role play

Hassan Johnson Is Television’s Funniest Gangster

Photo-Illustration: Showtime/HBO Max/Hulu

As Roland “Wee-Bey” Brice on The Wire, the character he’s best known for playing, Hassan Johnson is the true embodiment of the expression “ride or die.” As the most loyal member of Avon Barksdale’s criminal enterprise, he scraps, kills, and ultimately goes to jail for life to ensure the greater good of the operation. It’s this unflinching commitment and self-seriousness that make him an unlikely source of comic relief throughout the series. In one famous interrogation scene from season one, he nonchalantly takes the rap for multiple murders committed by fellow gang members, demanding nothing in exchange from the police but a “pit sandwich and some potato salad.” On several occasions, his hardened persona is juxtaposed against his unlikely love for tropical fish. He’s even become the source of an iconic reaction meme used online to signify bewilderment, shock, and confusion.

The comedic elements of Wee-Bey’s persona have served as a blueprint for a number of the roles Johnson has played since. Beginning with a 2006 guest stint playing a Suge Knight–like figure on Entourage, Johnson has animated several variations of drug dealers and gangsters for comic effect. He popped up as a whimsical drug dealer in the 2015 movie Staten Island Summer, where he acted alongside SNL veterans like Colin Jost, Cecily Strong, and Fred Armisen. He currently plays Drew on Showtime’s Flatbush Misdemeanors, a multidimensional hustler who constantly torments the show’s protagonists Kevin and Dan. Most recently, he made an appearance in the second episode of Hulu’s This Fool, playing an aging gangster who tries to rally his gang to rekindle an old beef but is only able to marshal his elderly, confused grandfather. Johnson has played against type in comedies too, most notably in Chris Rock’s 2014 movie Top Five and Tracy Morgan’s TBS show The Last O.G. But his comedic niche is that of the gangster who pivots between being terrifying and baffling from line to line, and who delivers deeply silly lines with the untouchable swagger of someone whom no one in their life dares to question.

Johnson recently spoke about his famous meme, the difference between playing a gangster in a comedic and dramatic context, and how he feels about being typecast in these roles.

How far back did you know you wanted to work in comedy?
I always knew I wanted to be on television. But as a child, coming from where I came from — I grew up in the ’80s — my first introduction to comedy was Eddie Murphy. When I saw Delirious — it was probably Delirious, but Raw put the nail in the coffin — I wanted to be like Eddie Murphy. Not to mention, when I was a kid, people said I resembled Eddie Murphy. Mainly when I was outside of New York City, for some reason. But that helped, too.

How did that interest in comedy manifest when you first got into the industry?
In the beginning, I didn’t know how to navigate through that, or to that destination. So the spark was comedy, but then it was more like, However I can get on television, I’ll just get on television. Then the opportunity came and I went to an open-audition call for Clockers, and the rest is history. Now, through manifestation, always thinking positive, and just saying that I wanted to start doing more lighthearted things, it’s been happening.

I think there were glimpses early on in your output that comedy was an interest of yours. Do you ever think of Wee-Bey from The Wire as being a comedic character?
I actually do. A buddy of mine has said that you could drop Wee-Bey into different scenarios. Someone put up a meme on Instagram. It had a Saint Laurent logo on it, and then the caption says, “The shoes that Wee-Bey wears to do murders.” I’m just like, Well, he ain’t a fashionista, but that might play into a whole other segue for his character. Like, he’s going shopping, he’s in the men’s shoe department at Neiman Marcus, and he’s buying shoes just to go and get them dirty.

It’s funny you mention Wee-Bey memes, because there is that famous one of him reacting to the news that he and Little Man shot an undercover cop. Do you hate talking about the meme at this point?
No, because The Wire has a life of its own all over again. It’s been off the air longer than it was on the air. It doesn’t get old. I guess I have an out-of-body experience to be able to see that and understand that. Subconsciously, if I was annoyed by it, that’s what undoes that. It’s so clutch. People use it for every little thing, and it’s right on point.

I actually see Wee-Bey as the model for a lot of the comedic work you do now. I was rewatching the scene in season one where he’s being interrogated by the police, and he’s bargaining murder confessions for a helping of potato salad. It doesn’t play like a scene of a person throwing their life away, it plays funny.
It actually is! Except when we shot that with David Simon, it was 6 a.m. — probably one of the earliest call times I’ve ever had. So I don’t know if any of us even adhered to the comedic undertone of it. But I think the fact that we played it so straight and nonchalant, it resonates even more. Someone just posted that on Twitter. It was like, “Wee-Bey had to be the most laid-back and nonchalant serial killer.”

You played a similar drug-dealer character in Staten Island Summer. Between all the SNL cast members in that and your role in Chris Rock’s Top Five, you’ve shared scenes with a lot of comedic powerhouses. What have you learned from those experiences about your approach to comedy?
For one, I learned that I might actually be funny. If you think about it, from Staten Island Summer to Top Five, that’s all SNL alumni in one way or another, so that kind of makes me feel like I have honorary status from SNL. I’ll take what I can get. I think it was around Top Five that I thought, Oh yeah, you can do this now. You can pull your weight. 

How do you approach it differently when you play a gangster or a drug dealer in a comedic context as opposed to a dramatic role?
I always wanted to get into comedy, because I think when it’s funny, it’s more fulfilling and elating to your soul and your spirit. The gangster stuff is hard. I’ve always said Wesley Snipes as Nino Brown in New Jack City, and Larenz Tate as O-Dog in Menace II Society — those were the hardest roles to play. Bar none. Oscar-worthy. They were such quintessential drug dealers and products of their environment. They were so scary.

It’s especially hard when you’re not like these people. I mean, I’m not a serial killer. I’ve never shot a gun in my life well, I’ve been to a range but I’ve never shot a gun at anyone to hurt them or anything like that. To be able to do that, you have to go to a really dark place. And then you don’t want to overcompensate, because you have to be believable. It’s delicate. There’s a fear factor in there too. Even in comedy, you have to get that across, and if you’re not communicating that, it’s gonna be like you’re trying to be funny, and you’re gonna miss the mark. It could all fall apart, like paper when it gets wet. It’s almost like when we film chase scenes and the camera guys and the DP tell us to run half-speed because it’s going to look like we’re going full speed.

Drew in Flatbush Misdemeanors is the first chance you’ve had to really sit in a comedic character over a long period of time. What was the genesis of that? How did you feel about the opportunity going in?
When I first got the audition and the breakdown, I was like, See, I like this. First of all, it has the most famous borough in the world in the title, Flatbush. That alone got the hairs on my neck growing. Then I saw “Misdemeanors,” and thought, What could this possibly be about? My agent sent me a link to the YouTube web series that some people were familiar with, but a lot of people weren’t. I watched maybe three or four episodes, and I said, “Oh, this is smart. This is smarter than I was expecting it to be. I want to be a part of this.”

But I didn’t want to do anything conventionally. I told them, “I don’t want to make an audition tape.” It was in the middle of COVID, and that was all you could really do at the time. But I’m an old-school guy. I love to be in the room with the casting directors and everyone, because that’s when they really get to see who you are and feel you. I said, “I don’t want to do the audition tape because they’re not going to understand what I could bring to the table for this character through a few lines. They really need to talk to me. They need to know who I am, and see whatever parallel universes Hassan and Drew are residing in.” And that’s what happened. My agent set up a Zoom with Kevin and Dan, and a couple of other producers at Avalon and Showtime, and we just kind of hashed it out for 30 minutes. They were like, “Yeah, you’re in. You totally get this. Let’s do this.” I think it was the perfect match.

There’s a parallel between your character in the second season of Flatbush Misdemeanors the character you play during your appearance on This Fool. Both of these guys are older men, realizing that it’s unsustainable to continue living the street life as they age.
You can see the prequel to that. We all know that, with this street life, there’s only two places you end up: dead or in jail. No one ever wants to be at the end of an “I told you so.” A lot of us dodge those bullets, and that’s when you have to laugh and just say, “Phew, that was a close one.” I think, with these characters, it’s not sustainable anymore. They think, I wasted so much time and so many years throwing my potential away. Now I realize what I could do with myself, but I have less time ahead of me than I did before. That’s where the revelation comes in with certain people. And then, if you knew them from 20 years ago, you’ll say, “Wow, that’s not the same guy as before.”

They made you wear a Lakers jersey on This Fool. As a well-documented Knicks fan, I figured that must’ve been tough for you.
I know, right? That was a setup. That was a big-time setup. But I wore it with good grace, for all intents and purposes.

You’ve done a few comedic roles that don’t fit the mold of the ones we’ve been talking about. In Top Five and The Last O.G., your characters aren’t gangsters at all. In the future, are you looking forward to not being typecast and playing gentler characters?
I would agree with the idea that I was typecast up until these latest projects — starting with Top Five, leading up to The Last O.G., This Fool, and also playing Drew on Flatbush. I think that, in itself, is the break from the norm that is relinquishing me from the typecast. It’s in a realm that we’re familiar with, but we’re just not used to seeing me do. Now, we have to see where the manifestation and the metamorphosis takes me. I’m even open to character comedic acting, like The Klumps. I’m ready to dress up and put makeup on and really transform into someone else. I’ve done some revamping, and I’m excited to see where it takes me.

Hassan Johnson Is Television’s Funniest Gangster