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Comedian and ‘#blackAF’ writer Yassir Lester has the opposite of impostor syndrome

His credits this year alone include Netflix’s ‘#blackAF,’ ‘Black Monday,’ and ‘Duncanville.’ As far as he’s concerned, that’s just the beginning.

Comedian and ‘#blackAF’ writer Yassir Lester has the opposite of impostor syndrome
[Photo: courtesy of Matt Misisco]
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Currently, Kenya Barris stars as himself in Netflix’s #blackAF, a comedy he created about his own extremely successful career in Hollywood.

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It seems like a safe bet that Barris would easily have the healthiest ego among anyone involved in this project.

But don’t count out writer-producer Yassir Lester, whose outsize confidence is riddled with self-awareness and fearless humor.

[Photo: courtesy of Matt Misisco]
Lester has no qualms about calling out his employer, for instance. One time, the two ran into each other socially, and even though Barris was wearing the kind of diamond-encrusted gold chain Nefertiti would’ve deemed “a bit much,” the creator still praised the five comparatively modest gold ropes Lester had on. While most people in his position might be flattered by a heavy hitter complimenting their drip, instead he hit Barris with some 24-karat truth.

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“I was like, ‘Don’t talk to me like that,'” Lester recalls. “‘Your chain right now could buy my entire life. I’m not gonna sit here and play a humility game with you.'”

Barris then collapsed into the laughing fit of a man who has everything, except a surplus of people who will reliably keep it real with him.

Lester aspires to Barris-level success one day himself. He wants to create, write, and star in his own show, and be the face of the entire operation.

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Judging by what he’s accomplished so far, he is already within striking distance of that dream.

In addition to #blackAF, he also currently writes for and costars in Showtime’s Black Monday, the show you should be bingeing right now, and lends his voice to Fox’s new animated hit Duncanville.

Much of the comedian’s rise happened because he is very funny, works hard, and can deliver the goods on any kind of TV comedy. (He once held simultaneous writing jobs on Girls and The Carmichael Show.) But it helps that Lester has had an abundance of faith in himself since day one.

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Bombing for the right reasons

Growing up in Georgia, Yassir Lester had his sights set on a comedy career in Hollywood. But the first time he actually tried to do standup at an open mic in Atlanta, at age 19, it went so poorly he decided not to attempt it again until he moved to L.A. two years later.

“It destroyed me,” Lester says. “It wasn’t so bad that I was like, ‘I’m never gonna do it again.’ It was actually the flip. I have the flip of impostor syndrome. My ego is, it’s too much. Anytime people are like, ‘I can’t believe I’m here with all these people,’ I’m like, ‘I can’t believe these people are here with me.’ When I did that open mic, I fully bombed. Because I wasn’t good. But I was just like, ‘They don’t get it. These hicks don’t get it.’ So I waited until I got to L.A. And I remember bombing there too, but I bombed in a way that felt like people still got it. When I bombed in Atlanta, I was like, ‘These people are idiots. I’m a king. How dare they?’ Because in Atlanta, the show I did was all 40-year-olds and up, and I was 19. So everything I was talking about they were like, ‘Shut up.’ And then when I bombed in L.A, I was like, ‘Oh, like, I’m just not funny.’ But they did understand the process of what my thought was supposed to be.” 

Comedy college is super affordable

Ascending the Scientology-lite ranks of UCB is one way to get a comprehensive comedy education. There’s also the option of matriculating at Harvard and writing for the Lampoon on the side, practically guaranteeing you’ll get staffed on The Simpsons. But there are also ways to prepare for a career in comedy without ever leaving the house.

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“I always knew I wanted to do comedy writing and stand-up—acting came later, by accident,” Lester says. “When I was getting ready to move to L.A., I was constantly watching Comedy Central Half Hour Presents with Patrice O’Neal, Wanda Sykes, [Nick] Swardson, and Deon Cole, and trying to see how stand-up really worked. I was also watching hella Criterion Collection movies and Wes Anderson movies and being like, ‘How do you write a comedy movie?’ and ‘How do you write a comedy TV show?’ I was watching reruns of Martin and Fresh Prince, Living Single. I just did a lot of consuming of things. I didn’t go to college. I didn’t go to some legacy comedy program or any of that stuff. Truly, everything I know or that I’ve come to do in this industry came from watching a bunch of stuff that I liked, watching some stuff I didn’t like, and then doing stand-up. And I think that because of that, I’m not saying I have a more interesting perspective or anything like that. I think I just have a different perspective.”

An idea, an idea, another idea, another idea, another idea

The trick to launching a TV writing career seems pretty simple when you consider what worked for Yassir Lester: Just consistently impress the right people by both working hard and being a good hang, until those people are in a position to hire or refer you. Lester was friends with the Workaholics guys when they were struggling YouTubers, and they went on to bring him in as a writers assistant on their show. A guy he met during his Workaholics tenure later hired him to write for Adult Swim’s Black Dynamite. The pattern kept repeating in future jobs as well. Part of the reason Lester was so successful once he made it into those writers rooms, though, stems from an ability he acquired through years of stand-up.

“With stand-up, you know immediately if a joke works or not,” he says. “Sometimes you can tweak it and it gets better, but you know pretty early, ‘Oh, this sucks,’ or ‘This didn’t suck,’ or whatever. And writers rooms are so much just like: an idea, an idea, another idea, another idea, another idea. And with stand-up, the $10 you’re gonna make that night depends on you essentially going: an idea, an idea, here’s another idea, here’s another funny idea. So I remember going into a writers room, and seeing people just sit there and be quiet all day. And I was like, ‘Wait, this person also gets to make money? Like, that’s crazy.’ So I always came in ready, because when you have to do three shows a night to potentially make $25 for the entire evening, not only are you always ready to pitch ideas and pitch jokes and all that stuff, but, like, you come in with a different intensity because you have a different ‘my life depends on this’ feeling than a lot of other people.”

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Disregarding discouragement

As Lester alludes to above, he became an actor practically by accident. He got a spot on Key & Peele because, after opening for Chelsea Peretti on tour, Peretti asked her husband, Jordan Peele, to put him on the show. Later, he appeared on Girls essentially on the strength of being a telegenic funny person in the writers room, an experience he describes thusly: “Someone pointed and went, ‘You,’ and I was like, ‘Okay.'” Those two appearances were enough that when Lester’s friend Adam Pally suggested he go out for the second-billed role in the 2017 sitcom Making History, he was able to audition by tape and got the role. Then the show bombed.

Making History was my first big thing, and it just went so poorly. No one watched,” Lester says. “And you put all your heart and soul into something, and you get all these people, all these brownnosers who work at the network or the production company being like, ‘This is it. You’re about to be a star.’ And you try not to buy into it, and then finally it just happens so much you’re like, ‘Maybe it’s gonna happen?’ And then, literally, the complete opposite happens and you’re like, ‘Noooo!’ I was in this weird mode after that. Then I went in as part of the pre-room for Black Monday. [A pre-room is a writers room for a show that hasn’t officially been ordered to series yet, an increasingly common practice.] We were doing a table read for the pilot and there’s this small role for a character who’s Indian. They’re like, ‘Can you just read it?’ So I did it at the table read, and it did well, and then they’re like, ‘Yo, you should play the part.’ And I was like, ‘Well, I’m black and my dad’s Palestinian, so I can’t be playing an Indian dude. And also, y’all don’t want Twitter coming at you like that. And they’re like, ‘Can we change it to a Palestinian dude and you’d do it?’ I was still kind of bitter about Making History. And I had thought I might just not try to be an actor anymore. Then they offered that role immediately, and I was like, ‘Okay.’ So, I’m glad I didn’t quit acting, but also … you can’t buy into any of that Hollywood madness. So much of it is just a foundation built on quicksand. If you let the machine start driving you, you will be left as a husk, and I’d rather just not be that.”

Maybe do write King Lear after all

For approximately one day this past March, every quarantined soul on Twitter was inspired to possibly write their own King Lear under the same circumstances Shakespeare is alleged to have done so: while waiting out a plague. Then came the backlash, buoyed by the idea that it’s toxic to pressure oneself into being productive during such a traumatic time. But perhaps enough time has elapsed now for hustlers to get back to hustling.

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“I know the meme right now that’s going around is like, ‘You actually don’t have to do anything during quarantine. You can just take care of yourself.’ And it’s like, ‘All right, but also: You can do something,” Lester says. “I’m sorry. I know that’s the antithesis of self-care and the mental health narrative. And, yes, you should get to enjoy yourself. But also: You can do something. And so, I’m doing stuff, along with making these stupid Instagram videos. And I know people watch those Instagram videos, but I’m also gonna fully come out of this thing with a pilot. When I try to sell it, people are gonna go, like, ‘Cool, I guess?’ Then I’ll go, ‘All right. Thank you so much.’ And that’ll probably be it. That’ll be the end of it. But I’m still gonna do it.”