It’s Always the Perfect Time to Watch Living Single

Living Single Photo: Warner Bros.

Looking for some quality comedy entertainment to check out? Who better to turn to for under-the-radar comedy recommendations than comedians? In our recurring series Underratedwe chat with writers and performers from the comedy world about an unsung comedy moment of their choosing that they think deserves more praise.

Although COVID-19 has postponed the HBO Max reunion indefinitely, Friends is truly a franchise that won’t die. The Thanksgiving episodes made their theatrical debut last year, and every time a cast member joins Instagram it’s a royal wedding–level PR event. But, as David Schwimmer recently had to be reminded, there was a Friends before Friends. It was called Living Single. For five seasons on Fox, Queen Latifah & Co. lived, loved, and laughed in Brooklyn. In the series, three roommates live in the same building as three of their friends. They cope with the work-life balance in the go-go ’90s and all wind up dating each other. And the opening credits are iconic. Sound familiar?

Since its streaming debut on Hulu, a whole new audience has been turned on to Synclaire’s cluelessness and Kyle’s fashions. But comedian and Black Monday writer Yassir Lester was there from the jump. Lester recently spoke with Vulture about how Living Single taught him at a young age that adults are people, too, the limits of how much you can learn from issue-based comedy, and what hypebeasts owe to Kyle Barker.

What do you love about Living Single?
The show was definitely on when I was a young man — a very young man, probably like 11. At the time I, my brother, my sister, and my mom lived with two of my aunts, Angie and Adele, and their kids also. So we lived in this weird, broke version of Living Single: the same thing with more kids and way less money. So it’s always been this weird association in my life. You kind of think of your mom and aunts and all these adults as monolithic. Living Single was the first thing that made me think, Oh, these are fully formed people who still want to have fun. Uncle Phil and Aunt Viv on Fresh Prince were phenomenal, but they were adult adults, you know? Whereas Living Single was like, I could probably end up a Kyle. And my mom and aunts are probably more like these women than I want to believe.

This show really centers the four women. Do you think that helped you understand that women have, like, interior lives?
Oh, absolutely — for (a) adults, but (b) black women specifically. Do you remember being young, and you’re watching something with your parents, and they start laughing really hard, and you’re like, What the fuck are they laughing at? What just happened? Because I don’t get it, because I’m stupid. Living Single was that. All the adult women in the room were always laughing. I would laugh when Overton’s hat fell off or something. But it felt like one of those things that was made for them, you know? And because of that, it made me realize, Oh, these are just girls who became women, and those women had kids. But they still want to go to a club, or go on a trip, or meet a guy. Whereas when you’re a kid, you’re like, They’re my mom. They want to feed me and love me and tell me I’m the best.

When you chose this show to talk about, you specifically mentioned this show being underrated compared to Friends.
I think at this point, so many deep dives have been done, and it’s very clearly stated on the record that the head of NBC at the time said he wished he would have gotten Living Single, and Friends was the retaliation to that show.

But Living Single dealt with [bigger issues]. For one thing, I’m black, so it’s going to resonate more. It felt like Brooklyn; it felt like Queen Latifah. I was in love with Kim Fields. But on top of all that, it felt real. On Friends, even though they had different jobs, they all felt like they were the same income level. To me, Living Single lived their archetypes a little bit more. Overton felt like a handyman, whereas Kyle felt more like a … whatever Kyle was.

Yeah, what was Kyle’s job? Wearing vests?
I think he was an accountant or consultant. He wasn’t a lawyer, because Maxine was the lawyer. Khadijah had the magazine, and Synclaire worked there. Regine was at the boutique.

She was a buyer.
Which is a job Rachel eventually got on Friends just saying. But in terms of character … You know when someone is doing a Chandler impression, regardless of whether you watched the show or not. And that speaks volumes. They did characters where I think Living Single did people. Does that make sense?

It wasn’t just the characters on the show. The way they dressed, their job, the way they talked — it was fully defined. It wasn’t just a few quips to make you think, She’s a real dum-dum! It showed the spectrum of black femininity and the spectrum of the black experience. It wasn’t a super-hood show. They weren’t ever in a position to make fun of the characters because of where they live or what they did. Whatever joke you got came from the actual character.

I also noticed that very few episodes were standard sitcom plots. Nobody got trapped in an elevator in the episodes I watched.

And the episodes you recommended straight up felt like you were pranking me. Part of me was like, There’s no way a network sitcom does a breast-reduction-surgery episode in the early 90s.
I know! That’s what I’m saying. That’s why this show was so dope. I don’t want to be one of those guys saying “You can’t say anything now! You can’t kiss a woman you don’t know!” or whatever it is those dudes complain about. But why hasn’t there been a weird breast-reduction episode of television in recent history? Or like the abortion episode on Maude? We just don’t do that anymore, unless it’s some weird FX show. But these were the main shows on TV dealing with that. I find it so interesting.

Living Single tried to tackle high-stakes issues using really big jokes, and a lot of prestige comedies today are incredibly low stakes with tiny jokes.
Right. I think so much of that comes from [the show creator] being a woman, being a black lady. If you’re any minority, if you’re a woman running a female-led show at that time, you have to come big. Because no one else is going to talk about it for you. Yes, there’s a certain level of sensitivity that we have now that we didn’t back then, but at the same time, this is the conversation, so let’s have the conversation. It took a level of bravery. That’s why it’s so rewatchable. Those jokes still work, and those ideas still resonate.

In the sexual-harassment episode, Khadijah makes a joke about how little accusations of harassment matter. She makes an Anita Hill joke and says that she could still get nominated for the Supreme Court. Uh-oh! Still relevant.
Yeah! I think we all, in our generation especially, think that we’re the only ones who ever fought the good fight and that we’re really taking things head-on. But there’s probably an episode of Mama’s Family that tackles racial injustice, you know? The Anita Hill thing, we think we’re the first ones to make that joke? No. We’re all aping our predecessors.

That’s a joke for women. That’s a joke for black women. That’s a joke heard by a public that, at the time, had done everything in its power to discredit Anita. And Fox was like, “Sure, we’ll air it.” That’s so cool.

We have to talk a little bit about the fashions.
Even that was part of their archetypes. Khadijah was always rocking a hockey jersey at home. In the office, a dope tweed blazer. Regine always looked like a Bloomingdale’s mannequin. Maxine was always ruler crisp.

In one of the episodes that I watched, Kyle was wearing a Michelangelo’s David necktie. Like, peeking through his vest.
That’s cool though! Kyle was weird because he had this voice. It’s almost like that thing where in cartoons, people with British accents or Indian accents are always geniuses. And they can be an idiot and be from somewhere else. They do the same thing with Kyle: He talks like that, and therefore he’s cultured and would wear that necktie. They would also just put him in a beret sometimes. What?!

In the breast-reduction episode, during the nice moment between him and Regine, he’s wearing a huge turtleneck, a necklace, and a scarf. There’s just so much shit on his neck.
[Laughs.] It’s such an iconic look. And we just let it fall by the wayside! I’m in L.A., and if you go up and down Fairfax now, there’s a bunch of people dressed like Kyle. And no one gives him his due. That look should be called “the Kyle.”

That episode was made for its audience, specifically. Here’s what it’s like to be a woman in America. The idea of an episode of TV being devoted to a woman getting breast-reduction surgery and dealing with her perceived value in society? That is a very deep cut for a show that’s like, “Also, watch The Simpsons next.” I don’t know if you’re a Friends fanatic but …

Oh, I’m in way too deep.
So what’s your breast-reduction episode of Friends? What made you go, Oh, that’s an oddly sociopolitical message to have in this sitcom?

There isn’t one.
Exactly. Exactly! Anyway, I just wanted to get that out there. And now I have.

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It’s Always the Perfect Time to Watch Living Single