Cooper Raiff is still figuring some things out. The Dallas-born writer, director, and actor is currently making the rounds with his second film, Cha Cha Real Smooth, which debuted this past January at the Sundance Film Festival, where it won widespread praise, picked up the Audience Award, and sold to Apple for $15 million. Apple’s last high-profile Sundance pickup went on to win Best Picture, so it seems likely that good things await Cha Cha Real Smooth, which debuted in limited release and on Apple TV+ on June 17. Raiff recently turned 25. All signs suggest he’s on the right path. But Raiff’s not so sure.
In Cha Cha Real Smooth—its title taken from the song you’ve definitely heard at a birthday party—he plays Andrew, a directionless recent college grad who moves back in with his family. Chronologically it’s a natural successor to Raiff’s first feature, Shithouse, the story of a college freshman named Alex (also played by Raiff) who feels lost and alone after moving away from his family. (An ability to choose titles that stick in the mind unites his two features.) Raiff was in his early 20s when he made Shithouse, a film with a protagonist in his late teens. He was in his mid-20s when he made Cha Cha, a film about a protagonist in his early 20s. When asked whether he’s especially comfortable making movies about phases of life he’s just left behind he replies without hesitation. “I love it,” he says during an interview at a hotel across the street from Wrigley Field. “I don’t feel like a great writer, so it feels like what’s special is that I haven’t shed that time, the person that I was. I can still touch those relationships and feelings that haven’t even resolved yet. Cha Cha is about a person ultimately realizing that his 20s are for him to figure out who he is.” Then he adds, “I haven’t figured out what my 20s are.”
When I point out that, having become a professional filmmaker he’s at least got that much figured out, his reply is less expansive. “Yes.” And then after a pause, “Sure.”
But even if it’s youthful confusion and trepidation that drive him, Raiff’s made those feelings work. He captures them well in Cha Cha, whose protagonist stares into a future that’s terrifyingly wide open—and ill-defined—after moving back in with his mother (Leslie Mann), middle school–aged brother David (Evan Assante), and stepfather (Brad Garrett). Unsure what to do beyond making vague plans to join his college girlfriend in Barcelona (even though she seems, at best, lukewarm to the idea), Andrew takes a day job at a fast food restaurant while working nights as a party starter on the bar and bat mitzvah circuit. As the summer unfolds, he drifts into a nebulous friendship with Domino (Dakota Johnson), the single (but engaged) mother of an autistic teen named Lola with whom Andrew shares an easy rapport (Vanessa Burghardt, playing a character inspired by autistic friends of Raiff’s disabled sister).
The film, in many respects, covers familiar ground. There’s a tradition of movies about men on the cusp of adulthood drifting through their childhood hometowns that runs from The Graduate through Garden State, but Raiff’s earnest, uncalculated approach sets this movie apart. So does the generosity of his film’s spirit. Andrew’s on a journey of self-discovery, but it’s one that includes recognizing that those around him are on journeys of their own that may only intersect with his momentarily before diverging. It’s a film without villains—even the bullies who pick on Lola might grow out of it.
That sense of generosity extends to the way he talks about his collaborators. Raiff’s quick to praise Johnson and her producing partner Ro Donnelly, who together run TeaTime Pictures, and talks about working with Johnson to shape her character over the course of a five-month collaboration. “I wanted to make a movie that kind of highlighted all of her chops,” Raiff says. “I think she responded to that, and she was of course going to be a part of the creation of that character, because my pitch to her was creating a character with her.” He’s just as effusive about others, noting that Mann is his mother’s favorite actress and lauding Burghardt (who, like her character, is on the autism spectrum), Assante, and costar Colton Osorio for their work ethic. “They were the ones, outside of Dakota, who wanted to work all the time,” he says. “They always wanted to get on a Zoom with me.”
Though Cha Cha Real Smooth is set in New Jersey, Raiff drew on his experiences attending bar and bat mitzvahs in Dallas and his memories of a community he knew well, if from a slight distance. In Dallas he attended a school that was “40 percent Jewish” and his friends’ coming-of-age celebrations became central to his social life. “I was going to a service and a party every single Saturday,” Raiff recalls. “Seventh grade is already such a visceral time. And then: puberty, and kissing, and spin the bottle, and horrible BO. That’s the thing I remember the most about bar mitzvahs.” Such events’ importance went beyond partygoing, however. “The Jewish community is so tight-knit,” he continues. “My girlfriend in high school I dated for three years, I did Shabbat dinner every Friday with her. That defined a lot of my childhood—that outsider perspective. Not saying prayers with them, but feeling like, ‘God, this community is ... I feel jealous.’”
Raiff took acting classes in high school and recalls being “obsessed” with watching movies, by which he mostly means the Andrew Garfield Spider-Man films. But where Dallas serves as the backdrop to one half of Raiff’s origin story, the Los Angeles neighborhood of Eagle Rock, home to Occidental College, provides the other. “I never wanted to be a director until I wrote something, and tried to get so many people to direct it, and then realized no one wanted to direct my college love story,” Raiff says. “So I had to do it.” That college love story became Madeline & Cooper, an almost hour-long short costarring Raiff and his college girlfriend, shot on campus over spring break. Confident he had something worth sharing, Raiff uploaded it and tweeted “Bet you won’t click on this YouTube link” to indie filmmaker Jay Duplass, who lived near campus. “I created a Twitter account just for this,” Raiff told Occidental’s website last year. “I had zero followers and I followed one person—and it was Jay.”
Duplass proved to be a well-chosen target. The writer, actor, and director watched the film and saw enough promise in it to meet with Raiff and offer advice on how to turn the short into the full-length feature that would eventually become Shithouse, in which Raiff would costar opposite Dylan Gelula (Unbreakable Kimmy Schmidt). But for Raiff, committing to the film meant dropping out of school to pursue directing full time, without telling his family or new mentor and with no promise it would all work out. “We didn’t have any money,” he recalls of the experience. “People were not getting paid. And I think people didn’t have faith in the process.”
In the end, it did work out, but only after considerable risk-taking and a grueling, low-budget production and no promise of finding a place in an already overcrowded marketplace. (Maybe those goofy titles aren’t such a bad idea after all.) Shithouse charmed audiences at the 2020 SXSW Film Festival, won the Grand Jury Prize for Best Narrative Feature, and secured distribution and a small theatrical run with IFC Films. Heartfelt and determinedly modest (and much less crude than its title would suggest), Shithouse bears the influence of the Duplass brothers and their mumblecore peers, but also fellow Texan Richard Linklater, with its focus on two people taking their first steps toward becoming a couple over the course of a night filled with walking and talking. Still, like Cha Cha, the film wears its influences lightly. Both play like the work of a filmmaker interested in drawing on the past without imitating it, or squeezing his stories into shapes deemed successful by screenwriting guides. “If someone told me the three acts of Shithouse, or the three acts of Cha Cha, or asked when they break off,” Raiff says, “I would be like, ‘Ah … I don’t know.’”
Shithouse also established Raiff as a charming screen presence, skilled at playing sensitive men comfortable talking about their feelings, a zone most other young actors don’t seem all that eager to explore. “I don’t know how not to sometimes,” he says. “My mom, like, cries every day, and so it’s hard to make a movie where people are not crying.” Raiff cries convincingly in both his films, plays well against both Johnson and the younger cast members of Cha Cha Real Smooth (particularly Burghardt), and brings an awkwardly comic touch to scenes like a job interview that goes horribly wrong. So it’s kind of shocking when he casually mentions that he doesn’t know whether he’ll ever act again, between noting that he begins thinking of films as a writer and that “directing is the thing that I really, really love so much and want to continue to work on and get better at.”
That might be one way in which Raiff is still figuring out his 20s. But, even if he walks away from acting, he won’t want for work. Next he’ll direct The Trashers, starring David Harbour in a fact-based story of crime, nepotism, and minor league hockey. On the horizon is Exciting Times, an Amazon series starring Phoebe Dynevor, which he’s slated to cowrite and direct.
It’s hard not to get a little worried when a young filmmaker who excels working on a relatively handmade scale has to find a place in Hollywood machinery increasingly oriented toward blockbusters and directors who can fill in the gaps between prefabricated action scenes. Other Sundance success stories have gone on to helm Fast & Furious and Marvel movies. When everyone from Chloé Zhao to Sam Raimi now squeeze their distinctive approaches into films dominated by a franchise’s house style, it often seems like scaling up is the only choice available. It’s not that these movies can’t be good, but swelling budgets often correlate with diminished risks and personal notes.
“I’ve been constantly talking about how I want to make sure that we’re not getting too big here,” Raiff says. “After Trashers, I know I’ll be going smaller than Cha Cha. Because I realized that I love this certain sweet spot that is lucrative. Like, why not do that?”
Maybe he has some things figured out after all.
Keith Phipps is a writer and editor specializing in film and TV. Formerly: Uproxx, The Dissolve, and The A.V. Club.