Every classic ’90s sitcom had that one episode where a superstar walked through the door and the whole living room lost it. We’re putting seven of the most iconic celebrity guest appearances side by side, and we need you to decide which show did it best.
Moesha: Kobe Bryant
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Before he became the Black Mamba, an 18 year old Kobe Bryant fresh out of the NBA Draft stepped onto the set of Moesha as Terry Hightower, Crenshaw High’s star basketball player. In the episode, which aired September 24, 1996, Terry asks Moesha for help on the SAT so he can hold onto his athletic future. The chemistry made sense, too. Months before the episode aired, Kobe had asked Brandy to his real life prom. The episode even closes with Moesha rocking a Lakers jersey with the number 8, the number Kobe wore when he started his career in Los Angeles. Kobe and his daughter Gianna died in a helicopter crash in January 2020, which makes this appearance hit even harder today.
Martin: The Notorious B.I.G.
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In Season 4, Episode 3, “Blow, Baby, Blow,” Biggie came to Detroit looking for background singers, and suddenly everybody Martin knew wanted their big break. Biggie played himself and didn’t miss a beat next to Martin Lawrence. Martin later told XXL that Biggie “had a real sense of humor” and barely had to try on camera. More than two decades after his death, it remains one of the most rewatched cameos in sitcom history.
The Steve Harvey Show: Lil’ Bow Wow
The Steve Harvey Show celebrated its 100th episode in February 2001 with Lil’ Bow Wow as himself. In “No Free Samples,” the young rapper wants to sample the Hi-Tops’ signature song, “Break Me Off a Piece of That Funk,” and gets in touch through Lovita, his old babysitter. Jermaine Dupri and Ron Isley joined in, turning the milestone episode into a full blown music moment.
Living Single: TLC
T-Boz, Left Eye, and Chilli brought their CrazySexyCool energy to the Flavor crew in Brooklyn, putting one of the biggest girl groups in the world in the same room as Khadijah, Synclaire, Max, and Regine. For a show built on Black women supporting each other, having all three members of TLC stop by felt like a perfect match. The appearance is also a reminder of the late Lisa “Left Eye” Lopes, who died in 2002.
The Jamie Foxx Show: Mary J. Blige
In “Papa Don’t Preach,” Mary J. Blige played Ola Mae, an aspiring R&B singer clashing with her father, played by Ron Isley, over her dreams of making it in music. Jamie helped Ola Mae find the courage to go for it, and the episode paid off with Mary performing her real single “I Can Love You.” Ron Isley showing up on both this show and The Steve Harvey Show only adds to his sitcom legacy.
Family Matters: Missy Elliott
Missy Elliott made a cameo in “Original Gangsta Dawg,” which aired December 5, 1997. The episode introduced Urkel’s hip hop cousin O.G.D., another Jaleel White character, who makes a terrible first impression on the Winslows by hitting on Laura and leading 3J astray. Missy’s appearance put one of hip hop’s most innovative artists right in the middle of CBS’s Friday night lineup.
The Fresh Prince of Bel-Air: Boyz II Men
Boyz II Men came through for a holiday episode while in Los Angeles for a radio special. Will sneaks into their recording session and almost gets tossed out before claiming he knows them from Philly. The twist is that Will once stole a girlfriend from one of the members. By the end, the group sings at baby Nicky’s christening, giving fans a hometown connection and a harmony moment in one episode.
Seven shows, seven legendary guests. Kobe, Biggie, Bow Wow, TLC, Mary J. Blige, Missy Elliott, and Boyz II Men all helped define what made the ’90s sitcom era special. Now it’s your turn: which show had the best celebrity guest appearance?
