comedy writing

For Flatbush Misdemeanors’s Kevin Iso, Interesting Beats Funny

Kevin Iso on Flatbush Misdemeanors. Photo: Vanessa Clifton/Showtime

Showtime’s Flatbush Misdemeanors isn’t afraid to take its time. The not-quite-buddy comedy, which premiered its second season in June, features the high-stakes story lines of a gripping drama, but neither its jokes or plotting feel rushed. Its immersive Flatbush universe feels lived in and rewards patient viewing with grounded storytelling, earned character development, and comedy that flows naturally from these pillars.

Consider the arc of protagonist Kevin, played by comedian and co-creator Kevin Iso. He’s a struggling artist crashing on his friend Dan’s couch — played by fellow comedian and co-creator Dan Perlman — when a routine food delivery to a drug dealer’s apartment goes sideways and lands him in danger. It’s not immediately clear why he’s determined to continue down this path of adversity, but when he moves back in with his parents at the start of the new season, his motivations become apparent.

As an actor, Iso is well suited to executing this slow play. He embodies Kevin with the unhurried demeanor of a person who has just woken up at noon, and his deadpan delivery is deceptively expressive enough to sell the show’s naturalistic dialogue and convey his character’s complex underlying emotions. Off-screen, Iso prefers to move at his own pace, too. He performs stand-up — material he’s in no hurry to clip and release online until he can present a full body of work — and he writes on HBO Max’s That Damn Michael Che, the second season of which premiered in May, where he feels free to showcase his sensibilities. Ahead of the premiere of season two of Flatbush Misdemeanors, Iso spoke about the season’s story lines, honing the show’s distinct comedic rhythms, and how That Damn Michael Che discovered its voice in its second season.

Early in your career, you started off performing in Houston at Ali Siddiq’s comedy club, the Horn. On the new season of the show, you hired Siddiq to play your dad. How did it feel to have that full-circle moment?
The week we filmed the second episode, I was on a high. I was sad after we finished filming on the last day because there were so many little moments like that during the week. I got booed at the Horn when I was performing there, so to come back around 12 years later and be able to tell Ali “Come play my dad” was beautiful. I brought in the homie Bryson Brown from Houston, and he got his first TV spot on the show. Imani Lewis, who plays Honor, does a fantastic job. Ray Anthony, who plays Mr. Lee, is great, too. Sometimes I won’t know how good an actor is until the edit.

I was watching Ken Burns’s Jazz documentary, and there’s this part where they’re talking about the singer Sarah Vaughan. Dizzy Gillespie was like, “She sings notes that people can’t even hear.” When I was in the edit, looking at certain scenes between me and Imani, or between me and Ray, or the way Ali added humor to his character, that’s how I was feeling. I was like, Damn, they did shit that I couldn’t see in the moment. That was so beautiful, we have to keep that in there.

A big part of your character’s arc this season is that his parents aren’t especially supportive of his artistic ambitions. Is that what it was like when you told your parents you wanted to pursue comedy?
Something I feel doesn’t come across in that episode is that my parents actually gave me a chance to pursue this. But it was after I gave them what they wanted by going to school and graduating college. After I did all that, it was like, “All right, now I’ve done the thing for you. Now let me do my thing, and let’s see how it works out.” But they were definitely afraid. I have to imagine that if this didn’t work out for me and I was back home, that’s all they’d be saying: “What are you doing? What are you doing? You’re not funny. Stop trying.”

The older I’ve gotten, the more I’ve actually come around to my parents’ perspective on this topic. Has your thinking on this evolved at all over the years?
I think it’s more of a generational thing. If you go back enough time and somebody said that they wanted to work in medicine, people would probably be like, “What the hell are you talking about? Medicine? We don’t need that.” So even now, if I were to have a kid and they were in the house all day, talking about fucking digital real estate or gaming, saying, “I can be the best Minecraft player in the world or make a million dollars playing Call of Duty,” I’d be like “What the fuck are you talking about? Get off of the game!” It’s just that times change. Some people evolve, and some people don’t.

I like the idea that your hypothetical kid is obsessed with the metaverse, and you’re like “Write some damn jokes, why don’t you?”
Yeah! It’s like, “Get onstage. Go outside and make music. Be an artist. Do something weird.”

Were there any real-life inspirations for the character Mr. Lee, the supportive high-school teacher who encourages your talents and lets you paint in his garage?
It was a combination of several teachers I had. I had a fifth-grade teacher, Mrs. Pierce. She was one of the first teachers who was extremely supportive of me and my bad behavior. Then I had a basketball coach, Coach Morrison. All the other coaches wouldn’t play me — or they would play me, but they’d take me out if I did something stupid and make me feel like a fucking idiot for turning the ball over or something. Coach Morrison would also make me feel dumb, but there’d be some sort of joke behind it, so I could laugh at it instead of just feeling silly and stupid. It’s a combination of them.

Between your show and Abbott Elementary, it’s cool that there are two shows on TV right now depicting teaching in Black neighborhoods. I saw a clip of Quinta Brunson shouting out your show to LeBron James during her appearance on the Shop. How did it feel to learn LeBron knows your show exists?
Yeah, that was crazy because I don’t think he did know. The look on his face while he was listening to her, I was like, This nigga don’t know what she’s talking about! But it was dope because I was watching it without knowing. I was like, Oh shit: Quinta, Donald Glover, LeBron James, and Lamar Jackson? I want to watch this! And then she said the name, and I was like, No, she didn’t just say that. She didn’t just say that in that room. Hold on. I rewinded it four times just to confirm she really said that shit.

Watching the show, it doesn’t seem like you feel a necessity to meet a quota of a certain number of jokes per page. How did you arrive at the show’s distinct pacing?
Trial and error more than anything. When we started making the show, at first it was trying to figure out how to get the jokes in. After a while, it went from that to “How do you complete a story?” If you watch Ali’s comedy special The Domino Effect, the reason it’s so good is that it’s so interesting. It’s not just that it’s funny. It’s not that there’s mad jokes. It’s just so fucking compelling. I’ve been watching Ali since I was 18 years old, and that always stuck with me: It’s harder to be interesting than it is to be funny. Anybody can sit there and write a joke, but not everybody can hold your attention for an hour and a half with a story. We try to funnel that realization into the story on Flatbush, and then we’ll go back and figure out the jokes.

A big theme this season is Dan’s journey through addiction and recovery. What went into crafting an authentic representation of that process?
One of the writers in the room this year is a recovering addict, and he brought a lot of realism into what it’s like to go through that process, what it’s like to be in those rooms, and who these people are. They’re all funny. That’s his whole thing; he’s like, “I’ve never laughed as hard as when I’ve been in a meeting.” We trust his point of view on what it’s like and what the lifestyle is. We wanted to have the comparison between what it’s like to be an addict of a drug and the addiction to selling it and supplying it that dealers get wrapped up in.

I wanted to talk a little bit about the new season of That Damn Michael Che that you wrote on. Between people who worked on the Flatbush Misdemeanors webseries or the Showtime show and people who write on and/or have appeared on Che’s show, I counted nine people who overlap! Is there an explanation for that much crossover?
We just fuck with each other! We’re trying to keep the money all in the house. For the most part, it’s just easier to work with people that you know and that you trust can deliver — versus actors that may be able to get the acting down but not the comedy down. Like, when we got Jackie Fabulous, who was on Che’s show this season too, we were looking for somebody who had comedic rhythm and timing and could add jokes we didn’t already have. A rare person who was able to do both this year is Zoe Winters. She’s a hidden gem in the show. I thought she did comedy. I was like, “You have to do improv or something.” But no. She was on Succession but doesn’t do comedy like that.

I heard Michael Che talking to Seth Meyers about how he didn’t really know what the show was in its first season and how he developed a better understanding of the show’s voice this time around. Did you feel that shift in the writers’ room?
Absolutely. For one, it was just more free-flowing because it was our second time doing it, so the pressure was gone. I know we felt that on Flatbush, and I’m sure Sam Jay felt the same thing on Pause. Going in with Mike this year, from the very beginning it was just, How do we make it funny? We’d bring the silliest sketches to the room and he’d be like, “Oh, y’all gotta figure that out.” The emphasis was just on being as funny as possible because we knew the messages would come through later.

For Kevin Iso, Interesting Beats Funny