Remembering Prince & Dave Chappelle’s Iconic Sketch Of The Late Musician

Dave Chappelle, Chappelle Show, Comedy Central, 042216
Comedy Central

If you were alive in the early ’00s, then there is a 99% chance that you were obsessed with Dave Chappelle‘s Chappelle’s Show and most importantly, the segment called “Charlie Murphy’s True Hollywood Stories”. In what is now one of the most iconic comedic sketches of all time, Charlie describes the time he and his younger bother Eddie Murphy hung out with Prince at his home back in 1985.


In the sketch, Prince, who is played by Chappelle, decides he’s tired of lounging around and listening to music. Instead, he and his band The Revolution challenge Charlie, Eddie and their crew to a basketball game. If you know anything about the legendary entertainer, then you know that he was a very petite man, and he also dressed rather flamboyantly. Murphy called it a, “Zoro-type outfit like something a figure-skater would wear.” As a result, Charlie did not take Prince’s hooping skills seriously. That was Charlie’s first mistake. As Prince told Tavis Smiley back in 1998, “I can’t be played. A person trying to play me plays themselves.” In the game that has now gone down in history as “The Shirts Against the Blouses”, Prince and the Revolution humiliated Charlie’s team.


And yet, being the amazing host that he is, Prince still served his guests pancakes after their loss.

Watch the hilarious sketch below:

The best part about the entire thing is the fact that the late Purple Rain singer confirmed all of this did actually happen and that he adored Chappelle and Murphy for doing the sketch. He even released the song “Breakfast Can Wait” in 2014, which was inspired by the sketch using Dave Chappelle as the single’s cover art. Charlie Murphy learned a very real lesson the day be played basketball with Prince, and that’s to never judge a book by it’s cover.