Jaboukie Young-White On Playing Straight, 'Fairfax' & A24's 'C'mon, C'mon'

While Jaboukie Young-White was in New Orleans filming his upcoming A24 film C’mon C’mon, he received an email about Fairfax, a new Amazon animated series about a group of four middle schoolers navigating early adolescence and hypebeast culture in greater Los Angeles. After glancing at the script, he immediately postponed the dinner he was scheduled to attend with his costars, finding it much more important to dive into his voiceover audition.

“I was such a hypebeast growing up. I wanted nothing more than the BAPE hoodie that zipped all the way up to the top. I wanted that so bad,” the Chicago-born comedian, actor, and writer fondly recalls about what drew him to Fairfax. That Truman, his charming ladies’ man of a character, was also a semi-pretentious cinephile, only endeared Young-White more to the role.

Of course, Fairfax is just one of many projects the multi-hyphenate is involved in. Earlier this year, he appeared as the straight lead of Jonah Feingold’s rom-com Dating & New York, where he played the hopeless romantic member of a friends with benefits arrangement; he also played a true crime podcast fanatic in Hulu’s superb Only Murders in the Building. Soon, he will appear in Issa Rae’s Miami-set HBO Max hip-hop comedy Rap Sh*t. And throughout it all, he’ll be working on The Gang’s All Queer, the half-hour series he’s currently writing and executive producing for HBO. Based on Vanessa R. Perfil’s book The Gang’s All Queer: The Lives of Gay Gang Members, the show will focus on “a closeted 20-something in Chicago who, grieving a gang-related death, ditches college to find closure.” After getting his start in stand-up clubs, through his hilarious Twitter, and in The Daily Show’s writers’ room as the resident “Senior Youth Correspondent,” it’s clear that Young-White’s Hollywood career is only just beginning.

Ahead of the October 29th Fairfax premiere, NYLON hopped on a Zoom call with Jaboukie to talk about the show, the inherent differences between New York and Los Angeles, why he hasn’t “pivoted to video” like his fellow young comedians, playing straight, being mentored by Issa Rae, and why he thinks his eccentric C’mon C’mon costar Joaquin Phoenix is “just a guy.”

What about your Fairfax character Truman spoke to you?

I also went to film school and totally was pretentious like that. Like, I remember being in film school and being like, “Oh yeah, that pilot that I wrote? Yeah. I'm going to produce that by the time I'm 23. 100%.” That was me. “By 25, I'll at least have made two pilots.” I was really talking like both of my parents were rich and in entertainment. Of course, I was rudely awakened.

On the other hand, I imagine that you and Truman have vastly different approaches to social media. Truman is all about refinement and curation while you are famously known for your reckless tweeting. What would Truman say about your personal social media strategy?

Truman would have a lot of opinions. First of all, he’d tell me that I need to pivot to video. Nobody wants to read text anymore. Fuck words, that's old. Now, people are all about video. I think that would be the number one thing. Also, he’d probably tell me that I really need to chill out on Twitter a little bit.

I think a lot of your contemporaries in the comedy space have made that pivot to video, especially now with TikTok and Instagram Reels. Why haven’t you followed suit?

In a very old-fashioned sense, I feel like when cameras first dropped and people were like, “Don't take a picture of me! You're stealing a part of my soul,” they were onto something. I don't like putting my visage out there that much. [points to face] This is all mine. You can have my thoughts and my words — I like to freely share those things. But I'm very precious about video stuff. If you want to hear my voice and see my face and my body and my thoughts, all emotion, you’ve got to go on a streaming service for that. We’re not just giving that out. Come see me at a show or something. Come see me in real life!

So we aren’t getting any “Jaboukie’s Face” NFTs any time soon?

[laughs] Exactly. Exactly.

You’ve written for Big Mouth, which is a similar show about the awkwardness of adolescence. What do you think is so interesting and hilarious about this particular age group that lends itself so perfectly to the adult animated comedy space?

So much of comedy is trying to find a common denominator and playing with that, and adolescence is that — like, literally every single one of us experienced that. The only genuine way you didn't is, like, if you were in a coma for your entire teenage years — and even then, when you come out of the coma, you're still going to go through the awkwardness. It's something we always have to deal with. And the other thing is that it never fully goes away. There are echoes of it throughout the rest of your life. It's felt the strongest when you're at that age, but you could easily feel that same emotion again in your 20s, your 30s, your 40s, and your 50s. It kind of always just goes back to those first really intense feelings.

The other day, I was at dinner and a friend brought their kid, and I just was watching the kid experience everything. The kid was just so overwhelmed by the emotions, and I was thinking, It really is crazy because there are so many emotions that you experience for the first time in the first half of your life. It’s your first time feeling something and you have nothing to compare it to. That can be so powerful and so overwhelming because you’re feeling something so intensely. Now, you can look at it and laugh because you have that remove. But at the time, it’s really such a hardcore feeling.

Earlier this year, you came out with Dating & New York, which I think, as the title suggests, is very much a movie where New York is a character in the classic Sex and the City sense. Fairfax, on the other hand, feels like the opposite. Hypebeast culture obviously exists everywhere, but I think it really is this huge thing in Los Angeles.

It’s its own thing, for sure. I mean, if you really think about it, LA is kind of the birthplace of a lot of the modern shit going on right now. Being from the Midwest, I can claim Kanye, and he is a huge part of that DNA. But like Odd Future? That was its own thing. It was huge. The biopic in 20 years is going to be crazy.

Are you writing it?

Listen, man. Maybe! Tyler [The Creator], hit me up. Let's get to work.

Both Dating & New York and Fairfax do a very good job of satirizing their respective cities. Do you have a coastal preference and do you find one city “funnier” than the other when it comes to playing up its stereotypes?

I prefer living in New York just because I like being able to walk places and not really have a destination. In LA, if you walk somewhere and you don't have a destination, you are on the highway.

I mean, even if you have a destination in LA, you’re not walking to it.

Right. Exactly. But I feel like sending up LA is more fun though, just because you get weirder, bigger personalities a lot of the time. I think LA culture really breeds people who only interact with people who are like them, and I’ve always thought it was really funny and interesting when you can talk to someone and be like, “I can tell you're from a very specific pocket of people.”

Dating & New York was your first big lead film role, and you got to play a straight rom-com love interest. I think the role of “straight romantic lead” is quite rare for anyone who is not only Black, but also queer. How did it feel to get that huge opportunity?

It was kind of surreal — even the fact that IFC picked it up, because IFC was so formative to me growing up. But the thing I loved most about doing it was that it was fun to shoot, but was also a challenge. That was the first lead role that I'd had and I was playing straight!

But [there’s not much of a difference between gay and straight men now]. When I first moved to New York, I was like, “Wow, everyone here is gay. That's awesome!” And then, you see a man with his girlfriend and you're like, “Oh, that's your ‘partner.’ Okay.”

“Oh, all the gay people I’ve been seeing have actually been straight! Surprise!”

Right! Exactly! I think it's beautiful now that all the straight men in Brooklyn dress like Liberace and all the gay men dress like Jeff Foxworthy. The girls are giving “Git-R-Done” now!

I think there’s a huge conversation happening right now about who should play which roles. For instance, I know there are several queer actors that have come out to say they have no interest in playing straight roles. But many of your recent roles — in Dating & New York, of course, but also in Awkwafina Is Nora From Queens, and now, in Fairfax — are heterosexual. How do you feel about that?

I started doing comedy pretty young. When I was 18, I just jumped right into it. But there wasn't really that “diversity in Hollywood” push at that point, so I was just doing this shit to see what would happen. With the diversity push, there's 100% been a push to include people on the visual side of things, but I'm really interested in: What if we had agency as storytellers? As creatives? What if we had agency to tell stories in a way that, for the past 100 years of filmmaking, straight white men were allowed to tell every story under the sun? What if I had clearance to tell stories that weren't necessarily one-to-one with my life? What would happen?

I totally get why people would be like, “I don't want to play straight.” But especially because I come from a writing and acting background and am so used to performing my own words, there are a lot of times where I’m like, Okay, I'm playing this with the assumption that this is me and that you want me on this project because you want people to be like, ‘Oh, that’s so him!’ But it’s not me writing this and it’s not someone like me writing this either — so what can I really accomplish here? I’m not trying to be shady or anything. I’m just interested in doing things that are challenging and give me and other people like me more space to create things.

Speaking of getting the chance to tell your own stories, I’d love to talk about the show you’re currently writing, The Gang’s All Queer. What drew you to this source material?

I was drawn to it because, frankly, I grew up in a neighborhood like that. I grew up in the suburbs of Chicago, but I grew up on a block. But also, in the larger sense of storytelling and being able to push the boundaries, I think there have been two sides of queer representation. We had the horrible version of it for the longest time, which was like monsters or tragic figures that are punished for their queerness narratively. Those figures always end up tragically so the straight audience can realize they have the empathetical capacity to identify with a queer person and their suffering or whatever. But then, I think it pivoted in the complete opposite direction to these perfect, saintly, very friendly narratives and these kind of eunuch bestie vibes. But in dehumanization and in deification, you’re still not human in either one of those.

Then, there was also the idea of the gangster being one of the most masculine figures in the American zeitgeist — even going back to the mafia days. So many antiheroes are “manly men” who are morally gray, so I thought there would be so much to play around and fuck with by just making it gay. And this is a real thing that happens. These are real stories. I'm not just making this shit up, which is another battle when you're making stuff that doesn't neatly fall into a box.

You’re producing The Gang’s All Queer with Issa Rae, who also casted you in her upcoming HBO Max series Rap Sh*t. I don’t know much about your personal connection with Rae, but it seems like you two have definitely developed a close working relationship. How does it feel to have another Black person working in your corner?

It's insane. I still remember setting aside time every Sunday to watch Insecure, having watch parties for Insecure, so it’s crazy working with her now. It’s just so great. She’s also just so about supporting other Black creatives. The vibe and energy she gives off, it’s all so genuine. She sincerely wants to see people make the best work they can make and she wants to help people make that happen. It’s so needed, especially in this industry. I’ve relaxed a bit now, but at first, I was always like, “What’s the catch? What’s going on?” I was always waiting for the other shoe to drop, waiting for the rug to be pulled from underneath me. But Issa is great, just awesome.

You mentioned getting the script for Fairfax while you were filming C’mon C’mon, which I think is hilarious since C’mon C’mon stars Joaquin Phoenix while Fairfax features a character based on Joaquin Phoenix. Did you ever think about that connection?

[While working on Fairfax], I did not mention that I had been shooting [C’mon C’mon] right before. It hadn’t been publicly announced yet, and because you’re supposed to be mum about projects you’ve worked on, sometimes I will just genuinely forget. Also, in the materials I got to do my audition, [the Joaquin character] was not in there yet. So when I saw the script [that actually featured the Joaquin character], I was just cracking up and fucking dying.

What’s so funny is that when we were shooting C’mon C’mon, this was post-Joker. Actually, not even — this was during the Joker Oscar run, so it was peak “Joaquin as Joker” and him being that in the cultural zeitgeist. It was crazy to be around him during that time and then hear him be like, “I really like the caipirinhas at this one Brazilian restaurant in New Orleans.” Just seeing him be a normal dude was so crazy. So seeing the Fairfax character of Joaquin was even doubly funny. He has a really good sense of humor about himself, but he’s also just, like, a guy.

Fairfax premieres on Amazon tomorrow. C’mon C’mon hits theaters on November 19.