By Sydney Scott ·
On this day 25 year ago, Living Single made its debut and provided a space on television for Black women to see themselves. An honest reflection of ambitious Black women working and living in Brooklyn, Living Single‘s Khadijah, Régine, Maxine, and Synclaire represented at least one woman in every Black girl’s squad.
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But one of our favorite parts of the show was its long list of actors, athletes, rappers and singers who’d stop by the ladies’ apartment; or show up in Overton and Kyle’s spot upstairs. The show also had a number of memorable guests, who provided plot twists and unforgettable TV moments. From Heavy D to Eartha Kitt, here are 15 guest stars who appeared on Living Single.
01
Eartha Kitt
Kitt played an eccentric client that Kyle (TC Carson) tries to impress and who he suspects has a bit of a crush on him. There was really no one else perfect for the role with Kitt adding the perfect amount of elegance and zaniness to the character.
r/r
02
Heavy D
In his recurring role as Darryl, Heavy D played Régine’s friend and brief love interest. Though things don’t work out between Daryl and Régine, they remained friends and, later, Régine stops him from marrying a golddigger, played by Vivica A. Fox.
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03
TLC
The girl group were a part of Overton’s guilty conscience, appearing in the handyman’s dreams every time he fell asleep during their videos.
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04
Isaiah Washington
Washington played one of Khadijah’s many love interests, a well-connected doctor who took the magazine editor along to one of his banquets, where things got a little tense after snobby guests insulted her.
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05
Monica
Singer Monica popped up in season three’s episode titled “Kiss of the Spider Man,” where she played the sister of Khadijah’s beau Teddy. Initially, Khadijah wanted to help Teddy’s sister get through a break up, but the afternoon turned into a nightmare as Teddy’s sis wore out her welcome.
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06
Kenya Moore
Long before she joined The Real Housewives of Atlanta, Moore appeared as Lisa DeLongpre on Living Single.
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07
Morris Chestnut
All the ladies wanted his attention when Hamilton Brown (Chestnut) moved into the building. However, Khadijah ended up being the not-so-lucky lady who landed a date with him, where Brown proved to be less than a gentleman.
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08
Terrence Howard
Maxine caught a lot of flack for dating a younger man, Brenda King (Howard), during season one’s “The Hand That Robs the Cradle.”
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09
Shemar Moore
Moore caused a few problems when he appeared on the show as Jon Marc, a classmate of Synclaire’s who kisses her during a study session.
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10
Bumper Robinson
Bumper Robinson played Ivan Ennis, an intern at Khadijah’s Flava Magazine. Ivan was so in love with Khadijah, but the magazine editor never showed any interest.
11
Kadeem Hardison
Hardison played Khadijah’s biggest rival, Marcus Hughes, who constantly scooped the magazine editor and attempted to steal her cover story.
12
Grant Hill
Hill played himself in an episode of the series, where Khadijah injured Hill during a game of basketball. He later asked her on a date, during which she received a piano serenade in the middle of a basketball court that left Régine jealous.
13
Brian McKnight
McKnight played himself during an episode, in which Kyle and Maxine attended his concert and breakup by the end of it.
14
Gladys Knight
Knight played Overton’s mom in an episode where Synclaire and her beau finally meet each other’s parents.
15
Khalil Kain
One of Régine’s many beaus, Kain played Keith. An artist and odd choice for the choosy Régine, in season three’s “Compromising Positions,” the pair got busted in a compromising position by Régine’s mom.
16
Dean Cain
Before voting for Trump, Cain appeared on Living Single as himself after Khadijah found his wallet and refused to give it to anyone else aside from Cain.

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