Top 10 Times In Living Color Roasted Celebs

#10: Butt-Out Jeans

Prince
Comedian Dave Chappelle may possess the most iconic portrayal of Prince in his back pocket, but Jamie Foxx didn’t even have pockets when he imitated the Purple One back on “In Living Color.” This fake commercial for “Butt-Out Jeans” starts out a little avant-garde, with some close-up camera work moving back-and-forth between a conversation between Prince and two other men. The pair keep telling Prince to “butt out” of their conversation, as Foxx’s impression of Prince rides hard upon the singer’s infamous libidinousness and reported dalliances with his musical collaborators. Finally, Prince reveals his naked butt-cheeks to the world in a pair of denim chaps, and dances behind the announcer’s voice-over.

#9: Love Connection

Mike Tyson
“In Living Color” wasted no time in taking even the most high-profile celebrities to task. Heck, the show’s pilot episode featured an infamous take on the TV show “Love Connection,” featuring Keenen Ivory Wayans as Mike Tyson and Kim Coles as his former spouse, Robin Givens. The show continued to use Tyson as a proverbial punching bag, as well, airing a running “Three Men and a Baby” spoof starring Tyson, Sugar Ray Leonard and Muhammad Ali. Oh, but wait: there’s more! “Late Night with Mike Tyson” got two birds with one stone, riffing on both Tyson’s aggressive reputation, as well as the talk show format of another roast subject on this list, Arsenio Hall.

#8: When a Man Needs a Big Hit

Michael Bolton
“In Living Color” loved to say out loud what many in the entertainment industry were thinking inside of their collective heads. The show, as a result, struck gold with sketches like this one, which took to task singers like Michael Bolton adapting old soul songs for chart success. The lyrics to “When a Man Needs a Big Hit” say as much when Jim Carrey sings about “swiping another song from a long-dead brother.” Additionally, Carrey’s mannerisms as Bolton emphasize the singer’s penchant for vocal histrionics and over-the-top, emotive theatrics. So over-the-top, in fact, that Carrey blows up during the finale!

#7: Am I Black or White?

Michael Jackson
Tommy Davidson and the “In Living Color” writers deliver a LOT of commentary within the scant, three minute running time of “Am I Black or White?” The sketch satirizes the music video itself, from the body-morphing technology, to the controversial coda where Michael angrily trashes a car. Elsewhere, the lyrics are a historical run-down of Jackson’s career highs and lows. The money, the fame, the plastic surgery, and the accusations: it’s all here on display. “Am I Black or White” saves the most stinging joke for the end, however, when Michael is arrested by a police officer:

#6: Do It Yourself Kit

Milli Vanilli
Milli Vanilli was barely a year into their U.S. commercial success back in 1990, but the bloom was already starting to fall off the rose. Accusations of lip syncing were growing louder around the time “In Living Color” decided to roast the group back in April of that year. The skit “Milli Vanilli’s Do it Yourself Kit” showcased the group as a pair of dimwitted wannabees who seemed to know that their time in the spotlight was just about up. Keenen and Damon Wayans lean into the duo’s dance moves, their accents and hairstyles, basically insinuating that just about any “two jerks” could be Milli Vanilli.

#5: The Butt of Jokes

Arsenio Hall
Keenen Ivory Wayans was fitted for a couple of…let’s say “exaggerated” prosthetics whenever he roasted Arsenio Hall. An absurdly long index finger was one, while the other was…well, it was a BIG ‘ol butt. Hall was a frequent target on “In Living Color,” from his talk show format to his relationship with Eddie Murphy. “In Living Color” even did a parody of “Cape Fear” titled, you guessed it, “Cape Rear,” where Arsenio seeks vengeance for Murphy allegedly hanging him out to dry. Are all of these pair points against Arsenio? We’re not sure, but Keenen Ivory Wayans certainly seems to be having a good time whenever these skits show up!

#4: Spike’s Joint

Spike Lee
An oral history of “In Living Color” that was published in the Hollywood Reporter back in 2019 quotes Tommy Davidson’s recollection of how celebs like Spike Lee and Arsenio Hall weren’t exactly fond of their respective spoofs. It’s sort of easy to see why, too, since “Spike’s Joint” is an incredibly sharp and effective dig about Spike Lee’s reported demeanor and legacy as a filmmaker. His fictional store here sells everything from knock-off Air Jordans, “riot sized” trash cans and free copies of “School Daze.” Meanwhile, the escalating tension within the joint directly reflects Lee’s classic film, “Do the Right Thing.” Heck, the skit even features Rosie Perez!

#3: Lil Richard’s Playhouse

Little Richard
Many of the best roasts and parodies are done with love, admiring the best qualities about a performer, while also acknowledging all of the potential eccentricities that often follow some of our favorite celebs. “Lil Richard’s Playhouse” features Keenen Ivory Wayans doing a pretty damn good Little Richard impression, aided by a fabulously shiny blue outfit. The voice is on point, the hair is on point, and Wayans’ repeated outbursts of “shut up!” just make us laugh every single time. The skit also brings up just how influential Richard has been over the years, as he alleges artistic theft from just about everyone you could mention. Oh, and he never did finish telling us that story.…

#2: Oprah Wants Some Snacks

Oprah Winfrey
Oprah Winfrey may be considered to be something of a sacred cow with regards to parody these days, but nothing was stopping the writer’s room over at “In Living Color” from having their cake and eating it, too. Their parody of “The Oprah Winfrey Show” is twofold. For starters, it riffs upon the often-trashy landscape of talk show TV that flourished during the 1980s and ‘90s. High concept topics are eschewed for trashy relationship talk, but all Oprah really wants are some snacks. The other side of the sketch is playing up Winfrey’s real-life relationship with her weight. This is played for laughs, as the host is displayed engaging in increasingly comedic bouts of fast-paced munching and crunching.

#1: White, White Baby

Vanilla Ice
It’s probably the most well-known and remembered musical parody ever performed on “In Living Color.” Granted, the rise of Vanilla Ice in the nineties was ripe for parody, but no one hit the nail on the proverbial head better than this sketch, “White, White Baby.” Jim Carrey embodies all of Ice’s vocal mannerisms and dance moves, while also commenting upon the overall “lameness” that was the original “Ice Ice Baby” and its rise to fame. This wasn’t the only time Carrey would take a white rapper to task, either, as reggae-pop singer Snow was also skewered by Carrey and “In Living Color” with the skit, “Imposter.”