How ‘Cha Cha Real Smooth’ Director Cooper Raiff Forged a Unique Collaboration With Dakota Johnson

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When Cooper Raiff pitched Dakota Johnson on a film about a college grad who’s great at starting bar and bat mitzvah parties but clueless about starting his adult life, she was immediately in.

There was just one problem: he didn’t have a script.

Still, the idea of Cha Cha Real Smooth” – inspired by something his mom once told him about how raising his disabled sister had shaped her life – was strong enough for him to bluff his way through.

“I think I do the best work when I’m just entirely focused on writing one thing and telling people, ‘I can’t talk for two weeks because Dakota Johnson thinks I have a script I don’t have,’” Raiff joked in an interview with TheWrap.

In “Cha Cha Real Smooth,” which takes its name from the classic b’nei mitzvah bop, Andrew (Raiff) finds a kindred spirit in an outcast mom named Domino (Johnson) and her autistic daughter, Lola (Vanessa Burghardt). As one party blurs into the next, they develop a unique connection: that of two people standing together at different crossroads in their lives.

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As a filmmaker, Raiff is not only unafraid of the awkward transitions between major life changes – he’s drawn to them. His first film, “Shithouse,” was about a freshman who struggles with moving away from home and finding his place in college.

“I think it’s always those transitional moments, [those] conflicts that tell you a lot about people and about what they’ve been going through,” said the writer-director-actor. “Also, I’m just really interested in making a movie about a time in my life that I haven’t shed yet.”

Indeed, the now-25-year-old was a sophomore in college when he tweeted the indie filmmaker Jay Duplass, daring him to watch his DIY project that became the basis for “Shithouse.” After Raiff dropped out of college to make the film, it went on to premiere at South By Southwest, where it won the Grand Jury Prize and was acquired by IFC.

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“Cha Cha Real Smooth” debuted on an even bigger stage, nabbing the Audience Award at January’s Sundance Film Festival. Apple picked up the film for a cool $15 million.

Raiff’s dizzying ascent doesn’t exempt him from feeling out of his depth sometimes; after all, he’s directed for a grand total of 40 days.

What he lacks in experience, he’s been able to make up for with an eagerness to learn and careful attention to “things that are probably really small in the grand scheme of things, but I care so much about them,” he said, adding: “I just feel really lucky and grateful and I’m trying my best.”

Read on for TheWrap’s full conversation with Raiff, in which he discusses why Dakota Johnson is his favorite actress, how he got the rights to Lupe Fiasco’s “The Show Must Go On,” and what he’s looking forward to about his next film.

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I read that you did not, in fact, have the script written when you pitched the movie. How quickly were you able to get that together?

It makes for a good sound bite, but I [started] writing this character, this mom of a disabled kid, when I was, I think, a freshman in college. It was based on something my mom told me one time about my sister who’s disabled. She said, “You know, my life has really been defined by her stages, and always will be.” After I made “Shithouse,” people were asking, “What movie do you want to make next?” By the time I met Ro [Donnelly], who’s Dakota [Johnson]’s producing partner, I had formulated enough of a pitch where I was like, “It’s about this 22-year-old – the only lens I know how to tell a movie [through] is a 22-year-old dumbass kid – and this mom, Dakota should play the mom. There’s bar mitzvahs involved, and it’s called ‘Cha Cha Real Smooth.’” But I didn’t have a script in any way.

[When] I met with [Johnson], it was super late for her because she was in Greece, about to shoot “The Lost Daughter.” We really hit it off. By the end of it, [she and Donnelly] were like, “We want to do it, send the script.” And I was like, “Oh, let me go make sure it’s good first.” So I went away for a week, I think I wrote 60 pages. [When] I sent it to them I said, “I don’t really like the last half very much, so just give me another week on that.” By the [end of the] two weeks, I had sent them the whole rough draft. I think I do the best work when I’m just entirely focused on writing one thing and telling people, “I can’t talk for two weeks because Dakota Johnson thinks I have a script I don’t have.” So it was kind of nice to have that protected time to just fall into writing that. After I sent it, they were so great about being my script buddies. We sent the script back and forth so many times in such a short amount of time, really. The ultimate script was finished and we were going out to financiers within three months.

Why did you have Dakota Johnson in mind for the role of Domino?

Dakota is my favorite actress. She’s got such a specific set of tools that she uses to do incredible, complicated things. And she’s so engaging and watchable. I think a lot of people, when you’re watching them on camera, feel like they could maybe float away. She’s not leaving and I’m just obsessed with that quality of hers. She’s very sharp and smart and openhearted and never forces a single thing, but also she’s very comfortable with having moments. I see some movies she’s in that don’t let her have that to the extent that I know that she could. When I pitched her just [said], “I really want you to develop the character with me, and I want to not just highlight what you do best, but give you space to do all the things that you’re so good at doing, yada yada.”

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What were you looking for in the actor who was going to bring Lola to life, and how did you know that you’d found it in Vanessa Burghardt?

We did a wide search for all three kids, David (Evan Assante), Rod (Colton Osorio) and Lola. I think I was really just looking to fall in love with these kids and have them inspire something. With Vanessa, what was so particular about watching her tape was it was not at all what was written on the page. She did this one minute interview portion for the audition, and I just fell in love with her. I started crying really hard and I didn’t know why. I called [Donnelly] and said, “I know this isn’t what’s on the page but Vanessa is gonna play Lola. And I don’t want to have a single argument with any of the producers about this, because I’m going to make it work and just trust that I’ll figure it out.” [Burghardt] is just a bit older than what we thought Lola was going to be and so I had to change the fact that she is older than the kids in her grade, she’s taller. And [she and Johnson] look like siblings a bit. But really the process was me trying to catch up to Vanessa the whole time, just keep up with her as a person. That’s how Lola came to be.

Something I’ve really liked about both of your films is that they take transitional phases in young people’s lives seriously, and treat them with real empathy. Aside from sharing an age with your protagonist characters, why do you gravitate toward this subject in your writing?

Starting with a transitional phase can really highlight what the next phase is supposed to be, but also how your life has defined you leading up [to] this point and why you’re scared to go into this new phase, or why you need someone to help you get strong for it. One thing that I’m working on now [is about], “My dad is starting a new family so that’s bringing up a lot of stuff inside me.” So I think it’s always those transitional moments, [those] conflicts that tell you a lot about people and about what they’ve been going through. Also, I’m just really interested in making a movie about a time in my life that I haven’t shed yet. Like when I made “Shithouse,” I was still very much connected to the people who held me up [in college].

I don’t like when 40-year-olds make movies about high schoolers because I think a lot of times, college or high school is used as a playground for [people] to do whatever funny thing [they] can. It’s not that they don’t take it seriously, it just feels [disrespectful] because there’s no real reason [to make it] other than “High school is relatable.” When I wanted to make a college movie, it was only going to be about one thing, and that was the pain of leaving home and growing up.

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Yeah, it feels ironic, because those periods of life are fraught with the most unglamorous, awkward situations and emotions. Also, I find that the way digital communication is integrated or not integrated in a movie about young people is pretty telling in terms of who made it. Is that something that you even have to think about as a filmmaker? 

It’s funny, that’s the one thing I don’t think about. I mean, I do think about how best to not just show someone texting, like we did voice messages for “Cha Cha” to make it so you don’t have to look at a phone the whole time. But I was watching the first episode of “Conversations With Friends” on Hulu the other day, and the way that they [depicted] texting, I was so grateful for it. For us, watching someone text in real time, that’s drama. Watching the bubbles pop up, it’s not just information. Sometimes you show a text because you’re trying to show a plot thing really quickly, but even if you’re doing that I think you can get into a little bit more. And it is what we do most of the day.

I wanted to ask him about the bar and bat mitzvah of it all. I love the humor and the pathos that that setting brings out, and how Andrew comes alive in this environment that’s not meant for him, where all these kids are working through puberty and middle school. What about that setting was fertile ground for exploring the themes you were interested in?

Well, I loved [the idea of] this 22-year-old who doesn’t know who he is and is not a man, working these parties where these people are becoming little men. I think I really feel spiritually aligned with these 13-year-olds. It was also a way for Domino and Andrew to keep meeting back up. When I had the idea of the bar mitzvah circuit, the party starter idea came to me, and the whole idea of Andrew being really good [at] starting other people’s parties, but not even having any idea how to start his own. It just helped clarify what I wanted to make the movie about while being fun and awkward. I had my first kiss at a bar mitzvah and I was so excited to put that in the movie.

I’ve always thought that bar and bat mitzvahs are great musical time capsules. Were you trying to convey a particular year or era with the song choices? And is there anything that you really wanted to include that didn’t make it in?

Yeah, there was a lot. The movie opens in 2011 and so the Lupe Fiasco [song] “The Show Goes On,” I really had to fight hard for that. I wrote a letter to Lupe, because we didn’t have the money to afford it. It was important to start with that so that the rest of the movie can be cheated to, “If we started with this, then this is the real world.” When we came up with the idea for “Funkytown,” it was just [us] trying to find a song that was cheap enough that everyone knew. I really wanted “24K Magic” by Bruno Mars because that’s a song that always gets me on the dance floor. Even in the opening flashback scene, I really wanted to do the stanky leg because that’s what I really remember the most [from bar and bat mitzvahs].

Yeah, and the cat daddy. 

Yeah, and the jerk or just songs that have those dances. But we just didn’t have the money to do a lot of the things that we wanted, so it was kind of just the music supervisor, Rob Lowry, helping us find a lot of library music that felt correct.

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This is your second time starring in a project that you also wrote and directed. Do you find it challenging or helpful to be wearing all of those different hats at the same time?

It’s a lot. The next movie I do, I won’t do that just because it is physically just exhausting. But I don’t think of it as different hats, I think of it as one big hat. As a director – like with this next movie – I want to be as emotionally available as I would be if I was on camera. It’s just nice to have the perspective [of a director]. You don’t really have that much perspective when you’re acting in it [too]. I like that to some extent, because as a director, I just want to be as close as possible to the actors, and the way to be closest to them is by being in the scene with them. I really thought of Dakota as not just my script buddy, but [also] my director buddy. When we were in scenes together, it felt like we were both directing and trying to figure out what was working and what was the funniest, what was the most dangerous, what was feeling the most alive. And when I was directing scenes with her that I wasn’t in, it didn’t feel right. She was like, “What are you doing behind a monitor? Get over here.”

The way you got your start reads like an indie movie fairy tale. I’m curious about how you came into the confidence to just go out and make a movie, being thrown into the deep end like that. Do you ever experience imposter syndrome, or by now do you feel like you have more of a handle on things?

I feel both. With “Shithouse,” I asked like 10 people to direct that thing, and at some point, I realized that no one wanted to direct my small-budget college love story. But on day five of making that movie, I realized that I do love directing, and that [it’s] the thing that combines [everything] I love to do. Not only do I feel impostor syndrome, but I just feel so inexperienced as a director, and I’m really excited to gain experience. I also think the big thing is, I don’t put a lot of pressure on myself to be this amazing director. The truth is, I’ve directed a total of 40 days. I feel confident as a writer, because I’ve been writing for a bit more time. But [with] directing, I just feel like I’m constantly learning. I’m always just over here, trying my hardest.

In “Cha Cha Real Smooth,” you directed a mix of veteran actors and newcomers. Do your age and relative newness to the industry provide a helpful perspective?

Yeah, I’d see it in everyone’s faces. Leslie [Mann] was very invigorated by a young person trying to direct a movie that she’s in. I could just tell that she was like, “Oh, this kid is really passionate about what he’s trying to say with the movie.” It was so personal to me. And I think she’s like, “That’s so sweet,” and really wanted to help. I think it’s not really the perspective, but the energy and the care and passion about things that are probably really small in the grand scheme of things, but I care so much about them. And it’s like, “Why not care a lot about this movie called ‘Cha Cha Real Smooth?’” [laughs].

This interview has been edited for length and clarity.

“Cha Cha Real Smooth” opened in theaters and began streaming on Apple TV+ on June 17.

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