Black Monday’s Yassir Lester Finds Comedic Inspiration in Bugs Bunny and Wes Anderson

You’re probably already familiar with Yassir Lester’s humor whether you realize it or not. Maybe you’ve seen one of his hilarious tweets, or watched him get baited by Ziwe, or even recognized his voice in animated series such as Duncanville, in which he plays a trendsetting teen influencer flush with free stuff. Off-screen, though, he’s written for some of the most critically acclaimed (and at times controversial) comedies of the last decade: Girls, The Carmichael Show, and most recently, the Showtime ‘80s stock market comedy Black Monday, in which he stars alongside Don Cheadle, Casey Wilson, Andrew Rannells, and Regina Hall.

Next, his work will be seen on the forthcoming Apple TV+ comedy series from Alan Yang and Matt Hubbard, starring Maya Rudolph and Mj Rodriguez. Until then, though, Lester—who cites influences ranging from “Bugs Bunny if Elmer Fudd hit him in the back of the head with a shotgun,” Happy Endings’ Damon Wayans, Jr. and Adam Pally, and the Tina Fey extended universe—spoke to W for a Culture Diet interview. Below, he discusses his comedy inspirations, reveals the multiple books he’s got cracked open at the moment, and reveals his ambitions to write and illustrate a book of his own.

You play a stockbroker, also named Yassir, on Black Monday. What is the origin story of that character? Were you always supposed to have the same name?

I started on Black Monday as a consultant when it was a pilot, before it had even been filmed. They had to write a few extra episodes when Showtime thought it was good. In the pilot there was an Indian character, and the creators were like, “Why don’t you do it? It’s a small guest spot.” I was on a show called Making History at the time, and knew it was getting canceled, but I couldn’t take any other full-time roles. So I told them, “Sure, if it’s just one or two lines. But I can’t be an Indian dude.” And though I don’t know him, my dad is Palestinian, and my name is already Yassir, so I kind of could look like Yasser Arafat.

You’ve worked in comedy for many years—performing stand up, writing and appearing on television shows like Girls and The Carmichael Show. Growing up, was there a moment where you realized you were funny enough to turn comedy into a career?

Growing up, it was the typical stuff—using comedy and humor as a means of deflecting. But I was also, and still am, into visual artistic endeavors. My dreams growing up were to either be a comic book artist or do comedy. I wrestled with those, but I never saw myself progressing enough as an artist. I probably could have tried harder, but being funny and writing funny things and performing always got to me more. Chris Rock’s Bigger & Blacker came out in 1999, and that was the first time I thought I actually wanted to do it.

What other shows or movies were formative for you?

The Fresh Prince, Martin, and Living Single. Goofy, weird things shaped and formed me, like Don't Be a Menace to South Central While Drinking Your Juice in the Hood, Austin Powers, Scary Movie, Ace Ventura. I knew I could do that if I stopped eating, used all my money for gas to drive around and do open mics, and pick it up from there. A giant influence was The Royal Tenenbaums. I know people would say Rushmore and I love that film, but The Royal Tenenbaums made me realize you could be an artist and also be hilarious.

Do you still have an interest in the visual arts? Do you read a lot of comics?

Oh, yeah! It’s so sad as an adult man to be like, “Absolutely!” But I’m also trying to write my first book right now, and it’s not a comic book, but it’s a hybrid of my visual arts interests. Over the course of the pandemic, I really wanted to refine my skills and learn to oil paint. I bought a book, read it, and started practicing. Shockingly, it turned out alright. [Laughs.] As an illustrator, I’m not phenomenal but I’m very good. With books, especially for comedians, it’s easy to present a series of funny anecdotes—but I wanted to be like, “If this book tanks, what’s the best way for it to entertain me? If I see it on my shelf and it’s attached to so much pain and suffering because it’s a flop, why would I still like it?” I’d have to involve all of the things that truly mean a lot to me. This is pretentious, and I want to apologize for that, but I want it to be the totality of me. I also figure, if people read it and they don’t like the words, they might like the pictures. And if they don’t like the pictures, they might like the words. And if they don’t like both, they are probably one of my teachers from high school.

What other books are on your bedside table right now?

Speaking of a comedy memoir that stands out from the pack: Casey Wilson’s The Wreckage of My Presence. She’s so funny and so real. Stylistically, the way it’s set up doesn’t feel typical. It actually feels like her. I’m also reading a book called The Case Against Reality by Donald Hoffman. It’s about how, as humans, what we think we see as reality is really just what we need to see for survival. The world, to us, looks completely different than it does to a spider. They need a certain set of fitness to navigate the world differently than we do. There’s also a comic book writer named Tini Howard and everything she does is phenomenal. I’m currently reading her run of this Marvel comic called Death’s Head. I also started reading The Three-Body Problem by Liu Cixin.

Who are some of your favorite artists to follow on social media?

Josh Mecouch, he’s an artist who I love on Instagram. His username is @pantspants. He did a weird motivational book of illustrations called Conquer the Day. He does these funny illustrations, it’s a fake book of affirmations.

You’ve gone viral a handful of times on social media. How has your relationship to a platform like Twitter evolved over the years, especially since you’re a comedian who uses it as a space to share jokes?

It’s hard. I don’t want to come off as someone who’s like, “The internet is killing comedy, man! You can’t say nothing no more!” But also, there is a level of anger that everyone is constantly at, and I am not someone who lives to make people mad. At the end of the day, I just want people to laugh and I mean that sincerely. People are going to be mad just to be mad and it is what it is, but there are also people who want to say whatever they can to make those people mad. Why are we doing that? I know my intentions and the things I think are funny. I’ve never been a fan of comedians you see on stage who are like, “Hey, here’s a reference for four people,” and only four people will laugh hard at a joke about some obscure band or movie that no one’s ever heard of. The whole point of me getting into this is that I have some ideas I think are funny to me, but also to more people. The internet can be great for that, and other times it can go the opposite way. We also have more access to information and news stories than ever before, and sometimes there’s just not a good time for a joke when the cops are killing people every day, and the Palestine and Israel conflict is going to be on fire. And I don’t mind if I have to apologize for a joke and take the L.

You host a podcast with your brother called My Brother’s Sneaker. What other podcasts do you listen to?

I’m not really a podcast person. Someone has to knock my door down to get me to listen to one. Otherwise, I’ve just gotten older so I listen to a lot of slow, relaxing oldies. A lot of soul music. My girlfriend Chelsea Devantez has a podcast called Celebrity Book Club and that’s doing well. It makes me feel like I need to see what else is out there because my podcast is just for fun. We’re not trying to become Serial. Here’s a deep cut—ever heard of The Daily? Or Radiolab? [Laughs.] My friends also do one called Black People Love Paramore, and it’s about all of the things that Black people love but might be shamed for loving.

You mentioned loving oldies. What is the last song you’ve had on repeat?

“Come and Get Your Love” by Redbone has really been hitting in very good way as of late.

What’s the last concert you went to?

For the most part I’m not too huge on concerts, but when Kanye did the Saint Pablo tour, I saw that three times. I enjoy them when I’m there. I did see Young Thug with Machine Gun Kelly at the Palladium in L.A. with my brother and Rell Battle, another phenomenal comedian.

Do you remember the last movie you saw in theaters?

The Harley Quinn movie, Birds of Prey. It was either that or Bad Boys for Life. By the way, Birds of Prey was a banger. I think it would have been seen by more people if it weren’t for theaters shutting down because of Covid.

What’s the last thing you Googled on your phone?

It was actually a DC Comics thing. I was trying to send a meme to someone because I was saying that the people who wanted to see Elon Musk on SNL are the same people who wear shirts with a picture of the Joker on it that says “You’re laughing because I’m different, I’m laughing because you’re all the same.” Have you ever seen that? Telling another human adult feels more pitiful and less funny than I thought it was before.

Are you into astrology at all?

I know my sign, and I know that Carl Jung said that you can’t properly diagnose anyone as a psychologist or psychotherapist without knowing their astrology chart. Those are the two most interesting things about it to me. Now, I say to me very specifically because any belief system is equally as beautiful or ridiculous as the next one, as long as they do not cause harm to the people involved or people around it.