Pop culture obsessives writing for the pop culture obsessed.
Pop culture obsessives writing for the pop culture obsessed.

10 essential episodes of Living Single you should check-check-check out

To talk about Living Single is to talk about two separate legacies: the one the series ultimately earned, and the one it deserved. That’s not to say that its immovable place in pop culture is unfavorable by any stretch: Created by Yvette Lee Bowser, the half-hour buddy comedy following six young, Black professional Brooklynites garnered a number of NAACP Image Awards, two Emmy nominations, critical acclaim, and a sustaining spot among the top five Black sitcoms of its era. For primarily Black audiences, Fox’s five-season 1990s hit was a microcosm of a culture that felt familiar, deeply relatable, and unburdened by dated stereotypes.

For then-27-year-old Lee Bowser, the premise was rather simple: She wanted to build a show inspired by her personal stories about dating and thriving in the big city. After Bowser wrote for A Different World and Hanging With Mr. Cooper, Warner Bros. introduced the young writer to hip-hop artist Queen Latifah and In Living Color alum Kim Coles, both of whom had active talent-holding deals with the company. The three shared a common frustration working for shows crafted by all-white creatives (Latifah and Coles each had a failed pilot under their respective belts) and wanted to helm a show fueled largely by their lived experiences. As the project began to take serious shape, Bowser and Warner Bros. surrounded the two leading actresses with family sitcom veterans Kim Fields (Facts Of Life) and Erika Alexander (The Cosby Show) to ensure the show’s success. Between Coles’ comedy chops, Latifah’s industry following, and Fields’ and Alexander’s unquestionable records, Bowser had fashioned a powerful cast of cultural staples for the brand new, soon-to-be-Fox-classic My Girls. The show’s title, of course, would be changed to Living Single before the pilot’s premiere.

From 1993 to 1998, viewers were invited to kick off their shoes and hang with a group of friends who were “true blue and tight like glue.” Khadijah James (Latifah) was the grounded, unflinchingly honest owner of a grassroots urban culture magazine called Flavor, which often took precedence over her personal life. Fortunately for her, she lived with two roommates who helped her strike a (barely) functioning work-home balance: cousin Synclaire James (Coles), an idiosyncratic aspiring actress and troll doll connoisseur; and Regine Hunter (Fields), a childhood friend and boutique buyer with perpetually upscale taste. Across the street lived Maxine Shaw (Alexander), the razor-tongued attorney and free-loading best friend. Rounding out their faithful group were upstairs neighbors Kyle Barker (Terrence C. Carson) and Overton Wakefield Jones (John Henton), a syrupy-voiced Wall Street accountant and folksy handyman, respectively.

The series showcased Blackness as it truly was: A vast amalgam of different identities, values, experiences, and ideologies. It was, without question, a Black sitcom that centered the lives of Black women and the different ways they navigated love and their environment daily. At its core, however, the series featured stories so damn funny they could connect with anyone. Who hasn’t dealt with the confusing business of developing romantic feelings for a friend? Who hasn’t survived questionable dates, met a partner’s family and friends for the first time, or struggled to find common ground with their parents?

That familiarity should have secured the same enduring, ubiquitous presence that we’ve witnessed with similar comedy mainstays like Friends, which premiered in 1994 on NBC. Once the newest juggernaut reached audiences, media critics couldn’t help but compare the two, with many employing a revisionist tone by insinuating that Living Single was the “Black Friends” despite the fact that the latter premiered over a year after the former. In a network landscape that held plenty of room for both shows to coexist peacefully, Friends and Living Single were made to compete for the same time slot, placing them in direct competition with one another. Regardless of a whip-smart script, consistent ratings, and an ensemble that was at the top of its game, the show never received financing, advertising, or awards season recognition comparable to its NBC counterpart, and was abruptly canceled in the middle of the fifth season. In the decades since the final episode aired, Lee Bowser and the cast have been outspoken about the show’s treatment by white executives and critics as well as the continued comparisons to Friends, though some maintain that they enjoyed the NBC show alongside everyone else.

Despite its position on a notably uneven playing field, Living Single has joined the ranks of classic comedies thanks to syndication, a streaming home with Hulu, and a vocal fan base that continues to advocate for the six friends in the coolest brownstone in Prospect Park. Though the last episode faded to black over 22 years ago, the exploits of Khadijah James et. al remain relevant, poignant, and as clever as the day they first graced television screens across the nation. Your time would be equally well-spent with any combination of the 118 episodes, but we’ve painstakingly selected 10 that we feel are most essential to the show’s identity.


“Great Expectations” (season one, episode six)

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Screenshot: Hulu

More often than not, a series can take some time to find its rhythm. Though Living Single connected with audiences almost instantaneously, it was its sixth episode, “Great Expectations,” that really nailed down both Lee Bowser’s original vision and the close-knit dynamic between this group of characters. The gang’s foray to a local night club became an early character study in how they would navigate life and dating throughout the show’s life with Regine attempting to dominate the spotlight, Kyle trying to socially climb his way into the popular establishment, Synclaire and Overtone sticking together in their own quirky fashion, Max attracting all the wrong men, and Khadijah remaining calm and controlled, awaiting the ideal target. The episode allowed each cast member to flex their comedic muscles and cemented just why they were the sitcom ensemble to watch. It was also the first instance of the cast members getting to flex their immense musical talents with Latifah performing Gloria Gaynor’s “I Will Survive.”


“Love Thy Neighbor” (season one, episode 18)
“Mystery Date” (season one, episode 19)

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Screenshot: Hulu

“Love Thy Neighbor” and “Mystery Date” was a two-part event and a necessary double feature. The former featured an important milestone for Synclaire and Overton’s relationship: their decision to finally address their comically obvious attraction to one another. When Overton goes on a date with happy-go-lucky Summer (Cree Summer), Synclaire sadly recognizes that her window of opportunity with the affectionate handyman was rapidly closing and decides to confront him once and for all. With a very official kiss (because we don’t really count their mistletoe-adorned smooch in “Living Kringle”; that was just a holiday tradition), one of television’s most wholesome, stable couples would take effect at last. A devastatingly handsome new neighbor named Hamilton Brown (Morris Chestnut) arrived just before the close of the episode, igniting a competition for his attention among the remaining women. When the episode aired in February 1994, the audience was given the chance to determine which woman would win Hamilton’s heart by voting through a hotline. Audiences handed the victory to Khadijah—a win for down-to-earth tomboys everywhere. Well, maybe “win” is a strong word here: The date was ultimately a bust, and Khadijah was sure to lay the blame squarely on the shoulders of the viewing audience. Still, the event stands as a fun exercise in fan engagement before the days of livetweeting.


“Five Card Stud” (season one, episode 23)

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Screenshot: Hulu

It would have been very easy to have the women expeditiously take down a foul-mouthed misogynist. “Five Card Stud,” however, rightfully placed the onus on Kyle to advocate for his friends when his boss, Lawrence (Bobby Hosea), called the women “bitches” during a friendly poker game. By the time the episode aired in 1994, Latifah’s Billboard-charting single “U.N.I.T.Y.”—which addressed this exact brand of disrespect—had already bloomed into her biggest hit to-date. (Naturally, the show was sure to air a portion of the music video during the episode’s closing credits.) While having Khadijah confront the offender would have been way too on-the-nose, making Kyle the one to hold a fellow man accountable highlighted Living Single’s mission to make the men of the show exemplify actual allyship. Besides, it’s always reassuring to see strong, Black women still get the protection they deserve, even if they are totally capable of defending themselves. Because why should they always have to?


“A Hair-Razing Experience” (season two, episode 13)

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Screenshot: Hulu

Living Single’s widespread relatability may have been a favored selling point; however, the show’s culturally specific episodes set the series apart from the rest by finding comical ways to contextualize serious issues within the Black community. Gun control, crime, sexism, and capitalism were just a few of the hills that Lee Bowser chose to conquer throughout five seasons, but season two’s “A Hair-Razing Experiment” spoke to the inherent politics surrounding Black hair—a topic that is still incredibly relevant. Kyle’s struggle to choose between workplace assimilation and his locks after being told that his hair has stalled a potential promotion continues to mirror the crossroads that many Black professionals face today, despite the greater prevalence of natural hair styles. Though Kyle is somewhat beholden to his unique hair, the two-sided conversation that precedes his decision is nuanced, intelligent, and somehow enhanced—not downplayed—by Regine’s hilarious preponderance of wigs for him to try.


“Singing The Blues” (season two, episode 15)

They bickered. They sniped. They ruthlessly tore each other asunder. The contentious air between sworn frenemies Max and Kyle was a source of countless laughs and the show’s wittiest material. It was also a totally transparent front. Despite their proclivity to throw barbs at one another, Max and Kyle harbored a chemistry that was difficult to define or ignore, resulting in a tequila-fueled hookup in the first season finale. Though they chose to remain friends, the door remained cracked for a future romance. Kyle’s sultry, pointed open mic performance of “My Funny Valentine” revealed lingering romantic tension between the pair and showed Carson’s range of talents. It is one of the show’s most noteworthy scenes, and a moment that would forever shift the dynamic between two sort-of enemies. And with a voice like this, is it any wonder how Carson would go on to become one of the most sought-after voice actors in gaming and nerd culture, with roles like Mace Windu in Star Wars: The Clone Wars and Kratos in God Of War?


“Baby I’m Back… Again” (season three, episode nine)

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Screenshot: Hulu

Though fans spent five seasons watching Khadijah entertain some of Brooklyn’s premier bachelors, none of her potential suitors held a candle to Terrence “Scooter” Williams (Cress Williams), her childhood close friend-turned-occasional boyfriend. His career in the music industry carried him all over the world, which complicated their relationship tremendously. However, the few moments they shared together emitted waves of undeniable chemistry that made viewers root for their (eventual) happy ending. It became impossible to maintain a steady bond despite every honest effort, including an impromptu proposal involving a squabble and a boomerang. They were absolutely soulmates, but even the strongest affection can’t overrule shitty timing. Their ever-fluctuating relationship personified the concept of loving something enough to set it free, and the ghost of their false starts would hover over Khadijah’s love life until the very end of the series.


“Shrink To Fit” (season three, episode 19)

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Screenshot: Hulu

“Shrink To Fit” not only brought a welcome guest appearance by Jasmine Guy, but also stoked a conversation about mental health. Between a newly competing magazine, financial woes, and the sight of Scooter moving on romantically, the last remaining threads of Khadijah’s sanity were beginning to snap. Watching her literally and figuratively handle her business while serving as an emotional rock for others could be tiresome at times, so seeing the overworked magazine editor finally succumb to the pressures of maintaining her strong image wasn’t pretty, but it was a necessary turning point. Undoubtedly borrowed wig askew and emotions on high, Khadijah reminded audiences that even the most iron-willed characters still had room for personal growth, and that the strongest among us need substantial care. The episode also doubled as a reunion of sorts between Guy and Lee Bowser, who wrote exclusively for Guy’s top-tier character Whitley Gilbert during their A Different World days.


“A Raze In Harlem” (season three, episode 21)

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Screenshot: Hulu

In its third solid season, fans began to see the Fox hit take risks with its formatting and storytelling. When Kyle took up a cause to save an old jazz club from demolition, it wasn’t enough to watch the gang to protest City Hall. Instead, “A Raze In Harlem” turned into an elongated dream sequence where each character took on a Prohibition-era alter ego during the ill-fated Showboat Club’s heyday. The episode spared no glamour as it payed fitting tribute to the Harlem Renaissance. Never ones to begrudge their resident vocalists a chance to serenade their audience, Lee Bowser and the writers let Carson and Latifah sing while the entire cast got the chance to play exaggerated characters that were a departure from the ones that typically guided the series. Come for Carson’s velvety rendition of “Honeysuckle Rose,” stay for the breathtaking, sepia-toned final shot of modern-day Kyle walking through 1920s Harlem.


“Back In The Day” (season four, episode 15)

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Screenshot: Hulu

By the fourth season, faithful fans had come to adopt this vibrant group of friends as their own, committing threads of individual stories to memory over the course of 95 episodes. “Back In The Day” showed audiences something they hadn’t seen from the friends before: the day that Synclaire moved in and completed their circle. As the women traveled into the city to watch Khadijah accept a prestigious journalism award, they reminisced about a time when Max was an actual roommate and law student, Regine and an afro-wearing Kyle were dating, and Khadijah delivered pizzas to raise money for her big business venture. Overton was the only tenant who even resembled the older, more settled version we’d come to know over the years, while the rest were still in the throes of pursuing their dreams. More than anything, the episode is a testament to how deep the roots of their friendships reach: Max literally threw Regine through a banister and their relationship somehow survived. Let no amount of bickering convince you that these women aren’t sisters for life.


“Never Can Say Goodbye” (season 4, episode 24)

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Screenshot: Hulu

Though the series would continue for another 13 episodes, the season four finale marked the end of an era for this Brooklyn brownstone. Synclaire and Overton’s kismet coupling was sealed with an intimate wedding, and suddenly the show was no longer about young singles figuring out how to mingle, but about young adults preparing for the next stage of their lives. Kyle accepted a position that would require him to relocate to London, Max had to decide whether or not she would tag along at his request, and Khadijah and Regine were left to adjust to life without Synclaire as a constant presence (even though the newlyweds would move into a new apartment in the same building). Though new roommate Tripp (Mel Jackson) would try to fill the voids left by both Synclaire and Carson’s real-life departure from the show, it was impossible to replicate the energy harnessed by the original cast. The shortened final season had a few gems of its own, but “Never Can Say Goodbye” could have easily doubled as a fitting series finale.


Honorable Mention

“He Works Hard For The Money” (season three, episode eight)

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Screenshot: Hulu

Any conversation about Living Single wouldn’t be complete without mentioning its roster of legendary guest stars. Flip Wilson, Antonio Fargas, Heavy D, Grant Hill, Gladys Knight, and Naughty By Nature were just a few of major celebrities that graced the Fox lot. But when Hollywood luminary Eartha Kitt dropped by to play a purring, hopelessly seductive industry icon, nobody else could compare. A scene stealer and a damn delight, “He Works Hard For The Money” is a lovely reminder of Kitt’s larger-than-life pop culture presence. Some other star-studded episodes include “Like Father, Like Son,” “Crappy Birthday,” “Do You Take This Man’s Wallet?”, and “One Degree Of Separation.” If you squint, you may even catch up-and-coming comic Will Ferrell in season two’s “Talk Showdown.”

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