LOS ANGELES – For a while, working behind the camera didn’t suit Cooper Raiff very much.
“I never wanted to be a director,” he said. “When someone says they want to direct, I’m like, ‘Who do you think you are?’”
But at 25, the actor, writer and, despite his former sentiments, director, has made two bittersweet personal traits that have attracted critical and industry attention.
“I didn’t like the idea of directing because directors really need to bring everyone together and gain trust among the team and that’s not my comfort zone,” he said. “But I’m really good at making sure people want to be around me. I think it’s about me not wanting to be alone.”
Now Raiff has made a film that people seem to want to spend time with and where he confirmed his calling. His second work, “Cha Cha Real Smooth,” won the Audience Award at the 2022 Sundance Film Festival and was purchased for $15 million by Apple. That company led an earlier Sundance acquisition, “CODA,” to an Oscar for best picture earlier this year.
A coming-of-age comedic drama, “Cha Cha Real Smooth” (in theaters and on Apple TV+) centers on Andrew (Raiff), a college graduate employed as a bar mitzvah party starter and embroiled in a friendship of flirts with Domino (Dakota Johnson), a 30-something mother of an autistic teenager.
Sporting a dark green hoodie during a recent interview at a restaurant in the Westwood area of this city – casual attire in contrast to the establishment’s sophisticated ambience – Raiff exuded the same charming melancholy that permeates his work.
As he repeatedly ran his hands through his hair, the young storyteller spoke with an eager eagerness to sidestep small talk in favor of vulnerability.
“If you asked me, ‘Where will you be when you’re 25?’ I think I would have said, ‘I hope I’m happy and doing what I want to do,'” Raiff said, adding, “There have been times this year when I’ve been terribly unhappy with certain things in my life. . The two movies I made were objectively successful because we made money from them, but being successful doesn’t help with my dad issues. It doesn’t get me through the day.”
Before reluctantly finding himself calling the shots, the Dallas native spent much of his teenage years at a local acting studio. At that time, he hoped that acting would become his main mode of involvement with film.
Writing only came into his grasp when he was in his senior year of high school when a new drama teacher, Catherine Hopkins, encouraged him to do so, providing suggestions and feedback until he finished and put on his first school play with her help. .
“Bless her soul, she’s read some of the worst things ever,” Raiff said. “But she really helped me become a writer.” Hopkins, he recalled, had kind words to say about her film debut, but he believes she secretly wants her former student to be a playwright.
Eager to break into the industry, Raiff moved to Los Angeles to attend Occidental College. Still set on an acting career, he attended castings regularly until an audition for a UCLA short film, which required a stereotypical Texas accent, broke him. “That’s when I said, ‘I can’t do this anymore. It’s not good for my morale,’” he recalled.
Raiff then returned to writing. He put together an entire season of an episodic series, which he still wants to do someday, and sent it to every agent whose emails he could find online. Not surprisingly, his unsolicited submission didn’t get any traction.
“I realized that no one was going to read my stuff. That’s when, in my sophomore year of college over spring break, I made this bad movie thinking people were more likely to watch something than read something,” he explained.
This amateur endeavor, titled “Madeline and Cooper,” with him and his girlfriend as the leads and filmed with equipment borrowed from the university, followed the everyday mishaps of a college freshman. A fan of the “Togetherness” TV series, Raiff tweeted to his co-creator, Jay Duplass, and challenged him to watch his student project on YouTube.
“I said, ‘I bet you’re not going to click this link and then email me.’ He emailed me saying he won the bet and then we had lunch,” Raiff said. “I was at such a low point when I tweeted him because I had shown the movie to my parents, and they really didn’t like it.”
Duplass saw potential. “Within a few minutes, I realized that his sensitivity to filmmaking was very natural,” Duplass said in a telephone interview. “There was an emotional maturity to it, which I think is really what characterizes Cooper’s work more than anything.”
Over the next nine months, the two met regularly, as mentor and mentee, to perfect the screenplay for Raiff’s “Madeline and Cooper” as part of an informal crash course in independent and budget filmmaking. As the project took shape, Raiff introduced nearly a dozen directors to take over, but eventually had to take the role. That would mean not finishing college.
“I lied to my parents and said, ‘Jay thinks it’s okay for me to give up.’ That wasn’t true, but I was betting on us eventually making the movie. And we did, but Dad wasn’t happy.”
The resulting film, “Shithouse,” a professionally made version of his original student film, won the grand jury prize at the South by Southwest Film Festival in 2020 and was sold to IFC Films. Given how cheaply it was accomplished, Raiff earned a substantial amount of money, enough for his father to see his way as financially viable.
For “Cha Cha Real Smooth,” Raiff was against the idea of acting in his own movie again. But her TeaTime Pictures producers Dakota Johnson and Ro Donnelly were sure that no one else was better suited for the role. “He wrote Andrew for himself,” Johnson said over the phone. “So I wanted someone else to play him, which really can’t happen.”
Unbeknownst to the production team, Raiff hadn’t written a single page when they first met. He sold them on the concept of a lovable young man adrift who excels at livening up other people’s parties but has no idea how to start his own life.
“Cooper is incredibly observant. He notices little details that no one else does about someone’s personality or body language,” Johnson said of what led her to co-produce the film and co-star with Raiff. “I think that’s a really valuable feature when someone is making a movie.”
Shortly after the film’s world premiere in January, it was announced that Apple had secured worldwide distribution rights. “Cooper captured our imagination at Sundance with his screenplay about the beauty of relationships in all its forms,” Matt Dentler, Apple Original Films’ head of resources, said in an email.
Both of Raiff’s feature-length screenplays so far have focused on transitional instances in his protagonists’ (and his own) nascent understanding of self-determination.
“Change is a good way to say something about people,” Raiff said. “In my first film I wanted to talk about the pain of leaving home and growing up. And ‘Cha Cha’ is about how your twenties are this time, if you’re lucky enough, where you might find out who you are.”
Pondering when he felt his own inner party had finally begun, Raiff revealed that it happened when he decided to take charge of his conflicting emotions towards his parents.
“My party started when I sat my ass in therapy a month and a half ago,” he said. “I made a movie about what your twenties were supposed to be like, but I had no idea what they were supposed to be for. It was easy to make that movie because he didn’t give an answer.”
Having now built up enough confidence in his driving skills, Raiff is cautiously optimistic about where he is today, personally and professionally.
“Directing is now the thing I love the most, almost more than writing. Even though I feel very inexperienced at it, because I only did it for a total of 40 days,” he said with a laugh.
With that in mind, I asked him when or how does he consider coming of age? “When you discover who you are, that’s when you become an adult. When you can take responsibility for yourself and others,” he said, and started to pick up the phone to look up a quote about maturity from a character in the movie “Lars and the Real Girl.” He reads:
“There’s still a kid inside, but you grow up when you decide to do right, okay? And not what’s right for you, what’s right for everyone, even when it hurts.”
Raiff’s upcoming outing, a father-son saga based on a true story set in the world of hockey, will continue to address the interpersonal dynamics of asserting yourself. But he’s taking things slowly, making time to find fulfillment off-set: around loved ones or writing alone.
“When ‘Cha Cha’ did well, the first feeling I had was relief – I’ll be able to do another movie,” he recalled. “This feels like the success that I get something from, because I know the next one, longer, I’m going to feel comfortable doing what I love to do.”