Interview: Writer/director/actor Cooper Raiff gets his groove on with ‘Cha Cha Real Smooth’

It has been a crazy start to the career of Cooper Raiff, the talented writer, director, editor, and star of the 2022 Sundance Audience Award winner, Cha Cha Real Smooth.

Back in March of 2020, Raiff and his team were about to present his feature debut, Shithouse, at the SXSW Film Festival in Austin, TX, the state in which he grew up in. But as we all know, the world was shut down due to COVID-19, thus SXSW was canceled, as well as the premiere of the film. But that didn’t stop the SXSW jury from awarding him the Grand Jury prize, thus catapulting the film and himself as a new name in the business to look out for.

Flash forward to earlier this year, when it was announced that Cha Cha Real Smooth was going to be part of the 2022 Sundance lineup. But with the Omicron variant forcing the festival to go one hundred percent virtual, Raiff and company had yet another premiere setback. But the film was a hit, and two months later, in an unplanned, unexpected full-circle moment, at the 2022 SXSW Film Festival, Raiff was able to show his sophomore effort to a full crowd for the first time, with his family and friends in attendance.

Being there that night, I could sense the overwhelming emotion on his shoulders, as if it was both a sigh of relief and a jubilant moment he would never forget. In those moments of him introducing the film, you understood why critics and audiences have fallen in for his films, as he might be the most genuine, kindest soul of his generation in Hollywood working today. His art reflects who he is, and as I stated back in my review of Cha Cha Real Smooth from Sundance earlier this year, the film is one of the best of the year because of “the sensitivity and earnestness Raiff has behind and in front of the camera.” At the ripe young age of 25, he shows the promise of being someone who will be around a long time, giving us honest, authentic films with every effort.

I sat down with Raiff recently, as we discussed his inspirations as a writer-director-actor, his process in making his films, working with co-star and producer Dakota Johnson on Cha Cha, what has it felt like to go through everything over these last two years, and what he thinks defines a “Cooper Raiff film.” We thank Cooper Raiff again for his time and hope that everyone sees Cha Cha Real Smooth this weekend.

Ryan McQuade: It’s good to talk to you. Are you in LA right now?

Cooper Raiff: I am in LA. Yes.

RM: Awesome. Well, much love from your home state of Texas.

CR: Right on. Where are you?

RM: San Antonio.

CR: Awesome. I go to San Antonio all the time.

RM: Really? Cool.

CR: Yeah.

RM: First off, I want to ask you is, has film always been something that you wanted to do? I know with our generation, it always feels like you want to go online, or you want to do something digital or whatnot, and film seems to get sidetracked.

CR: I wanted to … I really loved movies. I think I always wanted to be a part of making movies. I first thought, I never wanted to be a director. And I, at first, didn’t want to write. I was like, “I’m going to act. That’s my way to be on a movie set.”

But then in high school, I started writing some, and I had a theater director who was really awesome. I wrote a play, and then I was like, “I should do theater.” And then, I think she, one time, was like, “I think you’re more of a movie writer because it’s a lot of small things happening here. Not a lot of meaty stage moments.”(laughs)

So, then I started writing a little bit. I was having a really hard time figuring out how to get on a set or get people to read what I was writing. So, I just made something, and I really truly didn’t even think of it as me directing something. I just made it with my two friends. We all made it together as a homemade movie. I was booming my girlfriend in scenes that I was acting in with her and my friend, who had never held a camera before, and was filming it on this really crappy camera that had dead pixels and was falling asleep while on film. It was just a homemade movie.

After that, I got hooked up with Jay Duplass as my mentor figure person. He, at some point, just said that “Even at this stage, the cavalry isn’t coming. You still have to make your own stuff. That’s the way to do it.” That’s why I directed my first movie, Shithouse. I think that’s why I’m into filmmaking.

RM: Speaking to that too, it seems like you’ve had the film bug in you for a while. Were there films that inspired you to start making films? Were there any specific films that you were inspired by, or that you watched in your preparation, or as you were filming Cha Cha Real Smooth that influenced the film?

CR: Yeah, for Cha Cha, I really loved Almost Famous a lot, and Lost in Translation is a movie that really made me want to be a writer because I really loved Sofia Coppola’s writing and how she’s really saying stuff with the smallest relief, like the funniest moments. When I was younger, I really liked Andrew Garfield and The Amazing Spiderman.

RM: Really?

CR: Yeah. And I really loved Bridge to Terabithia when it came out. Those were movies that I was like,” oh God, I really want to be a part of movies and so fun.” And then I think at some point, you’re like, “okay, I can still be involved in movies, but I definitely probably won’t be involved in Spider-Man.” So I’m going to be interested in smaller movies and things where I think I can write a scene where a dude’s on an elliptical and he gets stuck and he is like,” Help.” And it’s so meaningful, like that scene when I watched it in Lost in Translation, I was like, I wanted to be a writer. And it’s such a… I don’t know. The way she (Coppola) conveys her things are so fun and awesome.

RM: I’m curious for you, you have had, over the last two years, the most unconventional start to anyone’s career with the premieres of your two films, because you have set them all up, one’s going to go to South by Southwest, the other one’s going to go to Sundance, and then obviously, COVID and Omicron variant happened and you have to go the virtual route. So, I wanted to ask you, because I was there the night of South by Southwest this year when your film Cha Cha Real Smooth premiered…

CR: Oh, awesome.

RM: What did it feel like for you to be in that room with your friends, your family, and everybody there to see one of your films on the big screen with an audience?

CR: I think I said it that night. It really felt like the best night ever. It was the first time where I felt like I was enjoying the work or whatever. And because our first South by Southwest… was it two, three years ago, I don’t even know. But when it got canceled, it felt like, “okay, I feel so lucky that we got into the festival and it won an award and we opened doors.” And so it felt like the best experience, even though I didn’t get to watch it. I really put my head down and sat and thought of it as the best thing.

And then when Cha Cha got into Sundance, I was so excited to see it, but still hadn’t been to a film festival, so I didn’t know what to expect. And then when that got canceled, I had this instinct to just put my head down again and be like, “all right, let’s go on, move on, make the next one.” But then that night (the 2022 SXSW premiere), felt like I was finally stopping and enjoying the fruits. And it was so nice to watch it with the cast. And it was so nice to watch it next to my mom. It was a really magical experience.

RM: How have you felt about the reactions to both of your films, given they are being seen in such untraditional ways?

CR: It’s tricky. I really hold that night at SXSW up really high, and that felt like the thing that I really, really wanted for Cha Cha, and what I wanted to get out of it and what I wanted to hold onto is that experience. And I’m going to try not to involve myself much in the platform release and what people are saying virtually, but yeah, it’s been interesting to feel like people have opinions about the movie and people like the movie, people hate the movie, people like the title and people really hate the title. And I try not to read about it, but I do. And I think the goal is to not let it move me in any way and just keep trying to make movies for that SXSW experience and to watch it next to my mom and the people that I’m close to and people that I made it with.

RM: Absolutely. Transitioning over to the film. I’m curious, I know that you wrote the script on time constraints and everything because you sold it and you didn’t have it written and everything, but when did you come up with the initial idea for the film? Before the pitch, before you were speaking with Dakota and everybody over at TeaTime Pictures?

CR: When I was probably a sophomore in college, I started writing this character that was just this mom of a disabled kid. And it was inspired by conversations I had had with my mom about… My sister’s disabled and I know she has a very particular experience and sometimes she will let me in on certain things that are really big. And I feel like I have no choice but to write them down because I don’t know how to process them.

And so I started writing this character and then after I made Shithouse, people were asking, “what movie do you want to make next?” And I really wanted to do this TV show, but when they would ask what movie I’d be like, “oh there’s this character that is a mom of a disabled kid.” And it’d be like, “that’s not a movie, that’s a character.” And then over time, I think I came up with a pitch of centering that movie through on a lens of the person I know best, which is just like a 22-year-old dumbass. And so I was starting to pitch that relationship, and then when I had to think of the idea of how they keep coming into contact, that’s when the bar mitzvah idea came.

RM: What was the biggest difference, either in front or behind the camera, that you saw in yourself in making this second feature?

CR: I had this big packet that had all of the possible directions that exactly what I wanted to say with each scene and what I wanted to keep in mind. Because I knew from the first movie that it gets really exhausting. And so, when you’re so tired, you’re not really thinking about what’s the exact intention of this beat or something. And so, I would go to that, those bullet points and remind myself. And the other big thing was just the trust of who I was making it with. Like I really made Shithouse in a vacuum and with Cha Cha, I was looking around and I could tell that people really cared about it in the same way that I did and had as much stake in it as I did. And so, it’s just trusting that I’m not making it on my own. And like people, people care about it getting finished.

RM: You are putting on multiple hats when you make these films. And so I’m curious how you find a balance in juggling being the writer, the director, the star of this film, and then also too, as a director, how do you judge your own performance as you’re putting this film together? Do you have to compartmentalize three different things?

CR: It’s definitely not a bunch of hats that I’m constantly changing. It just feels like one big thing and it’s tiring, but it’s… I’m never, as a director, you’re not judging a performance. You’re just trying to figure out what feels the most alive and dangerous and funniness. So, it always felt like they were all the same thing. Like the next movie I make, I’m not acting in it, but I want to be just as emotionally available as I was as an actor in it. Like if I’m crying in a scene as an actor, say I’m not acting and I want to be crying behind the monitor too, because I think that that’s what I really want the actors to feel. Like I’m on the floor with them.

And if they’re in front of the camera, just like dying, I don’t want to just be like, “it looks great.” I want to be there with them. And so it’s tiring. I don’t want to do it again, but I think it’s easier than just constantly trying to have perspective. Cause I didn’t have any perspective and I love that about it. That I’m just so inside of it. And the perspective part comes, I think in editing. When you’re filming, I think it’s hard to really zoom out.

RM: There’s a great amount of, I think, vulnerability and relatedness in each one of your characters within your films. Is it just on the page or when you cast the actors and you guys are going through everything, you are then adding things from their perspective, retooling those characters to fit them?

CR: It’s entirely just trying to keep up with whoever I cast. Like when someone like Leslie Mann or Vanessa Burghardt or Evan Assante, like all of them, when they came in, everything changed. And I was always just trying to figure out what would work best and how the marriage between the actor and the character would work best. And, and luckily, all the actors were super excited about that too. Cause I think actors want to say things that they want to say and it’s silly of me to think that they were like, “yeah, I want to do this movie. And they loved every part of it”. I think it’s important to listen to what they want to do and listen to what they think their strengths are.

RM: Speaking of your actor, what was it like collaborating with Dakota Johnson, not just as a fellow actor, but as a producer, as well as on this film?

CR: It was a roller coaster. She was there the whole time, from the beginning. She helped with the script and she was on set and it felt like we were brother and sister arguing about blocking and then all of a sudden we were in a scene playing soulmates. And so it was a roller coaster, but it was nice to have someone who cared about what the movie was saying. And about the outcome of the movie.

RM: You found two amazing youth talents in Evan and Vanessa. Can you talk about the audition processes for both of those and what it was like to work with them as well?

CR: Yeah. With Vanessa, when I watched her tape something, I still don’t know what happened, but it just really profoundly affected me. She was reading with her mom, and I could tell they’d never leave each other’s side. And it reminded me.. it just triggered something in me to where I was like, this is the person that I want to work with on this movie. And this is the heart of the movie, and I can’t wait to meet her mom. And we did a callback, but I knew it was going to be her.

And I told Ro (Donnelly), the producer, that I don’t want to have… Because the thing was Lola was written in a very different way. She wasn’t as old and there were certain things about her that Vanessa was so different than what I had written. And I told Ro, I don’t have any arguments, it’s her and I’m going to make it work. And that’s that. And that’s what we did. And I’m so glad everyone let Vanessa guide the movie in that way. And the same with Evan, Evan was… honestly, Evan was so similar to what I pictured and just the way he brought it to life was so his. Just he really is so similar to David. And so he just nailed it.

RM: Yeah. I just loved those scenes together with both of those actors with you with that, especially Vanessa with you, there’s just so much heart to them and its beautiful stuff that you guys do together.

CR: Thank you.

RM: One of the credited composers on the film is Este Haim. How did she become a part of the project and what was it like working with her?

CR: She’s the funniest person alive. And when I heard her for the first time, I was like, “you need to go into a comedy or some sort.” She’s really, really fun and awesome, and so sweet and so talented and Ro Donnelly knew her partner, Stray, Christopher Tracy, for who they both did the score. And so, I think they had just done the score for this show called Maid. And Roe had me watch that and I was like, “I love it.” And we met with them and it was a really fun time working with them because they loved to collaborate and they are so talented.

RM: Yeah. That’s great. Last question I have for you, which is while you are young and not even close to the prime of your career, every artist thinks about what they want their art to say. So, when someone sees a Cooper Raiff movie, what do you want them to take away from the experience and what do you want them to take away that it says about you, yourself, as the writer, director, and star of this film that you created?

CR: I think a really specifically good feeling that I want when the credits roll, I really want to… I’m really so in love with the characters and I really want them to be somewhat in love with the characters and to have some understanding of… Yeah, I got… I don’t… it’s a big question, but I think the main thing is just the reckless abandon of I’m so shamelessly in love with… I’m probably going to be crying harder than you are watching the movie and I want that to come through if possible.

RM: Well, that heart and that passion is in your films and this movie, I’ve seen it twice. It’s fantastic.

CR: Stop it. Stop watching it. (We both laugh)

RM: It’s one of my favorite films of the year. I can’t-

CR: Thank you.

RM: I’m going to probably watch it again this weekend so I can show my family and-

CR: You’re going to hate it the third time. (Laughs)

RM: No, I’m not. No, no, no. (Laughs)

CR: Well, thank you.

RM: Safe travels and I hope everyone gets to see this wonderful special film that you’ve created.

CR: I really, really appreciate it. Thanks so much for your time.

Cha Cha Real Smooth premieres in theaters and on AppleTV+ June 17.