Comedy in the ’90s, Part 3: The Bad Boys of ‘Saturday Night Live’

Nearly 30 years ago, a handful of smart people set out with one mission: to make some silly movies. What followed was a true golden age of Hollywood comedy that saw the arrival of megastars still with us today, a commercial explosion, and then, an eventual splintering that changed the genre forever. Welcome to Part 3 of Comedy in the ’90s, our six-part series documenting this decade-defining boom in all of its sophomoric glory.

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As the clock neared 1 a.m. on an evening in May, Adam Sandler walked onto Saturday Night Live’s Studio 8H stage alone. This would not be for a sketch, or even a bit of stand-up. Instead, Sandler, who was hosting for the first time since being fired from the show in 1995, picked up a black Takamine acoustic guitar and began to play a bittersweet tribute to a late friend.

The first time I saw him he was sweeter than honey
Plaid jacket and belt too tight and he wasn’t even being funny
Then he cartwheeled around the room and he slow-danced with the cleaning lady
He was a one-man party
You know who I’m talking about, I’m talking about my friend Chris Farley

With a thin five o’clock shadow covering his face, the then-52-year-old Sandler seemed to barely make it through the song without breaking down. Accompanied by a video montage of Farley’s greatest hits, the nearly five-minute ballad told the story of Sandler’s larger-than-life friend and former SNL castmate—his most memorable characters, his contradictions, his demons, his humanity, and finally, his place in history.

Hey buddy, life’s moved on but you still bring us so much joy
Make my kids laugh with your YouTube clips or Tommy Boy
And when they ask me who’s the funniest guy I ever knew
I tell ’em hands down without a doubt it’s you

That night, Jonah Hill was watching. “I was like, crying. I was crying,” he says proudly. “Sandler and the Beastie Boys, for our generation, were prime examples of how to be cool.” To boys bar mitzvahed in the 1990s—boys like Hill—the musically inclined, often filthy, laid-back but occasionally volatile comedian was a god. But Sandler’s appeal also extended well beyond overnight camp and Hebrew school carpools. In the mid-to-late ’90s, he was everyone’s favorite class clown, a man-child who could generate laughter with ease.

“He had this charming-Jewish-boy-he-could-be-your-college-boyfriend-guy thing,” says Tamra Davis, who directed Sandler and Farley in Billy Madison. “There was something attractive that I saw in him. He wasn’t just a repulsive guy. He had a heart in this weird way.”

If Sandler was a relatable mensch with the ability to explode for comedic effect, then Farley was his inverse, an intensely hilarious force with the subtle ability to be almost painfully sweet. Built like an interior lineman and nimble like a ballet dancer, he did anything he could to make people laugh. “He would scare me,” Davis says. “That was how his comedy was. He would push it so far to the edge that you didn’t know if he was gonna just crash into the wall or jump off the stage. He wasn’t just a regular, ‘I’m in control’ comedian. He was like Kurt Cobain.”

A decade ago, while filming Funny People with Sandler and Hill, Seth Rogen could barely shake his reverence. “We were like, ‘It’s crazy. He’s right over there,’” Rogen told Parade magazine in 2009. “‘Adam knows our names. That’s awesome.’”

Toward the end of his ode to Farley, Sandler’s voice cracked, and as he strummed the song’s final chord, the SNL audience erupted in emotion. “Not. A. Dry. Eye. In. The. House,” Leslie Jones tweeted that night. It’s not difficult to understand why: The song temporarily opened a portal to a time when the two buddies appeared poised to take over big-screen comedy. But it also served as a stark reminder that only one of them actually did.

After Wayne’s World became a phenomenon in 1992, it spawned a handful of comedies based on Saturday Night Live characters. The problem was that none of those films, with maybe the exception of Wayne’s World 2, were any good. At the same time, some of the series’ most famous alums, who throughout the ’80s carried blockbuster after blockbuster, had started to fade from relevance. Bill Murray did make a masterpiece in Groundhog Day (1993) and Eddie Murphy continued to churn out hits like Boomerang (1992) and Beverly Hills Cop III (1994), but the late-night-to-Hollywood pipeline was clogged. Mike Myers aside, SNL’s status as a launching pad for movie stars was in doubt.

By the mid-’90s, no one was rushing to anoint Sandler and Farley—who, along with Chris Rock, David Spade, Rob Schneider, Julia Sweeney, and Tim Meadows, had joined the SNL cast in 1990. Instead, each had to take a winding path to stardom.

Farley was born in 1964 in Madison, Wisconsin, where he grew up in an Irish Catholic family with four siblings. At a young age, he pulled pranks but usually managed to completely disarm whoever his mischief pissed off. In the biography The Chris Farley Show, his brother Tom tells a story about Chris peeing in cups because he was too lazy to walk from his bedroom to the toilet, a habit his mother, Mary Anne, discovered and informed his father, Thomas Sr., about. The next day at the dinner table, as everyone sat silently waiting for dad to yell at the offender, Tom Sr. took a sip of water. “You’re not gonna drink out of that glass, are you?” Chris asked. “Goddammit!” his dad shouted back.

“Chris knew what was coming,” Tom Jr., who cowrote the biography with Tanner Colby, says in the book, “but he had to get the laugh first.”

At Edgewood High School of the Sacred Heart, Farley played football and resisted teachers’ calls for him to act in plays. When he attended Marquette University, however, his interest in theater grew. On campus, he gained a well-earned reputation as a funnyman and an epic partier. By that point, the late John Belushi had become his hero. Bob Woodward’s Belushi biography, Wired, is said to be the only book he read in college; infamous for focusing more on the SNL icon’s drug use than for his greatness as a performer, it deeply affected Farley. As a teenager, Chris already had begun binge drinking; alcoholism ran in the family. “Chris wasn’t blindly imitating Belushi,” his buddy Jim Murphy says in The Chris Farley Show, “but reading that book validated all the addictions and impulses that Chris already had inside of him.”

For the rest of his life, Farley dealt with addiction. And though his comedic persona wasn’t at all the product of his substance misuse, the two went hand in hand. “He committed to everything he did,” his friend Charna Halpern, cofounder of ImprovOlympic, once told the Chicago Tribune, “and there was no halfway.”

While entertaining his rugby teammates at Marquette, Farley realized that he wanted to pursue a comedy career. He graduated in 1986 after four and a half years—an incident in which he accidentally almost burned down a house with a smoke bomb landed him on probation and forced him to finish his degree at the University of Wisconsin—and then briefly worked for his father. Shortly after that, he gathered up the courage to start performing at Madison’s Ark Improvisational Theatre. Soon, he moved to Chicago, where he shined at ImprovOlympic and then the famed improv theater The Second City. In 1989, he was promoted to the company’s main stage. As a member of the troupe, he began playing a motivational speaker named Matt Foley. Written for him by Bob Odenkirk and named for a college friend, the loud, vulnerable, furniture-breaking character who lived “in a van down by the river!” perfectly highlighted Farley’s talents—and created a considerable amount of buzz. In 1990, SNL’s executive producer, Lorne Michaels, went to Chicago to see Farley in action; just months later, the comedian was hired as a cast member.

The same year, Sandler joined the series as a writer before being added to the cast midseason. Like Farley, he grew up adoring Saturday Night Live—even though he often fell asleep while waiting for it to start. Both comedians came from close families, but their backgrounds differed. Born in 1966 in Brooklyn and raised in Manchester, New Hampshire, Sandler was the performative darling of his Jewish parents, Stan and Judy. “They definitely told me, ‘You can do this,’” Sandler said in January on Conan O’Brien Needs a Friend. “‘You can play guitar, you can sing, you can’t dance.’ I tried to dance a little bit to be the triple threat that my grandmother said I should be. But they said to eliminate the dancing.”

Sandler’s comic timing came in before puberty. At movies as an elementary-schooler, he used to scream at the screen. “I’d always say like five jokes, and there would be four power laughs,” he told the Los Angeles Times in 1994. “And then the fifth one I would say, ‘Hey, nice hair!’ or something like that, and somebody would go, ‘Hey, shut up!’ and then it would just take away the other four jokes I killed on—everyone turned on me.”

By the time he was a teen with dreams of show business, Sandler was unshakably confident. “I was nuts,” he told O’Brien, referring to his penchant for telling his childhood friends that he “was gonna be huge” and that “people are starting to notice.” At the time, no one was. At least not yet.

That gradually changed while he was attending New York University’s Tisch School of the Arts. Tim Herlihy, his college roommate and future writing partner, remembers bonding with Sandler over their love of Caddyshack and Mel Brooks movies. From their sixth-floor dorm room on 10th Street, they’d stick a mirror out the window and direct sunlight onto pedestrians. “Hey baldy!” Herlihy recalls Sandler yelling at one unsuspecting hairless gentleman. “The meaner it was and the more random the victim,” Herlihy adds, “the harder we laughed.”

As an NYU student, Sandler began honing his seemingly anxiety-free stand-up act. “He made comedy cool,” says writer Fred Wolf, who’s been collaborating with Sandler for three decades. “He was able to be effortless, just kind of had a laid-back cool to him. And then when he lost his temper, it got loud. He was hilarious.”

Sandler parlayed his success as a comedian into a few substantial gigs: a role as Theo’s friend Smitty on The Cosby Show and a recurring spot on the MTV game show Remote Control. Then, after graduating from NYU in 1988, Sandler moved to Los Angeles, where he eventually caught Michaels’s eye. The producer enjoyed his silly, mostly impression-free act, a rarity in those days. “I’m great at humping a chair,” Sandler said in 1994. “That’s what got me Saturday Night Live. I was in Lorne’s office humping his chair and he said, ‘My God, that’s funny, you’re hired—seven-year contract.’”

On October 27, 1990, four episodes into his first season on Saturday Night Live, a shirtless Farley shimmied his way into America’s heart. That evening, he and host Patrick Swayze played dancers auditioning for the Chippendales. Written by the legendary James Downey, the sketch features a half-naked Farley confidently showing off moves, completely unencumbered by his size—or by the fact that his competition is the guy from Dirty Dancing.

Today, the legacy of the skit is still up for debate. SNL writer Robert Smigel, for one, said in The Chris Farley Show that he thought that the judges’ earnest consideration of Farley as a sexy dancer prevents the bit from being exploitative. Chris Rock, on the other hand, disagrees. “I always hated it,” he said in the book. “The joke of it is basically, ‘We can’t hire you because you’re fat.’ I mean, he’s a fat guy, and you’re going to ask him to dance with no shirt on. OK. That’s enough. You’re gonna get that laugh. But when he stops dancing you have to turn it in his favor. There’s no turn there. There’s no comic twist to it. It’s just fucking mean.”

What’s not up for debate is the extent to which the Chippendales skit put Farley on the map. And while Farley struggled with body image issues, he was never afraid to play up his weight as a way to make audiences laugh.

Many of Farley’s funniest characters required the big man to throw his body around a room, but his outsized energy, not just his physical size, made him hysterical. In “Bill Swerski’s Super Fans,” he stole the show as a delusionally optimistic, mustached Bears diehard with a thick Chicago accent. “He had that physicality, that swag, that just put it over,” George Wendt, one of the fellow Super Fans, told me in 2018. “He could say anything, and then with his body language, it would just be hilarious. ‘How are ya, Bob?’ It’s not a joke at all unless it’s Farley.”

Farley brought Matt Foley to SNL, too; in the character’s first appearance on the show, as he yelled and adjusted his belt mere inches from their faces, host Christina Applegate, David Spade, and even the unflappable Phil Hartman could barely keep themselves from laughing. Still, nothing quite captured Farley’s self-deprecating charm like “The Chris Farley Show.” On the mock interview program, he nervously chatted with celebrities, smacking himself on the head and pulling his hair after asking dumb questions. His childlike tenderness was so strong that his guests, including Paul McCartney, would fall for him anyway.

At the outset of his tenure on SNL, Sandler’s value to the show wasn’t nearly as apparent as Farley’s—compared to his scene-stealing buddy, he was a subtle presence. But he had an approach that didn’t resemble what anyone else was doing in sketch comedy at the time, and a voice that was his, and his alone. “I thought that Sandler brought a really great breath of fresh air to the show and relaxed the show when it was getting kind of uptight and formulaic,” Odenkirk, a longtime writer on SNL, said in James Andrew Miller and Tom Shales’s Live From New York: The Complete, Uncensored History of Saturday Night Live. “So I liked what Adam did. But I think his fame or his success did surprise maybe everybody.”

As the faux-Italian Opera Man, Sandler displayed an impressive vocal range while singing about current events. With Canteen Boy and Cajun Man, he relied on a formula that served him well over the years: funny voice plus weird facial expression equals laughs. But what truly made Sandler a household name was his music. His holiday celebrations “The Thanksgiving Song” and, to an even greater extent, “The Hanukkah Song,” ended up getting airplay around the country. (During the holidays, radio stations still play them.) And for his performance of “Lunch Lady Land,” Farley dressed up as the title character and danced around the stage. In 1993, Sandler got his first taste of massive success, going platinum with his comedy album They’re All Gonna Laugh at You!, which featured several of his songs—and taught millions of kids how to curse creatively.

Within a few years of their debuts on SNL, Sandler and Farley had begun landing small parts in movies. The former popped up in Nora Ephron’s Mixed Nuts and the latter in Wayne’s World. They also both appeared in the SNL sketch adaptation Coneheads and the rock ’n’ roll hostage crisis flick Airheads. Neither got a shot at a starring role, though, until 1994, when Michaels expressed interest in Farley and Spade making a buddy comedy together. The two mismatched castmates had become close friends, and the SNL creator thought that their Odd Couple–like chemistry would translate to the big screen.

Bonnie and Terry Turner, who’d penned Wayne’s World, wrote the movie. Peter Segal, who had made Naked Gun 33⅓ and directed Farley in an episode of Tom Arnold’s sitcom The Jackie Thomas Show, remembers Paramount sending him the screenplay. Tailored for Farley, who was set to star as an immature recent college graduate unexpectedly forced to take over his father’s company, at the time the project was called Billy the Third: A Midwestern. “I thought he was the funniest man on the face of the earth and I dreamed of introducing him to a movie audience as a lead,” Segal says. “I thought he was ready, but the script was not ready. It was in bad shape.” (The Turners could not be reached for comment.)

Segal then met with Michaels, who advised him to tell the Turners what he thought of their work. “That was the wrong thing to say because I had so many notes,” he laughs. “I was new at movie-making, and there’s an art to giving notes. I just blasted away.” Needless to say, Segal didn’t get the job. But by that summer, after a handful of other directors turned down the gig, the studio reached out to him again. “They were losing the window,” he says. “David and Chris were gonna have to go back to SNL. And so they were desperate. And they called me back and said, ‘OK, what were your notes again?’”

With Segal hired, Michaels sent SNL writers James Downey and Fred Wolf to L.A. to help fix the script. Several days of pleasant lunch chats followed with zero work getting done. “Finally at the end of the week I said, ‘So, Jim, what about this script? What do we do?’” Segal says. “He said, ‘Oh, this is terrible. I can’t help you.’ And he went back to New York. And I’m like, ‘OK! Hey, Fred, I guess that’s that.’”

Segal says he quit the movie on a Friday. Two days later, his home phone rang. “It’s Sherry Lansing,” his wife said, her face turning pale. “She wants to talk to you.” Lansing, the Paramount chair who during a dispute with Mike Myers over the Wayne’s World 2 script infamously threatened to sue him and take his “fucking house,” wasn’t about to accept Segal’s resignation. “She said, ‘Pete, I have a team of lawyers speeding to the studio right now on a Sunday to figure out how to sue you for tens of millions of dollars and take your home from you unless you do this movie,’” he remembers. “And I said, ‘Have you seen my home? It’s really not that great. I don’t think you’d want it … but why are you forcing me to do this?’ She goes, ‘Oh, honey, I know you can do it.’”

“I believed in Chris Farley,” says Lansing, who calls Tommy Boy one of the funniest movies of all time. “I think he was a comic genius. And I believed Pete was the perfect director for it. If Pete had left, the whole project would’ve fallen apart.”

Segal then called Wolf, who agreed to help doctor the screenplay. “Fred was the hero on that movie,” Segal says. With little to go on, the two began collecting embarrassing personal experiences. Segal had recently misjudged the distance from a gas pump to his car; that went on an index card. Wolf told a story about the hood of his car flying up on the freeway; that went on an index card, too. Soon they had a pile of index cards, which was enough to cobble together a new draft—sort of. “What we had was 66 pages,” Segal says. “I said, ‘That’s half a script. I don’t even know how this movie ends.’ But I just had to start shooting.”

In September 1994, Segal began filming what would become Tommy Boy in Toronto. Not long before that, in the same city, another production starring an SNL star wrapped. It was called Billy Madison, and was a movie with an amusingly similar premise following a petulant, privileged protagonist—played by Adam Sandler—who jumps through a series of hoops (in Billy’s case, repeating all 12 grades of school) in order to become a worthy successor to his father. Herlihy and Sandler wrote Billy Madison’s screenplay in the hopes that Michaels would help get the movie made. “We wrote it in Microsoft Word using the tab key a lot,” Herlihy says. “That was my first script.” At the afterparty of Nicole Kidman’s appearance on SNL in November 1993, Herlihy remembers talking to Michaels about the script. “He was like, ‘Yeah, I don’t like it,’” says Herlihy. “And then he had some ideas. At that time, I had no idea that you make compromises and that it’s a collaborative medium. And I just thought, ‘I’m not doing any of those compromises.’ So it was kind of dead.”

To Herlihy’s surprise, the script was still very much alive, and one day, he started receiving faxes emblazoned with the Universal Pictures logo. It turned out that producer Robert Simonds, who’d made Airheads with Sandler, was interested in doing Billy Madison. The film’s budget was only $10 million, but that didn’t matter to Sandler: He finally had his own movie. “Billy’s the closest I’ve come to playing myself,” he told Entertainment Weekly in 1995. “I feel so much pressure because I want it to be as good as it can be. Dennis Miller told me that you only get famous once and then you are famous. But the best part is becoming famous. Right now I’m the underdog. It feels good.”

Like Tommy Boy, Billy Madison got off to a rough start. Universal fired director Stephen Kessler, a friend of Sandler’s, two weeks into filming. “The studio wanted a less stylized movie, more of me being a goof,” Sandler told EW. “It was very sad, like breaking up with a girlfriend. But he’s doing well.” At the time, Tamra Davis was coming off directing CB4, a hip-hop music parody cowritten by and starring Chris Rock. “I was living in that world,” says Davis, who married Mike D of the Beastie Boys in 1993. CB4 had made Universal nearly $18 million against a budget of $6 million, a respectable return. And so, in a pinch on Billy Madison, the studio turned to her again. As a then-32-year-old woman, she realized that she wasn’t part of the movie’s target audience. “Like, I’m your worst demographic,” she says, though she also makes sure to note: “I also laugh like I’m a 12-year-old boy.”

For a while, the creators of Farley’s first film couldn’t even agree on a title. Billy the Third: Midwestern was scrapped in the middle of production because the main character’s name was too similar to Billy Madison, a film that Michaels wasn’t producing. To avoid any confusion, Billy the Third became Tommy Callahan III. As for titles, XL and Fat Chance were discussed as alternatives, before Michaels suggested Tommy Boy. “We were like, ‘What?’” Segal remembers. “At first I hated it. And I’ve learned that’s what happens when you change a title. No one will be satisfied.”

Not locking down title right away is one thing, but not having a finished script? Holy shnikies. Shockingly, though, Paramount wasn’t too concerned. “It was such an inversion of what’s going on these days, which is, the studio wanted that slot filled with that comedy no matter where the script was,” says Wolf. “They said, ‘Yeah, get the script to what makes you guys happy. We just want that movie.’”

On set, Segal remembers realizing that his nervous lead actor saw him more as a coach than a director. “There were times when he would get so amped up on caffeine because he was clean and sober in Tommy,” Segal says. “He replaced drugs and alcohol with caffeine and cigarettes. Sometimes I would tell him, ‘Jog around.’ When we were shooting at the college, I said, ‘Hey, take a lap around the courtyard. Come back. Calm down, you’re freaking out.’ He would get really mad at himself for not being able to nail a take.” A few times, Segal asked Farley to drop and give him 20. After doing the push-ups, he’d rush back and ask what Segal wanted him to do next.

Thankfully for the director, Farley and Spade’s relationship was an endless well of material. Segal and Wolf would simply watch the duo’s interactions and then drop the exchanges they witnessed into the script. “One day there was a wardrobe test, and Chris came out in his now iconic brown tweed jacket, and he said to David, ‘Hey, Dave, does this suit make me look fat?’” Segal says. “And Dave said, ‘No, your face does.’ And I said, ‘Whoa whoa whoa, that’s gold.’”

In another scene, Tommy slips on Richard’s teeny blazer and sings, “Fat guy in a little coat” before accidentally ripping the jacket in half. Farley used to do something similar in the SNL offices. Originally, he was filmed saying the line, not singing it. But after looking at the dailies one night, editor Bill Kerr heard Farley off-camera, mindlessly humming the line. The next day Segal went back and reshot the sequence. “Again,” he says, “that was just observing them and finding the gold.”

For a short stretch that summer, the cast and crews of Tommy Boy and Billy Madison were in Toronto together. “We had the wildest time on the planet, I think, every night,” Davis says. “It was like a dorm room. We saw skits that they did at night that would end up on Saturday Night Live the next season.”

But while they may have been going wild, the creators of Billy Madison took their jobs seriously. “We weren’t back in the trailer at craft service having coffee,” Herlihy says. “We were there for every shot and every take. We must’ve drove Tamra crazy.” Herlihy and Sandler practically tormented Darren McGavin, who plays Billy’s father, about his line reads. “We’d make him say it exactly the way it was in the script,” Herlihy says. “And just make him do it over and over and over again.” And while Davis may not have always understood Sandler and Herlihy’s comedy—Billy’s flirting with his housekeeper Juanita, who’s played by Broadway great Theresa Merritt, baffled her—she trusted them to come up with the funniest possible material. “I would just encourage the humor and push it to see how far you could go,” Davis says, “until he does actually make me laugh.”

While both Tommy Boy and Billy Madison are about sons attempting to honor their fathers’ legacies, the latter is far more absurdist. Billy drunkenly hallucinates a penguin, leaves a flaming bag of dog poop on an old man’s doorstep, and freaks out on his third-grade classmates when his teacher calls him out for his inability to write cursive z’s. Oh, and Farley shows up—as a bizarrely angry school bus driver, he steals every scene he’s in (and literally steals 30 bagged lunches). At one point, within seconds of his character getting angry, he makes his face turn almost purple. “How could a human being just by force of will change their hue from sort of this pale white to this bright red?” Herlihy says. “It was remarkable. The engine that was going inside him to make his body do those things, it was incredible.”

In early 1995, Billy Madison (February 10) and Tommy Boy (March 31) hit theaters. Most critics, unsurprisingly, despised them. Gene Siskel wrote that Sandler’s film was “the latest entry in the American cinema’s investigation of dumb-and-dumber heroes.” Roger Ebert’s assessment of Farley’s comedy, meanwhile: “The movie is an assembly of clichés and obligatory scenes from dozens of other movies, all are better.”

But despite poor reviews, both opened at no. 1 and became minor hits. Billy Madison grossed $26.5 million and Tommy Boy pulled in $32.7 million. In a post–Wayne’s World world, Sandler and Farley showed that maybe SNL cast members other than Mike Myers did have movie star potential. Their modest success also proved that in the wake of Jim Carrey’s rise and whatever it was that Pauly Shore was doing, there remained an appetite for gleefully adolescent humor. After all, the country’s middle-schoolers weren’t ready for the spate of more sophisticated, sometimes R-rated teen movies about to arrive. But they loved Sandler and Farley.

After Billy Madison and Tommy Boy, Sandler and Farley should’ve returned to Saturday Night Live as conquering heroes. Instead, they found themselves portrayed as symptoms of a show in shambles. Ratings had dipped, and the sophomoric Bad Boys of SNL, of which the two buddies were a part, had led to a critical backlash. Whatever magic the two comedians had found on the big screen—in movies that perhaps skewed toward a younger demographic that wasn’t tuning in to late-night television every Saturday—was no longer translating to the adult-focused SNL. The March 13, 1995, cover of New York magazine featured a photograph of Farley with the shell of an old TV set on his head. The accompanying headline was, “The Inside Story of the Decline and Fall of Saturday Night Live.”

Later that year, Michaels fired Sandler and Farley. Surely a blow, it at least allowed them to fully transition to movies. Sandler made Happy Gilmore, about a hockey-playing “blue-collar moron” who becomes a professional golfer. Farley, meanwhile, appeared to have even more options than his pal—he was in talks to star in The Cable Guy and Kingpin—but Paramount, which had signed him to a two-picture contract, nixed those opportunities. Instead, the studio quickly slotted him into Black Sheep. Written by Wolf and directed by Penelope Spheeris, it wasn’t a sequel to Tommy Boy, but with Farley playing the goofball brother of a gubernatorial candidate opposite David Spade’s straightlaced campaign staffer, it certainly felt like a rehash.

Within two weeks in February 1996, Black Sheep and Happy Gilmore came out. Each cleared $30 million in theaters. And then, all of a sudden, Sandler became comedy’s box office king. “You look back on it now and it seems like it’s, ‘Bam, bam, bam,’” says Herlihy, who’s written 11 of Sandler’s movies. “In real time, it was in such slow motion.” His two movies in 1998, rom-com The Wedding Singer and underdog football flick The Waterboy, combined to make $309.3 million. The next year, he starred in Big Daddy, which raked in $234.8 million. While Sandler’s sense of humor never radically evolved—he’s still making versions of the movies that he made in the ’90s—he managed to adapt his shtick so that it fit in broader, more heartfelt comedies. He grew up, but not enough to alienate his core audience. “He started out with Billy Madison and Happy Gilmore and that’s what really what put him on the map,” says Peter Segal, who directed Sandler in a string of early-2000s hits: Anger Management, 50 First Dates, and The Longest Yard. “And then he matured and became a man in these roles.”

In a just world, Farley would’ve been right there with his friend. But unlike Sandler, he was never able to find subsequent projects that truly showcased his talents. He did discuss playing Fatty Arbuckle—the silent film star who was wrongfully accused of rape and manslaughter in the early 1920s, and with whom Farley felt a deep connection—in a biopic, and he also recorded a pathos-filled vocal track for Shrek. “Rossio and Elliott, who wrote Shrek, told me that they patterned Shrek and Donkey after Farley and Spade in Tommy Boy,” Segal says. “That’s the prototype. That’s why they wanted Chris.” But neither film panned out for him. Instead, Farley made the silly Beverly Hills Ninja, which tapped into his physical comedy but failed to burst the “fatty falls down” bubble in which he’d always been confined.

On December 18, 1997, after years of addiction and dozens of rehab stints, Chris Farley died of a drug overdose at his home in Chicago at the age of 33. Since his death, there have been many tributes to the comedian, though most can be distilled to how Segal (and Sandler’s SNL tribute) describes him: “There was nobody funnier on the planet.”

For many aspiring comedic actors growing up in the ’90s, Adam Sandler’s career and approach was the mold. “He’s the best example of someone you looked up to when you were young,” Jonah Hill affirms. But Chris Farley was different. What he had was impossible to replicate—and, twistedly, tragically, impossible to truly capture on film.

Once, while walking through Studio 8H, Wolf ran into a brand-new Saturday Night Live cast member. “I’m like, ‘Hey, man, what’s going on?’” the writer recalls. “And he’s like, ‘Oh, I’m just watching Farley out there. Look at him.’” Farley, who after leaving the show had returned to the set to visit, was out on the monologue mark doing pratfalls for the veteran crew. “I don’t have that. He’s like a hurricane.” That SNL novice? His name was Will Ferrell.

This piece was updated on September 11 with additional information after publication.