Coolio’s influence on ’90s and 2000s pop culture is legendary. Following news of his death on Sept. 28, fans on Twitter were quick to reminisce about the rapper’s musical and acting legacy. “The way tv and hip-hop were so connected in the 90s is something i’ll never forget,” one Twitter user captioned a video of Coolio performing the “Kenan & Kel” theme song alongside Kenan Thompson and Kel Mitchell. “and it gave us one of the best songs in the kenan and kel theme by coolio. rest in peace.”
In addition to giving us iconic hits like “Gangsta’s Paradise,” Coolio left his mark on screen. Over the course of his career, the multihyphenate starred in dozens of movies – both as characters and as himself – and made unforgettable TV guest appearances that still make us smile every time we catch a rerun.
While his music was the talent that made him a household name, Coolio’s acting abilities never failed to impress. In 1995, he appeared on “Martin” alongside Outkast, Dolemite, Pam Grier, and other celebrities taking part in a ’70s contest hosted by Martin Lawrence. A year later, in 1996, the singer emerged like magic from a poster in an alleyway to give advice to none other than Sabrina Spellman (Melissa Joan Hart) on “Sabrina the Teenage Witch.” But perhaps one of Coolio’s most memorable TV moments came in 1998, when he joined Fran Drescher on “The Nanny” as a geeky gift wrapper named Irwin whose musical rapping skills were surprisingly incredible.
Ahead, relive a few of Coolio’s best TV guest appearances – yes, including the “Kenan & Kel” theme song.
Related: 375 Things You’ll Remember If You Grew Up in the ’90s
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"Martin" (1995)
In 1995, Coolio made his onscreen debut as a gangster on “The Parent ‘Hood” in the episode “Trust a Move.” The same year, the rapper made a guest appearance as himself on “Martin” alongside celebrities like Pam Grier, Outkast, Ja’Net Dubois, Dolemite, Antonio Fargas, and more. During the episode, “All the Players Came,” Coolio joins his fellow celebrity guest stars in participating in a ’70s-themed contest hosted by Lawrence.
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"Dangerous Minds" (1996)
In addition to sharing his song “Gangsta’s Paradise” on the “Dangerous Minds” film soundtrack, Coolio appeared in the TV-show adaptation’s pilot episode as a sex educator.
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"Sabrina the Teenage Witch" (1996)
While “Sabrina the Teenage Witch” was packed with celebrity guest appearances over its seven-year run, one of the show’s most memorable guests was Coolio. During the episode “A Girl and Her Cat,” in which Sabrina searches for Salem after he goes missing, Coolio appears in an alleyway, emerging from a poster of himself to give her advice.
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"Early Edition" (1999)
“Early Edition” was a fantasy comedy-drama about a man who receives a copy of the newspaper one day before it’s published and uses the information to prevent terrible events from occurring. In the episode “Number One with a Bullet,” Coolio appears as Julius ‘C-Roc’ Ruby, a famous rapper whose career has begun to stall. In an attempt to get back to his roots, C-Roc makes a tour stop in his hometown, where he meets the show’s main cast, who help him re-evaluate his life.
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"Malcolm & Eddie" (1999)
“Malcolm & Eddie” starred Malcolm-Jamal Warner and Eddie Griffin as opposing roommates who often land themselves in hilarious and unexpected scenarios. In the episode “Daddio,” Coolio plays Troy Jensen, a contractor who has bid on the construction of a new Fifty-Fifty Club in Chicago that Malcolm and Eddie are interested in. When Troy’s wife, a nurse, is unexpectedly called into the hospital, he’s left to take care of their three children – 7-year-old Rome, 10-year-old Cairo, and 12-year-old Geneva. During the episode, Malcolm and Eddie do their best to help Troy look after his children while also trying to negotiate a business deal with him.
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"Arli$$" (2000)
“Arli$$” was a dark comedy series about a high-level professional sports executive with a penchant for saying “yes” to everything his clients and employees ask of him. In the episode “It’s Who You Know,” Coolio plays Ernest. During the episode, the lead character, Arliss (Robert Wuhl), makes a special offer to the NBA’s unofficial weed dealer in the hopes of convincing him to retire.
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"Charmed" (2002)
Joining good witches Prue Halliwell (Shannen Doherty), Piper Halliwell (Holly Marie Combs), and Phoebe Halliwell (Alyssa Milano), Coolio made a special guest appearance on “Charmed” in 2002 as a Lazarus demon. These are hot-headed, high-level demons with telekinetic abilities and the power to reconstruct themselves after their bodies have been destroyed. The longer they’re released, the more powerful they grow, which doesn’t bode well for the sisters in this supernatural wedding episode.
