Charlie Murphy, one of the funniest and most underrated comedians, died on Wednesday after a battle with leukaemia. Murphy, who was 57, never achieved the fame his brother Eddie has, but his work, particularly with Dave Chappelle, remains iconic. He also appeared in films including Jungle Fever, Night at the Museum, and Lottery Ticket. Two of his funniest and most successful skits on The Chappelle Show came from him Charlie Murphy’s True HollyWood Stories of Rick James (part 1, runtime 05:06 and part 2, runtime 03:24) and Prince (runtime 05:05). You can catch other famous Murphy sketches from the Chappelle show including him as Tyree in The Mad Real World, The Playa Haters’ Ball, and his voice as Stinky from Kneehigh Park. Chappelle Show aside, The Wrap reminds that Murphy left a richer legacy including appearances in Spike Lee’s Mo’ Better Blues, The Boondocks, Jungle Fever, and also providing voice over for the Grand Theft Auto: San Andreas videogame.