Cooper Raiff: Director of Cha Cha Real Smooth–Next Big Thing

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 has its drawbacks. He moved into a new sublet in Queens last week.

The temporary living situation is not an atypical experience for a 25-year-old in New York City. The move coincided with the release of Raiff’s second feature, 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.

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 after his film 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 has 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. 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 a big company.

That’s only amplified Raiff’s dream-like state, which ramped up after Apple, having newly steered Sundance darling “CODA” to Best Picture Oscar, wrote a big 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.”

Jay Duplass

Raiff made a scrappy 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 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 feature-length. It premiered 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.”

After winning the festival’s top prize, he took a lot of 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 an idea that developed into a 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 (Vanessa Burghardt).

Small Movie about Small Things

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.

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Raiff and Johnson have a flirty friendship in “Cha Cha Real Smooth.”Courtesy of Sundance Institute

Raiff drew inspiration from his own life; his younger sister is disabled and can’t walk or talk. “It really rocked my parents, 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 sensitive characters who feel comfortable openly shedding tears and talking about feelings. “I cry a lot,” Raiff says of his reality. “I’m not trying to start a revolution.”

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 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.’”

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.

First Kiss at Bar Mitzvah

He went to a small school, which by his estimation had 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 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. 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 in the world of hockey.  He’s been meeting with studios and distributors, hoping 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, 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.”

Raiff wants to remain selective in the projects he takes on: “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 chasing: “I really want my grandma to love a movie I make. And she really did not like ‘Shithouse,’” he says. “She was like, ‘Lots of talking.’”