30 Years of Laughs: Living Single’s Most Memorable Guest Stars

If you need a powerful femme fatale who brings men to their knees, you call Eartha Kitt. In the Season 3 episode “He Works Hard for the Money,” Kyle finds himself caught up in the wild life of actress Jacqueline Richards. Their duet is one of the show’s most memorable moments.

A very young Terrence Howard plays a college freshman who Max briefly dates, causing a lot of ridiculous nicknames and one-liners.

The A Different World star was one of the many charming men who underestimated Khadijah. He thought he smile and few flirtatious lines would get him the scoop. It’s like a TV passing of the torch.

You can check Living Single off Nia Long’s bingo card of Black entertainment essentials. In Season 1, she guest starred as a Flava photographer who Kyle fell for, but who was still hurting from a recent break up. You can definitely see hints of the star she would become.

Shemar Moore made the guest star rounds as the sex symbol who popped up just to get women worked up and possibly take off his shirt.

The rap legend played Regine’s boyfriend Darryl in three episodes. He was obviously too mature and well-rounded for her, so we always wondered how he fell for her gold digging ways.

The least surprising name on this list is Jenifer Lewis. Honestly, it would have been more shocking if the unquestioned Queen of Black Entertainment hadn’t appeared on Living Single at some point.

Mario Van Peebles was hilarious as overly dramatic weatherman Cole Front, while his legendary father Melvin Van Peebles has that old school charm down as Warner Devant. Regine ended up dating both and I really can’t be mad at her about it.

T-Boz actually appeared on the show twice. She guest-starred with TLC when Overton couldn’t stop dreaming about them, then later in the series’ run she returned as a hitchhiker who got the guys in trouble.

Before she was one of The Real Housewives, Kenya Moore had a blink and you miss it moment as Kyle’s date Lisa DeLongPre.

Gladys Knight played Overton’s mom, and she fit in perfectly with the sweet-natured character John Henton established.

Here’s the thing: CCH Pounder never disappoints. As Max’s mom, she gives a brilliant glimpse at where the Maverick got her badass persona from.

Giancarlo Esposito is famous for playing unforgettable villains. In this Season 3 episode, we see that magnetism when he plays one of Max’s clients, who may be guilty, but she’s still drawn in. We’ve all been there with Giancarlo Esposito.

Morris Chestnut usually plays a smooth-talking charmer who women are instantly attracted to. In this appearance, he plays against type, when it turns out he’s actually a nightmare.