It’s easy to conflate the real Cooper Raiff with the youthful, hopeful, emotionally wobbly characters he creates for himself. The 25-year-old has written, directed and starred in two independent movies, 2020’s Shithouse (worth a watch despite the title!) and the newly released Cha Cha Real Smooth, and they’re both quite good—so sweet and engaging, in fact, that they may have encouraged those who’ve panned them to interpret the doe-eyed solipsism of the characters Raiff plays as his own self-regard.
It’s harder to make that assumption in person: Raiff is both softer-spoken and more serious than, say, Andrew, the guy in Cha Cha Real Smooth who graduates college and gets an unofficial job as a party-starter for local bar mitzvahs. (Andrew is not Jewish, and neither is Raiff.) As we talk in a coffee shop in Ridgewood, Queens, he can be unnervingly direct, maintaining his eye contact and confidence, leaning forward in his seat. He’s neither as gregarious as Andrew nor as hesitant as Alex, the lonely freshman from Shithouse. (About those titles: “I want to make a movie that when the title card comes up at the end, you’re like, ‘I actually do love that title.’” Still, he admits, “going to a theater and saying, ‘two tickets for Cha Cha Real Smooth,’ at first it’s like, fuck off.” )
Yet these characters obviously do spring from his own experiences. Shithouse is especially attuned to an emotional reality of college not often depicted. “Movies about college are written about 50-year-olds who are like, what a great playground,” Raiff notes. He wanted to explore a different idea: “the pain of leaving home and growing up.”
Raiff cites the 2007 film version of the young-adult novel Bridge to Terabithia as sparking his youthful interest in filmmaking, along with the work of Sofia Coppola, especially Lost in Translation, whose clear authorial voice drew him into the idea of writing movies: “She’s saying something very specific, and the way that she’s saying it is so funny, and unassuming, but so poignant.”
He traces invisible maps on the table while making his point. It’s a casual gesture, but it seems appropriate: Raiff was mapping out character ideas for what became Cha Cha Real Smooth for a few years before actually writing the full screenplay. Andrew, the earnest 22-year-old without a lot of boundaries, intersects with Domino (Dakota Johnson) and her autistic daughter Lola (Vanessa Burghardt), who are based somewhat on the bond one of Raiff’s sisters, who is disabled, shares with their mom. Andrew, like the homesick Alex in Shithouse, also has a close relationship with his own mom, played by Leslie Mann; the movie is a whole New Jersey ecosystem of parent-child bonds, mom-friends, next-gen siblings, and high school acquaintances, sketched with affectionate detail. I tell him I love the mother-son relationships in his movies, how tenderly he depicts family connections that broader comedies might use as joke fodder, and ask about what his relationship with his mom is like. “I think I definitely am a mama’s boy, but I do take it seriously, I guess?” he says.
Raiff fondly remembers going to the Angelika Dallas often with his mother. His dad is less of a movie guy. (The only film Raiff is certain his dad really likes is Francis Ford Coppola’s The Outsiders.) Their connection was over something else entirely: “I thought I was going to be in the NBA up until seventh grade, and then everyone hit puberty. But I still played in high school, and my whole bond with my dad was basketball. He went to every single game, and my last high school game was the most devastated we’d ever been together. It was like, what’s our bond going to be, how are you going to show me love, if there’s no basketball game to show up for?”
That dynamic will inform his next project, Trashers, about a mob-connected father, played by David Harbour, who buys a minor-league ice hockey team for his teenage son. It’s safe to assume that Raiff, having clearly progressed from freshman to recent graduate in his own movies, will probably not play the eighteen-year-old son. But as the unequivocal lead in both of his movies so far; would he act for other filmmakers? “I’m really not good at saying other people’s words,” he says. “I’m just not a very good actor in that way. But I love so many directors, and if a director did say something like, do you want to play a small role in this, I think I’d love to find a way to be on a set without being like ‘hey, can I come be on your set?’ That feels like an organic way to do that.”
In the meantime, he’s trying to take some cues from his characters, though maybe not in the way you might expect. “Andrew hates being alone and figuring out who he is as a person. He doesn’t have any ground to stand on, it’s very unhealthy,” he says about the kind but ultimately somewhat misguided devotion his character in Cha Cha shows toward an older woman and her child. “I think I do the same thing with relationships, and I think I do the same thing with making movies. So I’ve tried to take some of my advice, and take a moment.”
To that end, the conversation turns to music he’s been listening to lately, and he mentions Waxahatchee, the indie-rock vehicle for singer-songwriter Katie Crutchfield. It turns out we went to the same New York tour date last fall. “I loved the whole concert, and then she played at the very end, a song that was all about death,’ he says. “That song came on, and I wasn’t on drugs, and I only had like two beers, feeling totally fine, and all of a sudden I had this panic attack about the song. I almost passed out. But it was the best time ever until that moment.”
Does he think about death a lot? “I try not to, because I don’t think life is about death. There’s this song by Bill Callahan, where he’s like, ‘it’s time to put God away.’ It sounds really dark, but I think about it as like, let’s put this away, that’s not what life is about. I read a lot of Camus in college, and he’s like, always think about death, because that’s the only way that life is lived to the fullest, and for a second, idiotically as a 20-year-old, I was like, OK! But it sent me into a lot of spirals.” This is the type of sensibility that helps make movies made by an impossibly youthful writer-director actually resonate. Raiff puts it another way: “I try to get at a joyful sadness.”