream and Frank Ocean, the song is a fitting introduction to a bombastic, audacious album. —Katie Baker

85. “Excuse Me Miss,” Featuring Pharrell (2002) + “La-La-La (Excuse Me Miss Again)” (2003)

Producer: The Neptunes

“You can’t roll a blunt to this one; you gotta light a J … You can’t even drink Cristal to this one; you gotta drink Cristal.”

Remember when Jay was funny?

Carried by a typically futuristic-sounding Neptunes beat and a typically smooth Pharrell hook, “Excuse Me Miss” finds Jay Z spitting game, though with none of the desperation that drenched some of his earlier efforts. He’s comfortable, fully entrenched in a VIP section, puffing on a cigar, sipping Cristal, and eyeing one girl rather than 40. The wordplay is on max and the way Jay plays with how consonants sound is even more impressive. It’s love. It’s luxury. It’s, as Jay puts it, “for the grown and sexy.” —Andrew Gruttadaro

84. “Go Crazy (Remix),” Young Jeezy Featuring Jay-Z (2005)

Producer: Don Cannon

While not the first time Jay would jump on the remix to a bubbling Southern rap hit—that would be his lackluster turn on Juvenile’s “Ha” in 1998—“Go Crazy” stands as a capital-M Moment in hip-hop history. The track began life as a T.I. freestyle on the Atlanta legend’s Gangsta Grillz tape Down With the King. But the Don Cannon beat would make its way crosstown to the Snowman, who originally recorded a full song to it for his debut album on Def Jam, 2005’s Let’s Get It: Thug Motivation 101. Shortly afterward, an extended version featuring then–Def Jam president (and a then-retired) Jay-Z plus Terror Squad honcho Fat Joe would leak online, and an official remix would come out sans Don Cartagena (reportedly because of issues between Jay and Fat Joe). Jay’s verse would become synonymous with the song—so much so that the remix replaced the original on later pressings of Thug Motivation 101. “Go Crazy” isn’t a major piece of the Jay-Z story—it was a hit in large part thanks to Jeezy’s infectious flow and Cannon’s masterful chopping of an Impressions sample—but praise is still due to the Mariano of the Marriott, who knew how to rack up a save in a relief appearance. —Sayles

Photo by Kevin Mazur/WireImage

83. “Gotta Have It,” Jay-Z and Kanye West (2011)

Producers: The Neptunes, Kanye West

An infectious little ode to Black wealth and the musical empire that Jay-Z and Kanye built together. Dated most by references to Dwyane Wade and the once-viral planking meme. —Alyssa Bereznak

82.“A Week Ago,” Featuring Too Short (1998)

Producer: J-Runnah

Jay-Z has taken a lot from his late friend Biggie Smalls, but perhaps Christopher Wallace’s biggest influence on Hovito’s career has been his storytelling. In “A Week Ago,” Jay tells a tale of how his partner in crime snitched on him—how they were brothers a week ago, closer than brothers even. Again, it shows Jay as the smarter one and the ultimate victor. But this comes with an extra layer, about how snitching on your own messes up any opportunity for Black folks to get out of their circumstances, even if it’s through illegal means. Here’s Too Short’s explanation:

We was one step away from takin’ this crack money
And recyclin’ it through the ghettos
And buildin’ back up our own hoods
Now all you n----s start snitchin’ on each other
I got partners doin’ 15 to 20
Wouldn’t a been doin’ shit

However much you believe that to be true is irrelevant. Snitching, as the song suggests, messes up everyone’s plans. —Logan Murdock

81. “People Talkin’” (2001)

Producer: Ski Beatz

The cynical read is that Jay spent most of 2001 fiddling with the dials of his self-mythology: slowing his raps down to digestible mid-tempos, making sure The Blueprint scanned as serious in a way that would flatter establishment critics, then following it up with an MTV Unplugged session where he wore a Che Guevara shirt and was backed by the Roots. But there were some things he couldn’t let go. That MTV concert was taped just days before Nas released “Ether” and issued as an album the same day Stillmatic came out. Though it never mentions Nas by name, “People Talkin’,” the lone studio song tacked on to the end of the concert recording, is the sound of someone stewing. It’s easy to imagine Jay writing the passage that begins “Don’t you know when you’re defeated?” in a moment of triumph. But the perception that he’d been destroyed by a half-dead rival was calcifying quickly, and so this is left to sound, much more fittingly, like a plea made in vain. —Paul Thompson

80. “You, Me, Him and Her,” Featuring Beanie Sigel, Memphis Bleek, and Amil (2000)

Producer: Bink

Do you consider The Dynasty: Roc La Familia a solo album or a label compilation? The 2000 LP was originally slated as the latter before it was repackaged as a Jay project, perhaps to boost sales. But with crew songs like “1-900-Hustler,” “Stick 2 the Script,” and “The R.O.C.,” it was clear Jay-Z, Dame, and Biggs were pushing Bleek, Beans, Amil, and a newly signed Freeway as the next ones up. The best posse cut on the album, “You, Me, Him and Her,” shows off the full potential of Roc-A-Fella. Over a driving Bink beat, the second tier of the roster eats—even Amil, who delivers in a short, six-bar performance. The Dynasty may count as a solo Jay record, but the heart of it is these collaborations. —Sayles

79. “Some People Hate” (2002)

Producer: Kanye West

The Blueprint 2 isn’t bad; just long, sloppy, and lacking the egomaniacal clarity of the first album. Rather, The Blueprint 2 resembles a mixtape, and its best songs—“Some People Hate,” “Hovi Baby,” “Meet the Parents”—seem to be offering glimpses into his ideation. These songs aren’t hits but the glimpses are invaluable. —Charity

78. “Made in America,” Jay-Z and Kanye West Featuring Frank Ocean (2011)

Producers: Shama “Sak Pase” Joseph, Mike Dean

Jay and Kanye reflect on their extraordinary come-ups in America, acknowledging that they were made possible by the roads paved by Black activists, the determination of their own caretakers, and sweet baby Jesus. What the song lacks in lyrical flourish is made up for with Frank Ocean’s heavenly voice. —Bereznak

77. “Dope Man” (1999)

Producers: DJ Clue, Ken “Duro” Ifill, Darrell “Digga” Branch

Jay-Z’s love for sequels is far more evident in other corners of his discography, but “Dope Man” is the first of two songs within a calendar year on which Mr. Carter plays the defendant in a fictional court case (the second being “Guilty Until Proven Innocent” from The Dynasty, which dropped 10 months later). The precise storytelling, multiple characters, and dialogue makes “Dope Man” one of the standouts on Vol. 3. It’s also a fun little note that on a song built for Jay to flaunt his “ghetto spokesman” credentials, he admits to not being much of a fighter at the start of the third verse. As dope as any man might claim to be, a little self-awareness never hurts. —Tunde St. Matthew-Daniel

76. “Drunk in Love,” Beyoncé Featuring Jay-Z (2013)

Producers: Detail, the Order, Timbaland, Beyoncé, Jerome Harmon

Yes, OK, so as married-couple duets go, Jay’s verse here (which swerves from “beat the box up like Mike / In ’97 I’ll bite” to “Eat the cake Anna Mae”) is not the most, uh, romantic. But this all-universe highlight from Beyoncé’s self-titled 2013 masterpiece may be the precise moment when she eclipses Jay as the bigger and better and more eternally fascinating artist, and there is a supportive-husband grace in Jay just letting it happen: His line “your breasteses is my breakfast” is both (a) super gross and (b) a winking pass of the proverbial torch. Also, I did this song at karaoke once (both parts!), and it’s a top-5 worst moment of my entire life, though it left me with a greater appreciation for Jay’s ability to rap those words without instantly crumbling into dust. —Rob Harvilla

75. “The Ruler’s Back” (2001)

Producer: Bink

You get the most out of a person when they’re backed into a corner. After years of disses from Mobb Deep, Nas, and others, Jay used the opening track of his sixth album to lay claim to his throne as the genre’s best artist. It’s simultaneously a perfect intro and a flawless alley-oop to “Takeover.” —Murdock

74. “Pump It Up (Freestyle)” (2003)

Producer: Just Blaze (for Joe Budden’s “Pump It Up”)

Scattered across Joe Budden’s deep-internet catalog are innumerable grievances about his time on Def Jam’s shelf: being taken off a 112 single, 50 Cent and/or Jay leaving him home during the Rock the Mic tour, Lyor Cohen refusing to clear him for the “Get Low” remix. But the catalyst for his frustration with Jay seems to be the beat for “Pump It Up,” the Just Blaze–produced single that became a hit for Budden in 2003. It sounds like, at some point after the song began to take off, Budden asked if his then-labelmate would jump on a remix. Jay either quoted Budden an astronomical price or refused outright––a slight, maybe, but this was when Jay was finishing The Black Album and allegedly preparing to disappear for good. Only Jay couldn’t leave the beat alone. He freestyled over it for The S. Carter Collection, a mixtape he released in conjunction with his Reebok sneaker of the same name. It’s easy to read virtually any line here as a subliminal shot at Budden, but the real headline is the bone-chilling disrespect Jay shows to a handful of marginal NBA players. Maybe he threw Harold Miner some of the publishing. —Thompson

73. “Ain’t No N---a,” Featuring Foxy Brown (1996)

Producer: Big Jaz

Jay-Z’s name is on the record, but this is really Foxy Brown’s time to shine. Her verse on this track is special, and it’s even more incredible due to the fact she was only 16 when she wrote it. (Assuming she actually did write it.) From 2:10 on, you’re entrapped in her world as she matches Jay bar for bar in a truly impressive showing. —Adeniran

72. “It’s Hot (Some Like It Hot)” (1999)

Producer: Timbaland

Jay was feeling a bit chapped after the breakout success of Vol. 2. Why? Folks thought he went “pop/soft.” So he proceeded to spend an entire album unleashing rap fury on (mostly) unnamed nemeses—save for 50 Cent, whom he callously blasts on “It’s Hot” for saying Jay’s name on “How to Rob.” —Wosny Lambre

71. “Frontin’,” Pharrell Williams Featuring Jay-Z (2003)

Producer: The Neptunes

I guess it’s not a coincidence that I was assigned the blurb for “Frontin’” and “Excuse Me Miss.” Released just four months apart in 2003, the songs are of a pair, with Jay and Pharrell trading the spotlight for their respective tracks about flexing, faking it, and finally admitting to a more lasting kind of companionship. The elephant in the room with both songs, obviously, is Beyoncé Knowles, perhaps the only woman who could ever get Jay Z to admit that all that frontin’ comes from a place of insecurity. If “Excuse Me Miss” finds Jay beginning to come to terms with that profound point and the specter of a serious relationship, “Frontin’” finds him full on embracing those things:

I’m too old to be frontin’ what I’m feelin’
Denzelin’, actin’ like you ain’t appealin’ when you are
Stuntin’ like you ain’t my only girl when you are
(I was just frontin’) I’m ready to stop when you are

If that isn’t love, then I don’t know what is. —Gruttadaro

70. “Marcy Me” (2017)

Producer: No I.D.

After a series of largely uninspired solo projects with big-name producers or features propping up each track, 4:44 finds an older, wiser Shawn Carter putting out his best music in years. For his 13th studio album, Jay-Z limited the team-ups and stuck with No I.D. as his sole producer, all while creating a raw look at his long career and life in the spotlight. On “Marcy Me,” Jay-Z pays tribute to his native Marcy Houses. Over No I.D.’s smooth beat, Jay reminisces on his days growing up in the projects, and gives love to Brooklyn rap legends like Biggie and Big Daddy Kane. He reminds us that no matter how much times have changed, how much money he’s made or how many records he’s sold, Shawn Carter will never lose sight of where he’s from. —Daniel Chin

69. “The Joy,” Kanye West and Jay-Z (2011)

Producer: Pete Rock, Kanye West, Mike Dean, Jeff Bhasker

“The Joy” was first recorded during Kanye West’s sessions for My Beautiful Dark Twisted Fantasy, but it didn’t end up on the album. It’s technically not even on Watch the Throne, and is relegated to being a bonus track on a deluxe edition. Which is wild to me, because in my mind it’s the best song Kanye and Jay ever made together. The Curtis Mayfield–driven beat—which yes, deserves Hennessy, a bad bitch, and a bag of weed—is an ideal palette for both rappers to paint over, the slower tempo that allows them to be more reserved and contemplative on an album defined by excess. And while Kanye gets two verses to say some weird shit and crack jokes about girls named Bridget, the climax is saved for Jay-Z. “This is my mama’s shit,” he begins, kicking off a verse that reflects on his childhood—how much he’s thankful for it, and how much he’s thankful for the fact he survived it. It’s one of those rare moments in Jay’s discography when you feel genuinely close to him. Like you might even be able to know him. —Gruttadaro

68. “Dear Summer,” Memphis Bleek Featuring Jay-Z (2005)

Producer: Just Blaze

What an inimitable flex the act of floating is. “Like a butterfly,” was how Ali described his proclivity toward airlessness in the ring; and “it is I; be not afraid” were Christ’s words as he paced unto the waves in the Gospel of Mark; and so, likewise, on “Dear Summer,” Jay had to let us know that the reason he’d danced all up and down the track, with nary a footprint left behind, was because, “I do this in my slumber, summer.” He was supposed to be retired. The text arrived first via a freestyle with Hot 97’s Funk Master Flex in 2005 and was, about a year later, bolstered by perhaps the most beautiful bit of crooning soul Just Blaze has ever dusted off and retrofitted, an instrumental originally intended to appear on Memphis Bleek’s fourth album, 534. Upon first listen Hov just couldn’t help himself, and Bleek knew a miracle when he saw one. The track stayed on the album as a Jay solo. “Summer” in this case refers to the rap game, which he’d dominated for more than a decade—especially, like clockwork, during the warmer months. So you could say the song is less a letter to a season than a testimonial to a community or, even more, from one. Has the man ever really been better? Every stanza is dizzying and merciless and, not unrelatedly, downright perfect. The audacity to venture “I don’t talk shit, I just flip it Un ya,” before eventually bowing out, “Young n----s that blast for me, no religion.” Grotesque. Also, flawless. What a move. “You lucky,” Hov boasts, “I got a good groove.” —Pryor

67. “Jigga My N---a” (1999)

Producer: Swizz Beatz

Jay-Z typically reserves his best for his own albums, but this gem—which first appeared on Ruff Ryders Vol. 1—was a perfect opportunity: Talking cash shit on another clique’s project during his victory lap between Vol. 2 and Vol. 3. —Kimble

Photo by Kevin Mazur/Getty Images for Parkwood Entertainment

66. “03 Bonnie & Clyde,” Featuring Beyoncé (2002)

Producer: Kanye West

If you asked critics in 2003, they’d probably tell you “03 Bonnie & Clyde” was a highlight of Hova’s solid, if slightly commercial, seventh album. But if you asked me, a Napster-addicted middle schooler whose personal god was Total Request Live’s Carson Daly, it was the pinnacle of early-aughts pop culture. The song’s cinematic flamenco-guitar-seasoned beat—a Kanye West reprise of Tupac’s “Me and My Girlfriend”—made it a staple on many a burnt CD, and Jay-Z’s reference-rich flow was as rhythmic as it was instructional. (I distinctly remember googling “burberry bikini how much” and being very disappointed.) The song was Jay-Z and Beyoncé’s first collaboration, and both the mention of romantic titles and the sweltering music video stoked speculation of their involvement before the term “ship” ever made it into the mainstream vocabulary. As their power coupledom grows more mythic by the year, the song has become a founding text. They extended the outlaw metaphor on “Part II (On the Run),” which inspired a 2014 world tour complete with bandanna merch. Beyoncé later tipped her hat to that coveted Burberry swimwear by wearing the brand in a music video the couple shot for their 2018 victory lap Everything Is Love. “03 Bonnie & Clyde” is the rare example of a song whose importance as a cultural artifact far exceeds its musical attributes, it’s just a bonus that it remains a strong addition to a barbecue playlist. —Bereznak

65. “New Day,” Jay-Z and Kanye West (2011)

Producers: RZA, Kanye West, Mike Dean, Ken Lewis

“Sorry Junior, I already ruined ya / ‘Cause you ain’t even alive, paparazzi pursuin’ ya.” When Watch the Throne hit in August 2011, both Jay and Kanye were still childless, still planking on a million, still rapping too much about Andy Warhol. But this RZA production—certainly not the first flip of Nina Simone’s “Feeling Good,” but arguably the lushest—graced that cornball-hedonist album with a startling flash of melancholy and new-parent trepidation, wherein Jay’s ode to an unborn son manages to sound both relatable (“I just wanna take ya to a barber”) and imperial (he rhymes that with “bonding on charters”). With seven kids and a lifetime’s worth of familial tabloid chaos generated between the two rappers since, the gorgeous unease of “New Day” never gets old. —Harvilla

64. “Crazy in Love,” Beyoncé Featuring Jay-Z (2003)

Producers: Rich Harrison, Beyoncé

It’s your boy, Young! “I asked Jay to get on the song the night before I had to turn my album in,” recalled Beyoncé in 2011 to Billboard about “Crazy in Love,” the lead track (and lead single) on her debut (omg, were we ever so young?!) solo album Dangerously in Love. The resulting collaboration would become a forever-favorite of college marching bands across the nation and remains a key chapter in the origin story of one of the music industry’s most powerful couples. (Its release in May 2003 came on the heels of months of “03 Bonnie & Clyde” and matching-denim-fueled are-they-or-aren’t-they speculation; Jay-Z rapping “Young B and the R.O.C.” seemed as good a confirmation as any.) With its sampled horns shepherded by hungover producer Rich Harrison and Jay-Z’s then-timely references to Tony Soprano and Nick Van Exel in his verse, “Crazy in Love” wasn’t just the song of the summer—although it certainly was that—it was the sound of an era. —Baker

63. “Drug Dealers Anonymous,” Pusha T Featuring Jay-Z (2016)

Producer: DJ Dahi

Jay and Pusha T, two of the most prolific coke rappers in history, team up to brag about their exploits and end up rapping about the home renovations the drug trade has paid for. The question here isn’t who has the better verse but who has the better house: Jay with koi ponds and a marble foyer, or King Push with his all-glass quad-level design? Let no one ever say the game wasn’t good to these two. —Sayles

62. “What More Can I Say” (2003)

Producer: The Buchanans

This is just a demonstration of the art form. It starts in typically cinematic fashion with an extract from Gladiator, and then launches into an equally epic score, Jay’s flow rolling out over the beat like a red carpet. As a writer, I have always been fascinated by Jay-Z’s usage of words, given that he never wrote anything down. If you have never put words on a page, then you are liberated—you aren’t tied to having to fit them neatly within lines and margins, so they tumble everywhere. You can define the greatest MCs by their ability to use a seemingly infinite variety of flows, and by the time Jay-Z has finished this track, speaking a cappella after the instrumental has succumbed to him, you have lost count of the array of styles he has used. A master class. —Okwonga

61. “Brooklyn Go Hard,” Featuring Santigold (2008)

Producer: Kanye West

Following the success of “Stronger,” Kanye spent 2008 in his Hype Machine bag, turning vocal samples from blog hits into actual hits. First came “Swagga Like Us,” on which he sampled M.I.A. for himself, Jay, T.I., and Lil Wayne. Next came “Brooklyn Go Hard,” which flipped four words from a Santigold song into a canvas worthy of Jay’s contribution to the Notorious soundtrack. The latter gets the nod here for featuring one of the most dazzling flows of Jay’s post-retirement stretch. Hell, the Jackie Robinson wordplay by itself would’ve probably been enough to place it on this list. —Sayles

60. “Grammy Family” Freestyle (2006)

Producer: Kanye West, Jon Brion (for DJ Khaled’s “Grammy Family”)

If “Brooklyn Go Hard” features one of the most dazzling flows of Jay’s post-retirement career, then these verses he dropped during an October 2006 visit to Funk Flex’s radio show may be the apex. Over the course of nearly five minutes, Jay name-checks Malcolm, Martin, Julius Caesar, Biggie, Tupac, Kurt Cobain, Albert Pujols, and Phil Rizzuto’s Money Store ads. The album he was there to promote—his comeback dud Kingdom Come—may have bombed, but anyone questioning whether Hov fell off needed to look no further than this freestyle for an answer. (Also, massive shout-out to the person in the YouTube comments who took Jay’s Gordon Gekko boasts to heart: “This freestyle changed my life. Became a business major after hearing this and now I have my own company.”) —Sayles

59. “Reservoir Dogs,” Featuring The LOX, Beanie Sigel, and Sauce Money (1998)

Producers: Erick Sermon, Rockwilder, Darold “Pop” Trotter

Though the song belongs on Vol. 2, The LOX more or less own “Reservoir Dogs.” Jadakiss said, “Gangsters don’t die, they get chubby and move to Miami,” and while Jay drops some slick bars about the New Jersey Turnpike, he can’t top Kiss, Styles, and Sigel’s respective contributions. But we’re not ranking performances, we’re ranking songs, and “Reservoir Dogs” sits high in his discography on the strength of his once-and-future frenemies. —Charity

58. “I Love the Dough,” the Notorious B.I.G. Featuring Jay-Z and Angela Winbush (1997)

Producer: Easy Mo Bee

This joint feels rich—and not just in the opulent, luxurious subject matter Biggie and Jay portray over the five-minute track. It’s a moment when two of Brooklyn’s finest performers celebrate their riches together. The moment is so good, it seems fleeting—like we should enjoy it while we have them both on this earth. That alone is worth a replay. —Murdock

57. “Poppin Tags,” Featuring Big Boi, Twista, and Killer Mike (2002)

Producer: Kanye West

With a crew like this, there was never a chance in the world this song would be a miss. As expected, Kanye delivers on a perfect soul sample beat. Twista, Killer Mike, and Big Boi do their thing, also as expected. Sleepy Brown sounds as smooth as ever on the hook rapping about the luxuries that come with hustling. But what’s most impressive is Jay-Z’s ability to keep up with the other rapper’s electric flows while never compromising his coldness. —Kermah

56. “Murder to Excellence,” Jay-Z and Kanye West (2011)

Producers: Swizz Beatz, S1

My God. Possibly the most underrated song with which Jay-Z has ever been associated. Everything about it is astonishing. “I arrived on the day Fred Hampton died,” says Jay-Z, and the whole thing begins to ascend. Why this was not released with a video I do not know. It could have featured all of Jay-Z and Kanye’s illustrious friends, and it would have been an instant classic. This song was so powerful because it made me feel that these people have made all their money but are not detached from reality, they still understand, they still keenly feel the ravages of racism. And, crucially, they still care. It features some of the best lyrics from both MCs, including, in my view, Jay-Z’s cleverest line of all, and one of the best to emerge from hip-hop: “Domino, domino / Only spot a few blacks the higher I go.” It’s surprising to find a song as soulful at the center of an album called Watch the Throne, but I believe that it is the record’s emotional core. It’s a track as spiritually powerful as Kanye’s “Jesus Walks,” and I don’t say that lightly. —Okwonga

55. “Diamonds From Sierra Leone (Remix),” Kanye West Featuring Jay-Z (2005)

Producers: Kanye West, Jon Brion, Devo Springsteen

Highlighted by his “I’m a business, man!” declaration, Jay-Z’s feature on the “Diamonds” remix was peak Hov, floating over an explosive beat while laughing at detractors, boasting about his wealth, proclaiming protection for his own, and suggesting he can do the impossible with little-to-no effort. It’s definitely one of his most memorable features. —Kaelen Jones

54. “Encore” (2003)

Producer: Kanye West

“Encore” is good. But the “Numb/Encore” collab between Jay-Z and Linkin Park is great. Between the opening riff (Buhbuh-BUHHHH-buh) and then Jay-Z’s intro (“Thankyouthankyouthankyou, you’re far too kind!”) this song is a time capsule back to the days when people actually buried time capsules. —Heifetz

53. “Clique,” Kanye West, Jay-Z, and Big Sean (2012)

Producer: Hit-Boy

What a song. Coming off the highest of highs of Watch the Throne, Kanye and Hov delivered again in a big way. “Clique” appears on Kanye West’s 2012 compilation Cruel Summer. Full of posse cuts and incredible guest verses from Ghostface Killa and 2 Chainz, few bars hit harder than Jay-Z’s verse. I mean, do you remember the heat???

Turn that 62 to 125, 125 to a 250
250 to a half a million, ain’t nothin’ nobody can do with me

Not only did that line make a great vine, but nine years later, I can still think back to the first time I heard that song at my high school’s winter formal. Of course, Jay has had much bigger hits in his career considering he’s, y’know, JAY-DASH-Z, but “Clique” stands the test of time as a certified banger. —Adeniran

52. “Regrets” (1996)

Producer: Peter Panic

When people speak of Hov’s microphone mastery they’re generally speaking of either the mechanically precise flow or the preposterously dense lyrics. On “Regrets” it’s absolutely the latter—the “monster of the double entendre” at his apex. —Lambre

51. “From Marcy to Hollywood,” Featuring Memphis Bleek and Sauce Money (1998)

Producers: Ken “Duro” Ifill and DJ Clue

Throughout Jay’s career, Memphis Bleek became a punch line, and his earliest partners, such as Sauce Money and Jaz-O, were relegated to the margins of Jay’s origin story. But I love revisiting his one song with Original Flavor, and I love revisiting “From Marcy to Hollywood,” a song preserving the hustler’s old, coldest wisdom—“She loved that I was a thug, it turned her on / Soon as I got soft, it turnt her off”—before Jay would go on to spin the wisdom into mythology and clichés. —Charity

50. “In My Lifetime (Remix)” (1994)

Producer: Big Jaz

Credit Jaz-O, Jay-Z’s former mentor, for polishing the original “In My Lifetime” into this early standout in which illicit activity is the answer to a lingering existential question. The remix’s summery feel belies its sinister narrative, as Jay-Z recounts the tale of a hustler on the rise doomed by the same ambition that propels him. “I know the price, know the risk, know the wrongs and the rights / Still my blood flows ice, it’s just my life,” he announces just before the chorus. Take a ruthless pursuit of the “American Dream” and mix it with myopic feelings of invincibility—the end result is a tragic, but unsurprising outcome. As someone who escaped the crack era with his freedom, Jay-Z knows the threat of death or incarceration won’t scare young hustlers away from rolling the dice when they’re without opportunity or fucks to give. Even if they claim to understand what’s at stake, the thrill of fast money makes it worth the gamble. “In My Lifetime” is a familiar cautionary tale—ascent, recklessness, demise—but goddamn if Jay-Z doesn’t capture the awe of newfound success, however fleeting, perfectly. —Kimble

49. “Do It Again (Put Ya Hands Up)” (1999)

Producers: Rockwilder

Low-key one of Jay’s greatest club bangers. Over the best Rockwilder beat not crafted for a song named after him, Jay unspools a torrent of misogyny and crass materialism, alongside a nod to Big Daddy Kane. It’s a spell-binding verse that doesn’t often get discussed as one of Jay’s best. Perhaps it’s time that changed. (Also: Shouts to Amil, who delivers the most memorable verse of her abbreviated career and shows that disrespect to the opposite sex can be a two-way street in hip-hop.) —Sayles

48. “You Must Love Me” (1997)

Producer: Nashiem Myrick

It’s remarkable how Jay-Z, at one point, convinced the world he was infallible. He’s as image-conscious as they come, but seems aware that his moments of vulnerability have always yielded some of his best music. The In My Lifetime, Vol. 1 era, which was just before he unlocked the formula for his mega-success, produced what remains one of the rawest confessionals of his meticulously calculated career: “You Must Love Me.” Be it the mother he constantly disappointed, the brother he shot, or the ex who helped him move drugs, Jay-Z details how he did wrong by each of them over the steady churn of Nashiem Myrick’s solemn production. Each verse ends with him repeating the song’s title, still astonished he’s been forgiven for his transgressions. “You Must Love Me” is an apt conclusion to Vol. 1—before Jay-Z could rise to fame through the projection of a Teflon exterior, he had to exorcise the demons he’d harbored for years. —Kimble

47. “Money, Cash, Hoes,” Featuring DMX (1998)

Producer: Swizz Beatz

A “Kevin Durant vs. Giannis Game 7”–level showdown: two superstars with drastically different personas and styles, sharing the same big stage and delivering an instant classic. DMX came through with his signature ad-libs on the hook, Swizz Beatz laid an attention-grabbing beat, and Jay-Z, in his final bar, predicted his own future as a New York Times bestseller. To bite a line from No Skips With Jinx and Shea: “Damn, that’s hard as f**k!” Lastly, in addition to other great Jay and X collabs (including their legendary freestyle battle and that one brief Jay-Z cameo in the “What’s My Name?” video), this track is a welcome relic from the friendly, supporting rivalry these two greats shared while they were both on top of the game. —St. Matthew-Daniel

46. “Who You Wit II” (1997)

Producer: Ski Beatz

The track from Jay’s second album, In My Lifetime, Vol. 1, is a pretty good snapshot of who Jay was back in 1997—and a retrospective reminder of how he evolved. “Who You Wit II” combines a smoothed-out jazz beat (borrowed from Jeff Lorber Fusion’s early-’80s “Night Love”) with the big, braggy lines that came to define Hov. When he offers that he can and will “match wits with the best of y’all,” he’s not lying, and he backs it up over the course of his career. It’s impossible not to bob your head as he boasts about “frames with the French name,” “custom drop Bentleys” and partying “like Lil Pennies.” If that’s not perfectly of the era, what is? And yet like a lot of things from the ’90s, the song has more than a few cringey moments upon review. The beginning features an unsurprising overuse of the word “bitches” and deteriorates rapidly from there on the female front. The song is both good and dated. As with most matters related to Jay, several things are true here at once. —John Gonzalez

45. “Roc Boys (And the Winner Is) ...” (2007)

Producer: The Hitmen

The second single off of Hova’s conceptual American Gangster is a swaggy acceptance speech for no award in particular. Against exuberant trumpets, Jay-Z thanks the many people from his drug-dealing days who made his ascendence from the hood possible, including but not limited to: his connect, several makeshift containers for drugs and money, and corrupt cops. “Roc Boys” is both a return to Hova’s storytelling roots and a preview of the type of celebratory “Black superhero music” that he and Kanye would perfect on later albums. —Bereznak

44. “Renegade,” Featuring Eminem (2001)

Producer: Eminem, Luis Resto

I played this song in the car with my mom in the mid-aughts. She wanted me to turn it off (because Eminem). Right on cue, Eminem directly addressed parents listening to his music. “I’m debated, disputed, hated, and viewed in America as a motherfucking drug addict—like you didn’t experiment?!?!”

We listened to the rest of the song.

Eminem was the only feature on The Blueprint, which makes sense because Eminem was the only rapper in 2001 with Jay-Z’s flow and fame. Nas famously dissed Jay by saying that “Eminem murdered you on your own shit” in reference to this song. Even Jay-Z acknowledges that. So does my Mom. —Heifetz

43. “4:44” (2017)

Producer: No I.D.

For all of the bravado and vanity littered throughout Jay-Z’s discography, “4:44” not only signaled a deviation in Hov’s rap persona, it also presented his most transparent and vulnerable soul-baring to date. Fittingly backed by sampling of Hannah Williams and the Affirmations’s brilliant and soulful “Late Nights & Heartbreak,” Jay-Z apologizes to Beyoncé, who released Lemonade a year before, for his infidelity and other shortcomings as a partner in their relationship. He repeats “I apologize” seven times during “4:44,” more than in the rest of his entire catalog combined.

There are unfaithful partners in this world (with significantly lesser résumés) incapable of displaying the level of remorse Jay-Z expressed on “4:44,” making his humility a decent action. It doesn’t water down the severity of his misdeeds, but his direct ownership of the pain he caused—rather than reveling in the thrill of it, like his past persona might have seemingly done—unveiled a regretful version of the billionaire businessman that certainly felt moving and painfully human. —Jones

42. “Run This Town,” Featuring Kanye West and Rihanna (2009)

Producers: Kanye West, No I.D.

When The Blueprint 3 came out in 2009, it was Jay’s 11th studio album. He was 39 at the time. There was some question—not by me, perhaps by you—about how much he had left and whether he had already aged out of the game. Whether he was actually short on believers during that period was and remains immaterial; Jay has always taken aim at his doubters — real and perceived. And in “Run This Town” he made it pretty plain who was still in charge, lest any of us had forgotten or thought otherwise. The way Jay saw it then—and now, and always—is that you can call him Caesar while “the other side” might as well “throw they hand in cause they ain’t got no spades.” (As a spades player since I was a kid, I’ve always loved that line.) Putting Rihanna and Kanye on the track was just one more flex in his muscular music portfolio. —Gonzalez

41. “The Story of O.J.” (2017)

Producer: No I.D.

I had given up on Jay-Z. Not really, but really. Four years removed from Magna Carta Holy Grail, an album I assiduously tried (and failed) to enjoy, there wasn’t much reason to expect that Hov could reclaim his status as the centrifugal force of hip-hop. And “The Story of O.J.” didn’t exactly do that, but it redefined his exit plan. Jay still raps here and there, but 4:44 came to represent proof that one could age gracefully in rap while still recording relevant records. He did so by abandoning the disciplined, hyper-focused rhyme style that he had honed, refurbished, and renovated so many times over his three-decade recording career and instead replaced it with a kind of talking blues. It’s not Jay’s best song, but it is the one in which he feels most his age—46 at the time of recording—and humbled by a lifetime of success. For decades, Jay tried to show you what the world could give you if you hustled it right. “The Story of O.J.” is working together, not winning. What a concept. —Sean Fennessey

Photo by Lester Cohen/Getty Images

40. “Lucifer” (2003)

Producer: Kanye West

Old man Jay, like most elderly people, loves talking about religion. One of the clearest examples that Hov was getting up there in age by the time of his supposed “retirement” record was how much The Black Album circled ideas of birth, death, and the sins we leave behind in our wake.

Nowhere is this more exaggerated than on “Lucifer.” Over Kanye West’s chop of Max Romeo’s “Chase the Devil,” Jay throws himself in a Catholic confessional of his own making. He’s slightly apologetic before remembering that having a conscience is boring, while leaving your enemies on respirators for killing your best boy is not. It also doesn’t help that Jay allegedly made a devil’s bargain with Bump J and traded the amazing bar “I’m from the murder capital, where we murder for capital” for the far less iconic, “A n---a can’t tell me I ain’t livin / Birds on the table now that’s a Thanksgiving.” —Holmes

39. “What We Do,” Freeway Featuring Jay-Z and Beanie Siegel (2002)

Producer: Just Blaze

Make no mistake: This ode to desperate measures is Freeway’s shining moment. Jay-Z’s words of encouragement (“Keep goin’”) were supposed to be the extent of his contribution, but he reunited three-fourths of the crew responsible for “1-900-Hustler” by giving the Philly rapper a full verse for his debut single. There was no matching Freeway’s urgency, so Jay found a way to be effective in a complementary role, flashing his wit (“Gotta kill witnesses ’cause Free’s beard’s stickin’ out”) while spelling out the extremes hustlers resort to out of self-preservation. —Kimble

38. “Empire State of Mind,” Featuring Alicia Keys (2009)

Producer: Al Shux

“I feel like I have this record that’s going to be the anthem of New York,” is what Alicia Keys remembers Jay-Z telling her in a phone call requesting her involvement in the 2009 smash hit “Empire State of Mind”—and he was right. Originally written by two homesick New Yorkers, Angela Hunte and Janet Sewell-Ulepic, during a trip abroad, “Empire State of Mind” is a soaring, loving, ball-busting ode to a dirty and beautiful city. Based off a piano sample from the 1968 song “Love on a Two-Way Street” by the Moments and revamped with Jay-Z’s self-reverential, self-referential verses, the song channels performers from Billy Joel to Frank Sinatra to Biggie and shouts out entertainers ranging from Robert De Niro to Spike Lee. (There’s also the quite informative NBA-drugs-numerology triangle.) “Yellow cab, gypsy cab, dollar cab, holla back” is a fitting line for a song that feels like the best New York City cab ride you’ve ever taken, the kind where the windows are down and the lights stay green and the city scrolls endlessly around you. —Baker

37. “Politics As Usual” (1996)

Producer: Ski Beatz

Unlike a young Kanye on College Dropout’s “Last Call,” I tend to gravitate toward a more introspective Jay-Z. While the lyrical content of “Politics As Usual” leans mafioso and street business, the track’s effortless flow and sample-heavy sound has hints of the smooth soulfulness of later Kanye-produced Jay hits such as “Guess Who’s Back” and “This Can’t Be Life.” Also, while Reasonable Doubt was Jay’s entrance into rap’s ring of heavyweights, on “Politics As Usual,” Jay-Z—ironically and clairvoyantly—predicts Mike Tyson’s “major night off” vs. Evander Holyfield, which happened just months after the album dropped. —St. Matthew-Daniel

36. “Money Ain’t a Thang,” Jermaine Dupri Featuring Jay-Z (1998)

Producer: Jermaine Dupri

The way Jermaine Dupri tells the story, it all began in 1996, when a remix of Dru Hill’s “In My Bed” that he worked on with Da Brat caught the ear of Jay-Z. Everything snowballed from there: Jay-Z referenced that song on a mixtape; the two artists crossed paths a couple of years later at an iconic XXL photo shoot; and soon Dupri found himself driving to pick up Jay-Z at the airport, listening to the rising star’s 1996 album Reasonable Doubt for inspo and being struck by a line on “Can’t Knock the Hustle” (feat. Mary J. Blige!): “I’m deep in the South kicking up top game / Bouncing on the highway switching four lanes / Screaming through the sunroof, money ain’t a thang.” From that, a new song was born, featuring the “Weak at the Knees” beat; lines like “I’ve been spending hundreds since they had small faces,” and a flashy, lively music video featuring a future Real Housewife. Some songs have truly lush family trees. —Baker

35. “Allure” (2003)

Producer: The Neptunes

Jay-Z was skeptical when Pharrell laid out his vision for what became “Allure” in Fade to Black, but you can pinpoint the moment in the 2004 documentary when the music starts to come alive in his mind. Between every somber key, pained synth, and ominous gunblast, he sees the big picture: a weary man addicted to the rush of his lifestyle and resigned to his fate. Beyond exploring the inner thoughts of someone who’s compartmentalized for his own gain, Jay nods to the plight of every woman who risked her freedom in the name of love. “Allure” is as haunting as it is beautiful: Even if you survive to insist crime pays in the long run, do the spoils reconcile a corrupted soul? —Kimble

34. “Ignorant Sh*t,” Featuring Beanie Sigel (2007)

Producer: Just Blaze

Leave it to Jay to turn “This is that ignorant shit you like / N---a fuck shit ass bitch trick plus ice” into a luscious, indelible hook; leave it to Jay to turn “Scarface the movie did more than Scarface the rapper to me” into a perceptive attack on the double standard between prudish calls for censorship in film (which pop up rarely) and prudish calls for censorship in rap (which pop up all the g*ddamn time). That “Ignorant Sh*t” is the sneak-attack highlight of 2007’s ostensible movie soundtrack for American Gangster only heightens the effect; Just Blaze’s immaculate beat is audacious enough that this is definitely the second-best rap song to sample the Isley Brothers’ “Between the Sheets.” —Harvilla

33. “Never Change” (2001)

Producer: Kanye West

Jay-Z is a supreme creature of habit. For decades, he’s essentially rapped about the same three things: growing up impoverished, becoming a drug dealer skilled enough to escape said poverty, and all of the things and experiences one can buy when you’re a very good drug dealer turned great rapper. “Never Change”’ is a monument to this thematic stubbornness. The sample of David Ruffin singing “never, never, never, never change,” only punctuates Jay’s eternal desire. The drug dealer turned mogul never wants his audience to forget that he’s the ideal of a street hustler no matter how much time passes.

Now this is the part of the blurb where I insert a long diatribe about Jay admitting he lost 92 bricks and try to parse the veracity of his story. But the 92 bricks story is far more interesting for how Hov sees himself than the specifics of the event. As a song dedicated to a former drug dealer’s arrested development, “Never Change” feels prophetic. After The Blueprint, Jay would slowly morph into the living embodiment of capitalism. He could sell anything if given a chance. So when he describes crawling back to the top after losing 92 bricks (or at least $92,000 worth) it unfolds like a four-bar parable. To truly succeed against adversity, according to Jay, all you need is “A-1 credit,” five days, and a little bit of tenacity. —Holmes

32. “This Can’t Be Life,” Featuring Scarface and Beanie Sigel (2000)

Producer: Kanye West

For all the big, pop-y mainstream hits that helped make Hov an international superstar, many of which appear higher up on this list, he was frequently at his best when he stripped everything down and exposed his innermost thoughts. That’s what we get on “This Can’t Be Life”—Jay digging into the crates of his experience to expose the pain of his past while voices wail in the background. The song is heavy and unvarnished, full of heartbreak and anguish. And in that despair that he shares with us, there is no small amount of truth. It’s a raw and real audit of his life, the kind of vulnerability he doesn’t often offer. There’s undeniable beauty in that. It should also be noted that it features Philadelphia’s own Beanie Sigel, which naturally makes it a classic. —Gonzalez

31. “Izzo (H.O.V.A.)” (2001)

Producer: Kanye West

Kanye West was still just a try-hard, kinda-rando Roc-A-Fella producer back in 2001 when he waited for an opportune moment to put one of the beats he’d been working on—which sampled the Jackson 5’s “I Want You Back”—in front of Jay-Z. Within minutes, an inspired Jay-Z was to-the-izz-ing in Kanye’s face, and “Izzo (H.O.V.A.)” was born. The third track and lead single on the soul-centered album The Blueprint, the lyrics to “Izzo” described Jay-Z’s dealer days (“was herbing ‘em in the home of the Terrapins”) and his legal travails (“not guilty, y’all got to feel me”). The music video featured a Latrell Sprewell jersey and cameos from Outkast, Destiny’s Child, and Nelly. (Oh, and Kanye, about whom the video director thought: “Who is this guy?”)

The song would become Jay-Z’s first top-10 hit, and he was ready to take the leap. “Show them how to move in a room full of vultures,” he sang. “Industry is shady, it needs to be taken over / Label owners hate me, I’m raising the status quo up.” (Speaking of shady industry: When Jay-Z debuted “Izzo” at the BET Awards in the summer of 2001, Cam’ron, who was watching on MTV, was caught off guard, having been previously told by Kanye that the beat was for the Dipset leader.) Eight years later, Jay-Z’s “Empire State of Mind” would be considered an anthem for New York City. “Izzo,” though? That’s the anthem. —Baker

30. “Otis,” Jay-Z and Kanye West Featuring Otis Redding (2011)

Producer: Kanye West

Instead of a blurb, can I just embed Funkmaster Flex taking 22 minutes to premiere “Otis” in 2011?

No? OK, fine: This song is a triumph. It is a peak. It is Jay-Z and Kanye West letting all of you know, once and for all, that they won. They won more than you will ever win, wearing better watches while doing it than you could ever afford. In fewer than three minutes, on top of a searing, chopped sample of Otis Redding’s “Try a Little Tenderness,” the erstwhile partners pronounce their victory with god-like scale. Jay invented swag. Ye pulled up in his other other Benz. Jay called the paparazzi on himself. Ye writes his curses in cursive.

There’s always a backlash, and a decade removed from “Otis,” it’s not hard to see the follies of luxury rap. But if Jay and Kanye were the ones who popularized the trend in hip-hop, at least they were also the ones who killed it by taking it to its most grandiose conclusion. But more to the point, how can you hear the conquering screams at the end of this song and not immediately remember how fucking fun it was when these two guys were on top of the world? —Gruttadaro

29. “Friend or Foe” (1996) and “Friend of Foe ’98” (1997)

Producer: DJ Premier

“Believe you me, son, I hate to do it just as bad as you hate to see it done,” is quite the line for a 20-something to deliver credibly, but then again everything about the “Friend or Foe’’ saga is built on the hypnosis of performance. It can be a little bit difficult to pinpoint the exact moment when a celestial force is widely recognized as a celestial force and still—in hindsight, at least—it’s even harder not to look at the 109-second display of the first song as something of an intergalactic arrival. “You enterprisin’ though, and I like it,” Jay, giddy to play the Don, assuages his imagined rival before twisting the knife, “But fuck with the big dogs, yo, I gotta bite ya.”

Here’s my question, and I really do mean it earnestly: Whose mans is this? There are a lot of ways to rap (over a Preemo beat is a nice place to start) but find me the folks who are doing this and you can have that spot in Dumbo that Hov still wishes he’d pulled the trigger on. Part 2 carries a bit more grandiosity—smoking guns, shots in the air, copious amounts of sweat—but manages to keep up the nonchalance. That Jay’s no longer competing with the living (“and please yo, tell Big, he’s unbelievable”) may or may not be a part of the performance. —Pryor

28. “1-900-Hustler,” Featuring Memphis Bleek, Freeway, and Beanie Sigel (2000)

Producer: Bink

Even if you accept the premise, the execution is bizarre: “1-900-Hustler,” a riff on a Rap-A-Lot classic, casts Jay, Memphis Bleek, and Freeway as on-demand advisers who will––for an exorbitant fee––coach aspirant drug dealers over the phone, and Beanie Sigel as the surly operator who directs the calls. (One of those callers is then-Roc-A-Fella signee Young Chris, who’s looking to move work because the label won’t pay him his advance money.) Producer Bink, who picked up the Ten Wheel Drive record sampled here for $5 at a garage sale in Virginia, had hoped everyone would rhyme over the beat’s more subdued sections, which ended up soundtracking those interstitial phone calls. Instead the rappers chose to extend the exultant, horn-driven portion Bink had meant for the hook, making each 16 play like a movie’s climax. Jay gives the caller his money’s worth, offering three different courses of action and even feeding him a line that I use to this day in all my contract negotiations: “FYI––I never been robbed in my life.” Despite that (and despite a typically impassioned Freeway verse to bring the song home) this stands as perhaps the only record where Bleek outraps Jay, the Hard Knock Life intro finally realized. His “strong move quiet / the weak start riots” passage in particular, soundtracked by those thunderous horns, is irresistible. —Thompson

27. “Imaginary Players” (1997)

Producer: Prestige

No one loves telling you how much better their life is than yours quite like Jay-Z, and “Imaginary Players” is his magnum opus of stuntin’. He talks about how he makes more money than you, how he has more jewelry and houses than you, and how he will take your girl with a better car than the one you strived your whole life to get. Hov raps like he’s trying to balance inspiring the next generation with covering up his insecurities with luxury items. On the one hand, he’s dropping gems on the music business, encouraging folks to go independent. But on the other, he’s talking about how he was the first to everything, demanding credit for his contributions, garnering a collective, “We get it, bro, you’re the best.” This results in a hilarious crescendo in which Jay-Z creates a scenario where he educates a man on the monetary difference between a Range Rover 4.0 and a 4.6. In perfect Jay-Z fashion, he has everything and never wastes an opportunity to tell you how and why he got it. —Murdock

26. “Feelin’ It,” Featuring Mecca (1996)

Producer: Ski Beatz

Jay-Z takes a more introspective approach to this record. He raps like he’s on the last day of vacation, going through memory lane and talking about a life he once lived. But the biggest takeaway from the song is the first bar on his second verse: “Even if it ain’t sunny, hey, I ain’t complaining / I’m in the rain doing a buck-forty hydroplaning.” It’s one of the rare moments it seems Jay isn’t talking at you when giving advice. This feels pure and timeless, and it will always get a relisten from me. —Murdock

Photo by Theo Wargo/WireImage

25. “Can’t Knock the Hustle,” Featuring Mary J. Blige (1996)

Producers: Knobody, Nomad, Dahoud Darien, Sean C

Jay Z recorded two albums with R. Kelly. They went on tour together and everything. It was a notorious disaster. Ty-Ty sent Kelly to the hospital, and Kelly got kicked off the tour. Also the albums themselves were pretty bad. Jay should’ve done all this with Mary J. Blige instead. It would’ve made a lot more sense and had a much stronger basis in Jay’s style and strengths as a slick-talking partner to R&B women—not just Beyoncé and Beyoncé alone. Oh well. We’ll always have “Can’t Knock the Hustle,” an unbeatable reminder of Jay’s foundational savoir-faire and pop-eloquence years before Reasonable Doubt at last went platinum and Jay was the biggest rapper in the world. —Charity

24. “Guess Who’s Back,” Scarface Featuring Jay-Z and Beanie Sigel (2002)

Producer: Kanye West

“Talk to me, man!” That’s the sound of unvarnished confidence. In the summer of 2002, Jay was the center of the rap universe. Still basking in the afterglow of The Blueprint and acting as an adviser, ghostwriter, and shadow impresario at Def Jam, he started posting up in unexpected places. First, on Cam’ron’s Def Jam debut in a surprising union of casual giants. Then in a bizarre and misguided collaborative album with R. Kelly. Then, on Scarface’s first non-Rap-A-Lot album release, where he turned Face on to a few new producers, among them a promising protégé named Kanye West, who looped this exquisite flip of the Originals’ “Sunrise” and layered it over Dr. Dre’s “Xxplosive” drums. “Guess Who’s Back” helped introduce Face to a legion of East Coast loyalists, but it’s ultimately Jay’s show—he ad-libs the intro and wrote the hook, plus maybe even Face’s verses. Alongside one of the most iconic and trailblazing artists in rap history, Jay is nevertheless in complete command. It’s a master class in how a feature can become a leading man performance. —Fennessey

23. “Song Cry” (2001)

Producer: Just Blaze

Just Blaze deserves the MVP Award for the emotional heist that is “Song Cry.” Jay-Z tells the story of leaving behind a woman that held him down, only to find out years later that she moved on to someone else. When reading the lyrics without the emotional backdrop that comes with the sample of Bobby Glenn’s “Sounds Like a Love Song,” it’s pretty tricky to see Hov as anything other than a dirtbag in this story. Ol’ girl helped him lease his whip and packed the gun for him back when he was broke. And now he can’t even let a tear fall down his cheek when “mourning” his lost love due to all his machismo.

But something strikes different when you hear him rap over the serenity Just Blaze created with the harp and Bobby Glenn vocals. All of sudden I start to feel bad for the guy that said “I was just fuckin’ them girls, I was gon’ get right back” like his infidelity was an inconvenience as minor as city traffic. The third verse comes to a close, and I’m almost ready to shed a tear for Hov. The women he treated like shit rightly realized that he ain’t shit. Yet somehow, Hov and the beat leave me feeling empathetic as if he was the one being done wrong. —Kermah

22. “A Million and One Questions/Rhyme No More” (1997)

Producer: DJ Premier

Just one year after the release of Reasonable Doubt, Jay-Z returned with In My Lifetime, Vol. 1. To lead off his sophomore effort, he linked up with DJ Premier for the classic album intro “A Million and One Questions/Rhyme No More.” Split into two beats, Jay-Z glides over the first part’s sped-up Aaliyah vocals before seamlessly transitioning into the laid-back boasts of “Rhyme No More.” It’s a young Jay-Z still on the rise after the critical success of Reasonable Doubt, and despite its modest commercial returns, he’s now dealing with the unwanted attention that’s followed his newfound celebrity.

Jay-Z’s confidence nearly bursts through the speakers as he begins with the question: “Is he gonna ever fall off?” Though Vol. 1 has its share of missteps, he proves from the album’s opening that his debut was no fluke, and that he had no intentions of going anywhere. With Jay-Z still honing his rhyming craft while beginning to tinker with a more commercial sound and appeal in his music, the Brooklyn rapper was only getting started. —Chin

21. “Dirt Off Your Shoulder” (2003)

Producer: Timbaland

Let’s take a second and watch Jay’s reaction to the first time he heard this beat, courtesy of the Fade to Black documentary.

That look—that stank face—is the highest possible praise anyone can pay a beat. Timbaland has been inspiring similar grimaces for artists and fans of all walks for nearly 30 years, but he’s reserved some of his filthiest work for Jay. There’s of course “Big Pimpin’,” but also “Snoopy Track,” “Hola’ Hovito,” “The Bounce,” “One Minute Man,” “Picasso Baby,” “Hey Papi,” and a handful of others. “Dirt Off Your Shoulder” is one of their finer moments together. That’s a testament to not only Tim’s skills, but also Jay’s ear—plus his entire face, which seems to recognize a classic instantly. —Sayles

20. “Intro” (2000)

Producer: Just Blaze

The best Jay-Z verses are marked by hairpin turns: quick switches in syntax or tone, phrases broken at unexpected points to set up a surprising rhyme scheme. This technical virtuosity is sometimes framed––including by Jay himself; see the second verse on “Moment of Clarity”––as being in direct competition with the confessional, the introspective, the true. But the Dynasty intro is a moment of total synthesis, a time when the acrobatics of writing and performance wring something new out of Jay, pain and defiance in equal measure. See, for example, the way he pitches his voice so that every syllable of that Malcolm X line comes through in the same register: It makes the paranoia and the gun-gripping seem rote, inescapable. That’s followed immediately by …

Never read the Quran or Islamic scriptures
Only Psalms I read was on the arms of my n----s
Tattooed, so I carry on like I’m non-religious

… where “tattooed” is an almost-shouted interjection that underlines the image a thousand times. The verse would be one of Jay’s signature turns no matter the context, but it comes at the beginning of an album, after 75 seconds of breathless buildup. And to think the record is riddled with imperfections: The mastered version of this song bears little resemblance to what Just Blaze imagined, its samples competing with one another where one should be allowed to breathe, the vocal looping where it shouldn’t. None of that matters––the cacophony is the point. —Thompson

19. “So Ghetto” (1999)

Producer: DJ Premier

It’s hard to believe you could fit so much skill and swagger into four minutes. I first heard this song in my teens and it grabbed me, and still grabs me, for two reasons. One of those is the brilliance of the storytelling. I have always seen Jay-Z as a screenwriter, someone like David Chase composing his own version of The Sopranos, and the way that he crafts images is unique. Most of his fellow screenwriters would say, “You think you’re Superman so I’m going to show you how powerless you are by making you attend your friend’s funeral.” They’d be that literal, fearing that otherwise you wouldn’t get the point. But Jay-Z says, “We spray corners, stand there like you got a cape on ya, fine / You’ll be wearing a black suit a long time / I put your crew in hard bottoms / The priest is like, ‘God’s got him / He never did nuttin’ to nobody but them boys shot him.’”

The second is for the shamelessness, with Jay-Z refusing to date a woman who can’t understand why he is rich but still wearing a durag. That just wasn’t what you did—you grew up, got money, and smartened up, right? But Jay-Z said, to hell with that, and that felt heroic. —Okwonga

18. “N---a What, N---a Who (Originator 99),” Featuring Big Jaz (1998)

Producer: Timbaland

Certain organisms are born to adapt. Whether it’s in lightless aquatic trenches, perched near the ash-ridden walls of volcanoes, or surviving in the recesses of space, certain life forms are built to survive. Perhaps Jay-Z’s most undervalued trait is this natural inclination to persist across eras and trends at any cost.

Before the perfected faux-mafioso drug kingpin persona of Reasonable Doubt, Jay-Z was a shy and skinny kid standing next to one-time mentor Jaz-O in his first credited appearance, 1990’s “The Originators.” Instead of the suave and precise nature of Jay’s future delivery, “The Originators” features the gangly Marcy Projects MC in his own words, “Wreckin’ and wreckin’ in seconds less than speeds of light.” Jaz-O physically has to pull Jay into the frame to perform his verse at one point in the music video.

Eight years later, Jay released “N---a What, N---a Who (Originator 99),” a spiritual successor to “The Originator” as if to prove the drastic nature of his artistic transformation. Instead of rapping about “Exciting the mic much to the delight of millions of Nubians,” listeners are regaled with stories about Jay’s condom-filled condo where rapping and sexual intercourse are the only two activities allowed. The double-time flow of yore is intact, but Jay’s confidence elevates the one-time gimmick into high art. By the time Jaz-O appears, the point is made. The former student hasn’t just become the master, but ripped up the curriculum and built a university on top of it. Even the most talented of Originators can be bested. —Holmes

17. “Streets Is Watching” (1997)

Producer: Ski Beatz

Jay-Z opens “Streets Is Watching” with the lines: “Look, if I shoot you, I’m brainless / But if you shoot me, you’re famous.” He raps about the shifting dynamics of his life after entering stardom, with his every move now being watched closely by the world, waiting for him to slip up and make a mistake. Following a rare playoff loss to the Raptors in 2016, LeBron James cited the quote when he was asked about retaliating against opposing players after hard fouls, not long before he led Cleveland to its first championship. Expectations change when you’re the king.

There’s an added irony in such a raw song about drugs, crime, and the watchful eye of the streets, as it’s nearly impossible to find an uncensored version of “Streets Is Watching” due to an issue with the song’s Labi Siffre sample. That it has remained a classic nonetheless is a testament to Jay-Z’s masterful performance over the Ski-produced beat, as the In My Lifetime, Vol. 1 standout later served as the title track for his 1998 film of the same name. —Chin

16. “My 1st Song” (2003)

Producers: Aqua, Joe “3H” Weinberger

When Jason Voorhees returned to the franchise in 1986’s Friday the 13th Part VI: Jason Lives, did it diminish the impact of his dramatic demise at the end of 1984’s Friday the 13th: The Final Chapter? I would argue no. The same logic applies to this elegiac origin story, intended as a farewell to his fans at the end of Jay-Z’s sustained reign of greatness. Jay, of course, came back wearing the 45. But before leaving, he departed on the tailwind of one of his most graceful flows, a stuttering dance through the raindrops of Aqua and 3H’s cascading beat. Fittingly, Jay unfurls a falsetto and underlines his penchant for contorting aphorisms. It’s one of the great mic drops that doubles as a statement of aspiration. It certainly inspired one notable contemporary to keep pushing on. “My 1st Song” opens with a reflection from his late friend Biggie Smalls to “stay busy, stay working.” Jay couldn’t stay away. —Fennessey

15. “I Just Wanna Love You (Give It 2 Me)” (2000)

Producer: The Neptunes

It seems as though Jay-Z has always been part of—and simultaneously ahead of—the pop culture curve. These days, there’s plenty of people who want to talk about art—or music or life or relationships—as a vibe, but way back in 2000 that’s exactly how Hov described this track: “It was just the vibe. The vibe of everyone in the studio.” The way Jay recalled the creation, “people were singing it by the time the second hook came on.” All these years later, I defy you to make it past the first hook—or the first few lines—before you join in. No reasonable human with ears can hear that song and resist crying out “I’m a hustler, baby.” By the time we get to “give it to me,” it’s a call to action that requires everyone to demand that sweet, that nasty … well, you already know the rest. You’ve been singing it for decades. You’re almost certainly singing it right now. —Gonzalez

14. “D’Evils” (1996)

Producer: DJ Premier

A striking feature of Reasonable Doubt is just how world-weary Jay sounds. He’s just entering his late 20s, so he is comparatively old in rap terms, but he still speaks with the wisdom of someone 30 years older. In three lines he sets out the premise of every single crime drama that ever graced HBO: “Whoever said illegal was the easy way out / Couldn’t understand the mechanics / And the workings of the underworld, granted.” The whole track has the feel of a sinner who goes to his local priest for confession, and then upon leaving the church immediately continues his wayward behavior. And, as Jay-Z confesses, he does so with the deceptively simple change of flow that is his hallmark. “Liquor’s invaded my kidneys / Got me ready to lick off, mama forgive me / I can’t be held accountable, D’Evils beating me down, boo / Got me runnin’ with guys, makin’ G’s, tellin’ lies that sound true.” It’s the height of self-awareness (I am broken) and self-denial (I have no control over my brokenness) that is at the heart of so much of Jay-Z’s best work. —Okwonga

Photo by Frank Micelotta/ImageDirect

13. “Can I Get A…,” Featuring Amil and Ja Rule (1998)

Producers: Irv Gotti, Lil’ Rob

Truly impressive that the missing two words in this song title were “Fuck You,” given that this stupendous trunk-rattler (God bless coproducer Irv Gotti) and Rush Hour soundtrack highlight (God bless Chris Tucker and Jackie Chan) snuck into the top 20 of the Billboard Hot 100 and cemented Jay-Z as a towering commercial threat who sounded immortal and made anybody on the track with him sound immortal, too. (God bless Amil and Ja Rule.) Eventually slotted onto 1998’s Vol. 2 … Hard Knock Life, “Can I Get A…” is a bass-heavy and insidiously serpentine pop earworm that makes Jay sound dreamy even when he’s starting his verse with the line “Can I hit in the mornin’ without givin’ you half of my dough?” And Amil, meanwhile, makes for a fantastic foil: “Ambition makes me so horny” is all late-’90s Jay ever needed to hear. God blessed him most of all. —Harvilla

12. “N----s in Paris,” Jay-Z and Kanye West (2011)

Producers: Hit-Boy, Kanye West, Mike Dean, Anthony Kilhoffer

Anyone whose ears don’t instantly perk up at the synthy loop in “Paris” or feel compelled to recite Hov’s “BALL SO HARD!” ad-libs is suspect in my book. A decade has passed since “Paris” dropped, yet it still bangs like you’re hearing it for the first time. It’s a perfect hype song for any situation—attending a sporting event, prepping for a game, studying for a final, cleaning the kitchen, etc.

Considering all of Watch the Throne’s call-and-response tracks between Hov and Kanye, “Paris” endured as the most exciting, and it’s easily one of the most fun songs in Jay-Z’s entire catalog. The Blades of Glory sample remains objectively witty. (“No one knows what it means, but it’s provocative” could describe listening to “Paris” for the first time.) “Paris” also comfortably bridges any generational gaps that might exist between Jay-Z’s listeners. It doesn’t matter whether you’re Gen X, Gen Z, or a millennial, “Paris” is a recognizable hit made for everyone to enjoy while rhyming fun-ass bars (“Psycho, I’m liable to go Michael, take your pick / Jackson, Tyson, Jordan, Game 6”) and feel like they “BALL SO HARD!,” regardless of what you think of the record’s final minute. —Jones

11. “Brooklyn’s Finest,” Featuring the Notorious B.I.G. (1996)

Producers: DJ Clark Kent, Dame Dash

“Brooklyn’s Finest” was never supposed to happen. According to Clark Kent, Jay was ready to record a solo song to the beat before Biggie heard it. Then Big demanded he get a spot on the track, despite not knowing Jay. Kent brought Big to the studio where Jay was set to lay the track down and asked the Bad Boy MC to wait in the car while he worked out the details. But even with the opportunity to get one of the most popular rappers in the world on Roc-A-Fella Records’ first release, Jay’s business partner Dame Dash initially balked at the idea of handing over the tape of royalties and publishing that would require. Eventually, they came to an agreement and Kent retrieved Big from the car. Jay rewrote his rhymes on the spot—in his head, as is his MO—to the shock of Biggie, who took another two months to come back to record his parts.

You’d never guess these two didn’t know each other beforehand based on the chemistry they show off on “Brooklyn’s Finest.” The multi-times-platinum Biggie and the upstart Jay-Z sound like peers as they trade bars over Kent’s infectious piano beat (sequenced as a five-bar loop, something virtually unheard of in hip-hop at that point). Big had lent out his talents to plenty of lesser-known rappers during his prime. None truly held their own. (No disrespect to Pudgee Tha Phat Bastard; some disrespect to Tracey Lee.) But Jay sounds like Big’s equal here (even as Big takes a not-so-subliminal swipe at Tupac Shakur’s claims to have slept with Big’s wife, Faith Evans). Perhaps this is the moment we should’ve known Jay would be a star.

The pair would become close over the remaining months of Big’s life—they had plans to start a supergroup called the Commission and Jay popped up on Life After Death in 1997. After Biggie died, Jay sought to further align himself with the image of his fallen comrade, name-checking him whenever possible and quoting heavily from Big’s catalog. Today, it’s impossible to consider Jay’s origin story without thinking of the role Biggie played in it. And to think, it may have happened if Big had never heard that beat. —Sayles

10. “U Don’t Know” (2001)

Producer: Just Blaze

Before Jay demands “turn my music high,” the rest of us already have done so. The track goes from zero to holy shit before it even truly begins, requiring that your head move in unison with the very first explosive beat. And then Jay speaks, spitting so many lines at the listener with such force it’s like being launched by a rocket thundering toward a stratosphere only he can reach. When Jay goes on an extended coke/Wall Street metaphor, he concludes by rightly surmising that “this is worse than the Dow Jones, your brains are now blown.” And that’s just the opener.

He’s at his best from start to finish—and what’s more, he knows it. It’s a masterwork that offers all the hallmarks of a classic Jay track: an undeniable, cranked-up, speaker-thumping sample of Bobby Byrd’s ’70s classic combined with an industrial-strength dosage of bravado. Here, yet again, he responds to the critics who tell him “You don’t know what you’re doing” with an immediate reply: “Yeah I do.” Of course, that one-man call-and-response is mere misdirection. What Jay really thinks of himself and his abilities is found in five words that he fires off in individual one-round bursts so we all get the message: “Motherfucker. I. Will. Not. Lose.” He rarely has. —Gonzalez

9. “99 Problems” (2003)

Producer: Rick Rubin

There’s a scene in the 2004 documentary Fade to Black when Jay-Z shows up at Rick Rubin’s L.A. studio (in a Von Dutch shirt!) eager to recapture what he calls hip-hop’s “golden years.” Rubin meets his request with a rumbling, 808-rich, verge-of-a-bar-fight beat, which sends Jay into his signature fugue state and results in a parable about a drug dealer who gets pulled over by a cop. Jigga proceeds to rap the voices of both characters, casting the drug dealer as the cunning hero and the cop as a simple racist. “Might be something special,” he mutters, exiting the booth. “Some old-school storytelling shit.”

I don’t really have to tell you that it was, in fact, something special. The Ice-T inspired hook—“I got 99 problems but a bitch ain’t one”—boomed from practically every car, iPod, and clunky Dell laptop that spring, its double meaning simultaneously turning it into talking-heads bait and summer anthem. Beyond the clever wordplay, Jay-Z was telling the world what it was like to be Black in America, a point made all the more raw when paired with a controversial music video in which he was shot to death in the Brooklyn projects where he grew up. A decade later, the footage pales in comparison to the gruesome real-life social media videos of police violence toward Black Americans—proof that Hova was truth-telling long before most white Americans really cared to listen. —Bereznak

8. “Public Service Announcement (Interlude)” (2003)

Producer: Just Blaze

Imagine if Jay-Z never wore that Che Guevara shirt. Imagine if journalist Elizabeth Méndez Berry hadn’t called him out—to his face—for the incongruity of wearing it with a Jesus piece. And imagine if he weren’t still thirsty for one more Just Blaze beat for The Black Album—even as it was on the verge of being mastered. Without that alignment of circumstances, “Public Service Announcement”—the interlude that’s become one of the most unconventional highlights of Jay-Z’s catalog—might not exist. First, there’s the production: the crisp pop of Just Blaze’s snares, the wailing organs, and the chilling piano keys lurking in the background. Then there’s the structure: no hook, an introductory address from Just Blaze himself, and two verses of Jay-Z talking shit as an interruption from your regularly scheduled programming. Jay-Z is no revolutionary (“I also wasn’t a Marxist like Che—the platinum Jesus piece made that pretty clear,” he writes in Decoded), but the “retiring” legend flexed his eagerness to exit with a bang by any means. —Kimble

7. “Hard Knock Life” (1998)

Producer: Mark the 45 King

Before Vol. 2, Jay was more of a rap hypothetical than a rap inevitability. As much as Reasonable Doubt is now seen as canon, Jay’s debut basically came and went. Even Hov on “Hard Knock Life” references how slept on the now-classic is when he says, “Didn’t really appreciate it until the second one came out!” His sophomore offering, Vol. 1, was a moderate improvement in terms of commercial success, but the album didn’t do much to advance the cause of Jay-Z as heir to the throne vacated by Big. It wasn’t until “Hard Knock Life” that Jay-Z finally announced himself as the new ruler of NYC rap. It’s a song dedicated to the downtrodden, to urban lifers in prison and “chicks wishin’ they ain’t have to strip to pay tuition” all over a sample from Annie. It’s Jay-Z’s coming out party. —Lambre

6. “Big Pimpin’,” Featuring UGK (1999)

Producer: Timbaland

Best Timbaland beat ever? No argument here. Best marriage between a New York City institution and a Texas institution ever? Well, Beyoncé’s from Houston, but in 1999 the pure rapture of Jay-Z and Port Arthur deities UGK on the same record—on the best Timbaland beat ever—was impossible to overstate. Best Jay-Z song in which Jay-Z has the worst verse? That depends on how impressed you are by the way Bun B rhymes scenario with scary ho. Tim and Jay would (successfully) defend “Big Pimpin’” in court for the next two decades and it was still worth it; you have likely heard “Big Pimpin’” 50,000 times and I’ll bet you still love it, still bow down in its presence, still jump on the nearest couch with both feet in its presence. Jay writes in his 2010 book Decoded that the song was inspired by the 1973 blaxploitation classic The Mack and contrasts his cartoon-fantasy life as a pimp to his relentlessly grim real-life past as a drug dealer, which casts a pall even over the girls in the back of the truck laughin’ it up: “One way or another, in real life, the laughter is going to end,” he observes. “But not in this song.” —Harvilla

Photo by Al Pereira/Michael Ochs Archives/Getty Images

5. “Heart of the City (Ain’t No Love)” (2001)

Producer: Kanye West

Jay-Z’s mornings sound terrible. In Hov’s Groundhog Day, he repeatedly wakes to news that another one of his favorite musical groups has broken up and that some new person or group hates him. Jay tries to take this Sisyphean experience in stride, backed by a sample of Bobby Bland informing the world-weary MC that there indeed is no admiration in the city or even the town. All our protagonist can do is wonder aloud at the end of each verse, “Where’s the love?”

“Heart of the City (Ain’t No Love)” is a far more existential song than the soulful, Kanye-produced track seems on the surface. The aforementioned city is closer to an amorphous idea than a physical destination. By 2001, Jay-Z was at pop culture’s center. Even amid feuds, empire building, and a terrorist attack that overshadowed the release of his sixth studio album, Jay was unstoppable.

“Heart of the City” splits the difference between victory lap and therapy session. A motley crew of antagonists—young fucks, sensitive thugs, bird-ass n----s, soundboys—pray on Jay’s downfall, despite the rapper’s insistence that he merely wishes for the simple things in life:

I don’t want much, fuck, I drove every car
Some nice cooked food, some nice clean drawers

No amount of bank statements, records sold, or summers being held down can stop the onslaught of negativity. Over the cinematic guitar riff and soaring background hums, Jay takes it all in stride. He has an answer for every detractor, a barb ready for every slight. “Heart of the City” is the sound of triumphant pettiness and an admission that even when Jay can’t receive love, he can still command respect. —Holmes

4. “Takeover” (2001)

Producer: Kanye West

Telling the rest of hip-hop to go fuck itself isn’t exactly the type of thing that’s generally associated with stolidity. And yet, when Jay did it on “Takeover” he made it impossible to arrive at any other conclusion but that he was both above it all and, at the same time, prepped to put each and every one of his competitors in their proper place. He dismantled Prodigy, of rock-you-in-the-face-stab-your-brain-with-your-nose-bone fame, with a succession of daggers ranging from the belittling (“You little fuck, I got money stacks bigger than you”), to the eristic (“We don’t believe you, you need more people”), to the metaphysical (“I’ll detach you / Mind from spirit, body from soul”). And, to think, this was merely the warm-up.

The mythology behind the track is incredible in hindsight and just as trite. In the wake of Christopher Wallace’s death, a cold war brews, starting first with Jay’s and Nas’s adjacent crews before eventually bubbling to the surface between the two rap titans themselves. For several years, they spar over who is more deserving of rap’s crown and engage in a series of escalating attacks on each other’s masculinity, ranging from homophobic slurs and death threats to schoolyard taunts and cuckolding accusations.

The song is an exhibition in getting under your opponent’s skin. Whether clowning a guest verse on the much-maligned posse cut “Oochie Wally” (“Matter of fact you had the worst flow on the whole fucking song”), questioning the authenticity of his Escobar persona (“You scribbled in your notepad and created your life”) or highlighting the rapper’s inconsistent discography (“That’s a one-hot-album-every-10-year average”)—again and again, Jigga finds a way to hit Nas where it hurts. The facts of what occurred afterward—“Ether” and the immediately disavowed “Supa Ugly”—do little to change that Jay made the single most naturally gifted writer in the history of rap look like a stumbling, hurt has-been. And he did so without losing his cool. It’s still hard to tell whether this affect was the product of gamesmanship, acting, or a kind of sociopathic coldheartedness. As with everything Hov, the winds blow in all directions. —Pryor

3. “Can I Live” (1996)

Producer: Irv Gotti

Upon revisiting what is now damn near universally accepted by the Heads as Jay-Z’s single greatest song, it’s not hard to understand why people dismissed Jay as another drug-dealing fantasy proprietor at the time. “Can I Live” finds Jay being quite frank about the allure of breaking the law (as he would later put it on another classic song)—the fast living, the escape from the ghetto, the lavish trips to Vegas. But at its core, “Can I Live” is about the deeper costs of living a life outside of the bounds of proper society: the insomnia, the inability to achieve true intimacy with anyone out of a need to keep all newcomers at arm’s length, the volatility of drug markets and never knowing when the next drought may come. It’s all there in the title of the track. He does this all while spitting the slickest raps ever uttered on a microphone. Irv Gotti’s production is both regal and melancholic and Jay’s bars echo this duality to perfection. —Lambre

2. “Where I’m From” (1997)

Producers: D-Dot and Amen-Ra

Jay-Z opens his first album on the highway, beaming out a sunroof, en route to some anonymous I-95 town he’ll take over in a weekend and abandon just as quickly. He always rapped like a New Yorker—over time his tics came to seem like the city’s—but he would describe the beaches he’d escape to, the trips to London with Jaz and the ones to Vegas where he washed his money. He made a song called “The City Is Mine” that sounds for all the world like Virginia Beach. It wasn’t until the end of his second LP that he aimed to immerse the listener in the neighborhood where he grew up. When he finally did, it was ruthless, gnashing, and as unwelcoming as one could possibly hope.

“Where I’m From” begins with taunts to Prodigy for claiming the Marcy homes and TV news crews for being scared to do the same; it asks the listener to imagine making out a will at 18, and then a pool of blood growing around Jay’s body. The details are entrancingly specific: the hand-held weight scales for small-time hustlers who don’t need anything heavier, the sweaters lifted from department stores and hawked on curbs for half the price. These populate a beat—an Yvonne Fair song warped to ghoulish proportions—that is mostly menace and negative space, one that Jay alternately burrows deep inside and scoffs at, as if its measures were half-hearted suggestions.

That tendency to dance on top of the drums makes Jay’s raps seem conversational in the way your slickest friend has conversations—laughing, backtracking, drawing a straight line from slit throats to new Porsches. It would be dazzling were it not so unrelentingly grim. Through all of this runs an undercurrent of spiritual torment: At one point, Jay dares God to strike him down on the spot if any of his reporting is exaggerated. That was 24 years ago. —Thompson

1. “Dead Presidents” / “Dead Presidents II” (1996)

Producer: Ski Beatz

In this telling of the myth, “Dead Presidents” wasn’t supposed to be the one that lasted. In Decoded, his 2010 autobiography, Jay-Z wrote that he and Dame Dash tried pushing the single on Funk Flex shortly after they pressed it independently in early 1996, but they got nowhere. With the help of Irv Gotti, the biggest DJ in New York eventually bit, but Irv had a recommendation: Flip the record over and play the B-side, “Ain’t No N---a,” the “Seven Minutes of Funk”–sampling Foxy Brown feature that seemed destined for greater club and radio play. For a while it worked. Jay recalled watching Flex play the song seven times straight during one night at the Tunnel, and the crowd erupted every time. The introspective “Dead Presidents” may have been the better song, but the better song doesn’t always make the bigger hit.

“Ain’t No N---a” would land on the Nutty Professor soundtrack and earn Jay modest MTV play, but it’s luster soon faded—it peaked at no. 50 on Billboard and receded from the commercial consciousness as the blockbuster sounds of Bad Boy tightened their chokehold on the charts. The A-side to the single, however—that was something to build off. Ski—whom Jay knew from his Original Flavor days—built the beat around a Lonnie Liston Smith sample, drums from A Tribe Called Quest remix, and a vocal clip for Nas’s “The World Is Yours” that the producer placed simply because he liked the way it sounded. The result was something that rang simultaneously triumphant and melancholic, bittersweet to its core. It was the exact thing Jay needed to bring his new style to life—to allow him to transition from tongue-twisting speed rapper to street documentarian.

So much of the Jay-Z story is about a myth: the prolific hustler who just happened to be preternaturally gifted at rapping, the unheralded MC who became the heir to Big’s throne, the businessman who was a business unto himself, the player who settled down only when he landed the flyest chick in the game. “Dead Presidents” certainly plays into the myth-making—its video features him, Biggie Smalls, AZ, and Lil Cease playing Monopoly with actual cash—but it still feels shockingly real. That’s a credit to Jay’s pen, which has arguably never been tighter, and his flow, which he was in the process of making more conversational, but still contained the hallmarks of the rapid-fire delivery that first got him noticed on an underground level. If he had never put out another single, it would’ve been enough to make him a legend among a certain subsect of rap fans. Hell, the second verse alone would have been enough to make him an icon.

When Reasonable Doubt came out later that year, those verses were gone. Sitting there at Track 4 was “Dead Presidents II,” a song with the same beat, but new lyrics. They’re even more stunning. Take the moment from the opening verse when he briefly turns to the horrific vision of a friend who had been shot. An entire world exists within these six bars:

Hospital days, reflectin’ when my man laid up
On the uptown high block, he got his side sprayed up
I saw his life slippin’, this is a minor setback
Yo, still in all we livin’, just dream about the get-back
That made him smile, though his eyes said “pray for me”
I’ll do you one better and slay these n----s faithfully

Jay-Z wasn’t the first person to rap about selling drugs, but along with Biggie, he was among the first to document its spoils and stresses with a novelist’s eye. Nobody had done it better, and perhaps nobody has done it better since. For all the credit Nas receives for his talents as a scribe, the Jay-Z of “Dead Presidents” is every bit his equal—there’s a reason Barry Michael Cooper calls him the Proust of the Projects. But Nas always fashioned himself the hero. The Jay-Z of this era was all too happy to play the bad man, as long as the villain wins. It’s the difference between “One Love” and “D’evils.” And we see that character—a Sam Rothstein in a world of Tony Montanas—come to life for the first time in these lyrics.

“Dead Presidents,” the runaway no. 1 in these rankings, would feature prominently in the Jay myths to come. When he and Nas fell out, the chorus to “Dead Presidents” became a focal point. At one point—either while recording his would-be swan song or when he was returning from it—he tried cooking up a Part 3. “Friend or Foe” intro aside, it’s always seemed as though there’s part of Jay that wants us to forget that he existed before Reasonable Doubt—that he never popped up in the “Hawaiian Sophie” video, that his Das EFX phase never happened. “Takeover,” the atom bomb he detonated on Nas because of their complicated history dating back to “Dead Presidents,” conveniently ignores those earlier eras. In Jay’s self-created mythos, the clock starts with the divine intervention of “Dead Presidents.” And who wouldn’t want to give the appearance of having arrived fully formed as one of the sharpest writers rap has ever seen?

For anyone else, it may be a little too neat of a narrative. But for Jay-Z, the best tales have always combined reality with just a touch of fiction. Or, in his words, “I’ll tell you half the story, the rest you fill it in.” Thankfully we flipped the record back over and let him start building the myth. —Sayles

Paul Thompson, Julian Kimble, and Musa Okwonga contributed to these rankings. Thanks to Jeff Weiss and Brandon “Jinx” Jenkins, both of whom took part in the voting, and to Daniel Chin for research assistance.