‘Cha Cha Real Smooth’ Director Cooper Raiff Is Your Typical 20-Something… With a $15 Million Movie Deal

Cooper Raiff has been embracing a nomadic lifestyle, crashing with friends in Los Angeles and traveling to national parks while he’s in between jobs. But the lack of a permanent residence does have its drawbacks. He moved into a new sublet in Queens — where he’s preparing to shoot a movie — late last week and opened the door to a disaster zone, the kind of mess that compels one to immediately wash the bed sheets.

“If I’m going to be put up by this movie for a year, I don’t want to pay for something during that,” he says, noting that producers of his upcoming film will soon supply housing. “That’s not smart.”

The temporary living situation is not an atypical experience for a 25-year-old living in New York City, save for the fact that the move coincided with the release of Raiff’s second feature film, “Cha Cha Real Smooth,” which won the audience award at Sundance and sold to Apple for $15 million, in one of the biggest deals in the festival’s history. Now, six months after charming the dancing shoes off virtual festival-goers, the sweet coming-of-age story has just opened in select theaters and on Apple TV+.

“I felt ready for it to be out in the world. But today feels overwhelming,” he admits just hours after his labor of love had premiered. “I’ve been getting so many texts and emails. I decided I’m not going to look at Instagram or Twitter or search ‘Cha Cha’ on Google. I have to figure out the way I want to handle being inundated with reactions.”

Raiff, wearing a plain white tee with a cardigan tied around his waist, is nursing a hot cup of joe and staring down a half-eaten bagel at a breakfast spot in Queens. But there isn’t enough coffee in the world to jolt the filmmaker out of his stupor. There’s a reason — he admits at a glacial pace — that he’s speaking at a cadence so unhurried, with the words tumbling out of his mouth so leisurely, it may as well be in slow-motion.

“Do you know what Unisom is?” he asks, referring to the natural sleep aid. “I’m hungover from that.”

Usually, he explains, he only needs half a tablet to knock him out. But this was the night before his film would be available to the widest audience yet, and he couldn’t rely on ordinary measures to fall asleep. Popping a partial Unisom pill wouldn’t do — not today.

“I took a full one. It obliterated me,” Raiff says. “I usually have dreams. But take a full Unisom,” he warns, “And you’ll literally die and then wake up.”

Raiff has felt like he’s been in an altered state of reality since “Shithouse,” a micro-budget film he made in college, won the grand jury prize at SXSW in 2020. He’s been on Hollywood’s radar ever since by cultivating a do-everything-yourself approach to independent filmmaking, which calls on Raiff to not only star in his movies as the shaggy romantic lead but to write, produce and direct them as well.

Despite the festival accolades, Raiff’s first feature went relatively under the radar, at least to the general public. Or, as he jokes rather bluntly, “No one saw ‘Shithouse.'” So there’s a greater sense of pressure with “Cha Cha Real Smooth,” which co-stars Dakota Johnson and Leslie Mann, and is backed by the biggest company in the world.

That’s only amplified Raiff’s dream-like state, which ramped up after Apple, having newly steered Sundance darling “CODA” to a best picture Oscar, wrote an eye-popping check to buy “Cha Cha Real Smooth.” It reached its zenith after his parents sent a video of Jimmy Fallon introducing a clip from the movie on “The Tonight Show.”

“You know in movies, sometimes Jimmy Fallon will be in the movie [as the host of ‘The Tonight Show’], and it feels fake? It felt like that. So utterly fake,” Raiff says. “When Jimmy Fallon said, ‘Here’s a clip from ‘Cha Cha Real Smooth,’’ I didn’t know how to process it.”

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Raiff did not expect to become a director. But hey, who else is going to shoot your first movie for free?

With a calling to write and act, Raiff made a scrappy, roughly 50-minute version of “Shithouse” as a sophomore at Occidental College in Los Angeles. As the story goes, a daring Raiff sent the student film to indie director Jay Duplass, who not only watched the movie, but took the youngster under his wing and offered a crash course in film festivals and distribution.

At the urging of Duplass (whose credits include “The Puffy Chair,” “Jeff, Who Lives at Home,”  HBO’s “Togetherness”), Raiff turned “Shithouse” into a feature-length film and tried his luck at SXSW (which went virtual that year due to the pandemic), where the movie could attract buyers.

“I was like, ‘Right… someone has to buy it. You don’t just put it on YouTube,'” Raiff recalls.

During his third year as a media arts and culture major, he left school to pursue filmmaking full time. “I convinced my parents that Jay thought I should drop out,” he says. “That was kind of a lie.”

That gamble turned out OK for Raiff. After winning the festival’s top prize, he took a lot of (mostly pointless) general meetings until he met Ro Donnelly, who ended up producing “Cha Cha Real Smooth” with Johnson.

“I look for purity of vision and collaborative energy in a filmmaker,” says Donnelly, who co-founded TeaTime Productions. “He had such a distinct voice.”

He pitched to them an idea that developed into a charming tale about an aimless college grad named Andrew (Raiff), who moves back to his parent’s house in New Jersey and becomes a bar mitzvah party starter. On the dance floor, he strikes up a friendship with Domino (Johnson), a 30-something mother to an autistic child (portrayed by Vanessa Burghardt).

Raiff believes part of the appeal is that there aren’t any unexpected deaths or tragic twists to drive the plot; it’s mostly about good people trying to be good while struggling with everyday issues. “It’s a small movie about small things,” he says.

Raiff drew inspiration from his own life; his younger sister is disabled and can’t walk or talk. “It really rocked my parents,” he says. “From then on, I felt like my job in life was to provide relief.”

In “Cha Cha Real Smooth” and “Shithouse,” in which Raiff plays a friendless college freshman, he’s crafted refreshingly sensitive characters who feel comfortable openly shedding tears and talking about feelings. They’re the kind of 20-something guys you’d be hard pressed to find on Hinge.

“I cry a lot,” Raiff says of his reality. “I’m not trying to start a revolution.”

He may be in touch with his emotions, but he doesn’t pretend to have it all figured out. “Just because I made a movie doesn’t mean I know who I am,” he says. With that realization, he’s started going to therapy for the first time.

“It’s nice to have someone objective to look at your life,” he says. “My mom is a psychologist, so I have coasted on thinking, ‘I can look inward.’ But I’ve been scared to get that objective listener.”

It’s an undoubtedly interesting period for Raiff, who effectively skipped the struggling indie filmmaker phase that people usually endure in their early 20s. But despite two crowd-pleasing features on his resume, Raiff still finds himself punching up against his age.

“I’m a young person who doesn’t know much at all. That means when people don’t take what I’m doing at all seriously, I have to be like ‘Yeah, I understand.’”

His relative youth is betrayed at times by his influences. The 2007 fantasy drama “Bridge to Terabithia” inspired a love of movies and Sofia Coppola’s 2003 romantic dramedy “Lost in Translation” made him want to become a writer.

Despite a deep admiration for Josh Hutcherson’s acting abilities, Raiff had other career ambitions. Growing up in Dallas, Raiff developed a love for playing basketball. “And then everyone hit puberty,” he groans. “I was like, ‘Oh, that stinks.’ Everyone got very strong and fast and tall.” Around the same time, Raiff was in the thick of bar mitzvah season.

He went to a small school, which by his estimation had a large Jewish population. As a result, he attended many a simchas as a seventh grader. Though he’s not Jewish and therefore did not have a bar mitzvah, they became formative events for him. “I had my first kiss at a bar mitzvah,” he says.

Given the setting of “Cha Cha Real Smooth,” people have often mistaken Raiff as being Jewish. Ironically, he says, “A lot of that period was defined by that outsider perspective that looked inside this very tight knit, loving, family-oriented [religion] that loves traditions.”

In high school, his longtime girlfriend was Jewish, and, he recalls, “I went to every Shabbat dinner and desperately wished I knew the prayers. Her parents looked at me like, ‘You’re not going to marry our daughter.’”

•  •  •

Raiff has already lined up his next movie, “Trashers,” a father-and-son drama that takes place in the world of hockey. Though the cameras haven’t started rolling, he’s been meeting with studios and distributors in the hopes that he doesn’t have to wow buyers at Sundance or SXSW.

“I don’t want to do the festival route with ‘Trashers,’” he says. “It’s a working-class, blue-collar movie. Thinking about playing it at Sundance and a bunch of people from Los Feliz coming to watch it… it’s going to miss its potential there.”

For the first time, he’s relieved to say, Raiff won’t be acting in something he’s directing. “I trust myself as a director now,” he says. “I can figure it out without having to be in the middle of a scene.”

Building on that confidence, Raiff wants to remain selective in the projects he takes on — lest he become the kind of filmmaker who says yes to anything and everything in the name of a sweet paycheck. “I want everything I do to always be execution-based and not a foreign sales payday.”

He’s OK if those limitations mean he never makes another film. There’s only one goal he’s really chasing: “I really want my grandma to love a movie I make. And she really did not like ‘Shithouse,’” he says with a laugh. “She was like, ‘Lots of talking.’”