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The 11 Most Essential Episodes of Living Single

Photo: Courtesy of Warner Bros

This piece was originally published in February 2018. We’re republishing it today for the 25th anniversary of Living Single’s premiere.

One of the most sincere pleasures I’ve had this year was rewatching Living Single shortly after Hulu made the entire series available in January. Running for five seasons beginning in 1993, Living Single centered on the professional and romantic lives of a group of friends living in Brooklyn: a hilarious, highly ambitious editor and magazine publisher Khadijah James (Queen Latifah, further cementing her ability to move through mediums with panache); Khadijah’s airheaded, sweet-natured cousin, Synclaire James (Kim Coles); the sharp-tongued, pugnacious attorney Maxine “Max” Shaw (Erika Alexander); the stylish, wig- and gossip-loving Regine Hunter (Kim Fields); the down-to-earth handyman Overton “Obie” Wakefield Jones (John Henton); and the exceedingly confident, finely dressed stockbroker Kyle Barker (T.C. Carson).

Before rewatching the series, I wondered if it would live up to my desires. Would I realize I was looking back on it through the lens of nostalgia? Thankfully, I quickly learned that Living Single remains amazing. The humor is sharp, the characters distinctive, the cast chemistry inviting, and the narratives the right balance between outlandish and poignant. Here are 11 of the best episodes of Living Single that exemplify why the show was one of the definitive ’90s sitcoms and continues to endure today.

“A Kiss Before Lying” (Season 1, Episode 4)

My favorite aspect of Living Single is the often venomous, lustful dynamic between Max and Kyle. They exemplify the idea that there is a thin line between love and hate. Max and Kyle’s tense relationship also grants Living Single its best physical humor, making it a crucial aspect to the heart of the series. “A Kiss Before Lying” has Max scrambling as her ex, Greg, who left her abruptly after five years because of her professional success, slinks back into her life with his fiancée in tow. Khadijah responds as any best friend would, encouraging Max to leave Greg in the past. Max has other ideas, though, setting up a dinner at Khadijah’s place and hilariously roping Kyle into pretending to be her man as a last-minute effort to flaunt a more perfect life than what she actually has. Erika Alexander and T.C. Carson are adept at physical humor, heightening the saccharine fake relationship and the silliness of this dynamic, making “A Kiss Before Lying” one of the most hilarious episodes in the series.

“Playing House” (Season 4, Episode 17)

The on-again, off-again relationship between Max and Kyle is undoubtedly the strongest relationship in Living Single, at least romantically speaking. (But I can understand arguments for the perfectly matched Overton and Synclaire, who stand out in episodes like “Never Can Say Goodbye,” or Regine’s own romantic history in episodes like “Do You Take This Man’s Wallet?” as she plans the wedding of an ex.) “Playing House” demonstrates just how drawn to each other these strong-willed people are, while balancing two strong story lines: Overton and Synclaire having the apartment to themselves when they try out living together, and Kyle using the cover of a trip to Japan to hook up with Max in a hotel. Regine knows something is up despite Max and Kyle continuing to pretend their relationship is currently on the back burner, adding a hilarious dimension to the episode.

“He Works Hard for the Money” (Season 3, Episode 8)

I loved Living Single as a kid, but one thing I forgot was just how many amazing cameos the series has. “He Works Hard for the Money” features one of my absolutely favorites: The marvelous, incomparable Eartha Kitt playing a famous actress named Jacqueline Richards, who is a new client at Kyle’s firm. In many ways, Kitt plays an outsize version of herself, poking fun at her own image as a grand, talented, lascivious diva. Kitt is hilarious as she purrs lines like, “Oh, the affairs this apartment has seen” and “I never do business without a drink” with aplomb. The dynamic between Kyle and Jacqueline is equal parts uproarious and tenderhearted as they develop a real friendship. Bonus points for the mention of Bette Davis and other classic Hollywood legends.

“Great Expectations” (Season 1, Episode 6)

Living Single is a series that finds its groove early on. Its strong voice, the distinctive quality of the characters, and its warm humor are all immediately apparent — that’s why it’s so hard to choose just 11 episodes. (If you’re looking for more, just binge seasons one through four. Trust me, it’s worth it!) But “Great Expectations” features a pop-culture trope that easily wins me over: a group of women getting dolled up together in the bathroom before a night out. Hijinks ensue, of course, once they get to the club. Max is saddled with a gold-toothed man who announces that he wants to “sop her up with a biscuit,” Khadijah proves to have high standards when it comes to her flirting partners,” Regine is pissed to learn that her one-of-a-kind dress is a popular look for many women in club, and Kyle strikes out despite his best efforts. It’s a fun, light episode that demonstrates the early strength of Living Single’s casting and comedic capabilities.

“I Love This Game” (Season 2, Episode 2)

Another strength of Living Single is its great athlete cameos. Typically, these sports appearances cross into Khadijah’s work life as the editor of Flavor. “I Love This Game” elaborates on her personal love of basketball, in which real-life WNBA legend Cheryl Miller plays an old rival of Khadijah from her hig- school years. Miller easily bests Khadijah when they decide to settle their long rivalry in a one-on-one game, but thankfully Khadijah leaves with her dignity intact, if not with the bragging rights. What I love about this episode is Khadijah’s competitive spirit: Along with Max, whom I connect more with as time goes on, Khadijah is one of the early examples of a fiercely ambitious black woman I witnessed in pop culture as a kid. Even when her competitive edge gets the best of her, I can’t help but be inspired by her dedication and zeal.

“A Hair-Razing Experience” (Season 2, Episode 13)

Conversations about hair and respectability politics have existed within the black community for decades. In this episode, Living Single questions ideas of authenticity and culture when Kyle is told by an upper-management figure that his hairstyle stands in the way of gaining a managerial position on an important account. That this boss is also a black man makes the criticism sting further. Kyle spends the rest of the episode considering if he’s willing to trade his hairstyling — an extension of just how proud he is of his blackness, and a representation in his interest in a certain brand of authenticity — for a move further up in the corporate echelon. Kyle, of course, stays true to himself despite the possible risks.

“What Next?” (Season 1, Episode 27)

It’s astounding to think that the first three seasons of Living Single each had 27 episodes, but what’s even more astounding is the show’s overall consistency. Season one builds to a great finale that pits Khadijah’s current paramour, Alonzo, with childhood friend and old flame Terrence “Scooter” Williams (Cress Williams, who is currently the lead of Black Lightning). Alonzo asks Khadijah to move in with him, but she has trepidation once Scooter returns to New York hoping to rekindle their romance. There are also great side plots, including Maxine’s frustration at work when she gets reprimanded for suggesting a wealthy, beautiful client get a prenup for her upcoming marriage. The episode ends on a stunning cliff-hanger: After a whole season of venomous insults and hilarious barbs, Max and Kyle drunkenly sleep together.

“There’s Got to Be a Morning After” (Season 2, Episode 1)

The season-two premiere has many pleasures: watching Khadijah and Scooter navigate their rekindled relationship, Synclaire’s dopey humor, Regine’s keen nose for gossip. But the highlight is seeing Max and Kyle’s reaction once they wake up in each other’s arms. Erika Alexander is a marvelous comedic actor. Watching the way her face contorts into a deep frown, and how every gesture communicates Max’s weird mix of lust and animosity toward Kyle is simply fun to watch. Honestly, I am putting this episode on the list for the melodious yet cutting manner Alexander says a single line once Max realizes the gravity of her situation: “Kyle, if I hear one word of this, I will kill you, burn you, and salt the earth where I bury you.” (This whole list could just be Max and Kyle–specific episodes. If you delight in watching these two spar as much as I do, I also recommend season two’s “Singing the Blues,” season four’s “Never Can Say Goodbye,” and season five’s “Love Doesn’t Live Here Anymore Part II.”)

“Doctor in the House” (Season 4, Episode 12)

I have always been interested in the ways black sitcoms handle class. Living Single doesn’t shy away from considering the multiplicity of the black experience and how it changes along lines of professional desires and class backgrounds: Consider Regine, whom Khadijah always reminds grew up in the projects but aims to wear the markers of wealth. “Doctor in the House” sees Khadijah join her anesthesiologist boyfriend, Charles, at a prestigious gathering where he’s receiving an award. But Khadijah bristles among the bougie black elite who look at her magazine Flavor as a cute side project and note how “ethnic” her name is. It gets worse from there, eventually putting a strain on her relationship with Charles. If for no other reason, I love this episode because it is situated in Khadijah’s arc about her desire for a partner and the importance her work has in her life.

“Mystery Date” (Season 1, Episode 19)

While Regine fancies herself as the best at pulling eligible men, it’s Khadijah who has the hottest men throughout the series — even catching the attention of various celebrities. In “Mystery Date,” Maxine, Regine, and Khadijah vie for the interest of a new neighbor in their brownstone played by Morris Chestnut. It’s Khadijah who comes out with a date, though he ends up not being as much of a catch as his good looks suggest. “Mystery Date” exemplifies how great Living Single is when it leans into arch, ridiculous humor that pits the very different yet equally strong personalities of the cast against each other. It’s brimming with great line deliveries and physical humor, and I’m especially fond of Queen Latifah’s fourth-wall-breaking performance. (If you’d like other blissfully ridiculous episodes, check out season one’s “Burglar in the House,” which shows Khadijah wielding nunchucks and “Not Quite Mr. Right” from season four.)

“Shrink to Fit” (Season 3, Episode 19)

Seeking psychiatric help for mental-health concerns remains a touchy concern within the black community, no matter where you’re from or your class background. “Shrink to Fit” represents the pop-culture perspective of this ongoing conversation. Khadijah has worn herself out, putting her strenuous career above her mental and physical health leading to a breakdown. She’s working a second job to keep Flavor afloat and she learns Scooter is seeing someone new, which sends her over the edge she was dangling from. She ends up reluctantly going to a psychiatrist played by A Different World alum Jasmine Guy.

Thankfully, the creatives behind Living Single aren’t afraid to lean into a bit of absurdity with this subject. Khadijah shows up for the appointment wearing shades and an obvious wig (probably swiped from Regine’s closet), dodging questions that touch the nerve of her own problems. “Psychotherapy doesn’t get much respect in our community,” Guy’s character notes. Living Single may only be 30 minutes and doesn’t return to this plotline, but its approach to the necessity of mental-health care in the black community proves to be potent. I also was deeply struck by how the episode considers the ways Khadijah puts everything before herself, to the point she doesn’t even fully enjoy the job she has poured so much effort into. “Shrink to Fit” exemplifies the continued impact of this series: great comedic acting, an ability to balance the farcical with the sincere, and a moving poignancy about the concerns of the audience it targeted that still resonate today.

The 11 Best Episodes of Living Single