We all know how fantastic Chappelle’s Show was during its all too short run on Comedy Central a decade ago. The show made Dave Chappelle a comedy superstar and provided a place for stand-ups like Bill Burr to sharpen their comedic acting chops. After Dave called it quits, the show’s featured sketch players returned to the comedy club circuit while taking acting parts here and there, occasionally crossing paths on different online and TV projects.
A few weeks ago I highlighted Charlie Murphy’s best sketches from the series, and we’ve thoroughly enjoyed tracking Dave’s late night talk show appearances and historical block of shows at Radio City Music Hall. Now it’s time to find out what the rest of the Chappelle’s Show gang has been up to over the last decade.
Neal Brennan
Friend of UPROXX, Neal Brennan — the man half responsible for creating Comedy Central’s biggest show ever — started his career writing jokes for Jenny McCarthy on MTV’s 90s dating show, Singled Out. (Well, he was likely writing jokes for Chris Hardwick.) Brennan received three Emmy nominations for his work on Chappelle’s Show, but after it ended we didn’t hear much from him. The fallout from Dave leaving took its toll on their friendship and in 2009 Brennan told The New York Times that their relationship was “charred” and he didn’t envision them working together again. In 2011, Brennan revealed on Joe Rogan’s podcast that his feelings on working with Chappelle had softened and they had become friendly again.
Brennan is a busy man these days, co-hosting his podcast “The Champs” with fellow comic Moshe Kasher and directing TV episodes for New Girl, Inside Amy Schumer, and The Mindy project. Brennan stopped performing stand-up during the the last season of Chappelle’s Show because, as he tells it, he didn’t want to get on stage and have people yell “Where’s Dave?” The writer/director has returned to stand-up comedy and performs regularly in Los Angeles where he taped a one hour special last year, Women and Black Dudes.
Donnell Rawlings
Donnell Rawlings (or Ashy Larry as you probably know him) was in more Chappelle’s Show sketches than any other cast member after Dave himself. After the show came to a screeching halt Rawlings took Ashy Larry to the web, appearing in a series of online sketch videos called From Ashy to Classy where he would visit classy establishments under the name Ashford Lawrence. As far as continued work in television, Donnell Rawlings has landed some pretty good parts over the years, most notably playing ex-con Day-Day Price in season five of The Wire. Recently he’s appeared as one of the talking heads on MTV’s Guy Code and Guy Court where he judges guys who have been accused of breaking the guy code. Rawlings is also clocking in some major miles on the stand-up circuit, hitting clubs at least two weeks a month through the rest of 2014.
Charlie Murphy
Next to Chappelle, Charlie Murphy was without a doubt the most popular featured player on the show, though he only appeared in 14 of the show’s 33 episodes. He hasn’t found a television platform as big as Chappelle’s Show since it ended in 2004, but the series did more for his career than two decades of hanging out with his brother ever did. In 2009, he teamed up with ex-Chappelle’s Show cast member Donnell Rawlings to try and recapture some of the show’s magic for Crackle.com in the online series Charlie Murphy’s Crash Comedy. Unfortunately, it lacked the one thing that made Chappelle’s Show a success – Dave Chappelle. It only lasted 13 episodes. Murphy’s made good use of his distinct voice though, providing the voice of Ed Wuncler III for five seasons on The Boondocks, a pimp character in GTA: San Adreas, and a dog in Eddie Murphy’s 2007 film, Norbit. In 2009, Murphy lost his wife, Tisha Taylor after 12 years of marriage and the year later dedicated his one hour Comedy Central special, Charlie Murphy, I Will Not Apologize to her. Currently, he’s a regular on the TBS sitcom Are We There Yet? and is filming a new TV series called Black Jesus.
Guillermo Díaz
Guillermo Díaz appeared numerous episodes throughout the series, including in one of the show’s debut sketches, “Popcopy.” Díaz is an in-demand character actor and had a lengthy acting resume before teaming up with Dave Chappelle for a second time after co-starring in Half Baked. Like any seasoned character actor, he’s appeared on Law & Order, and was a recurring character on Weeds, playing Mexican gangster Guillermo. The openly gay Cuban actor currently is filming the fifth season of Scandal.
Christian Finnegan
Stand-up Christian Finnegan only appeared in one episode of the show, but his “Mad Real World” sketch was so popular that it was only fitting to include him in this article. (If your character’s dad gets shivved and your girlfriend sleeps with the entire house you get an instant spot on the list.) Finnegan has slimmed down considerably from those days — he dropped 88 pounds in 2006 — and following his appearance on the show joined Tough Crowd With Colin Quinn as a staff writer. In 2010 he appeared as the ticket agent in the Tom Cruise action comedy Knight and Day before joining fellow Chappelle’s Show cast member Charlie Murphy on the TV cast of Are We There Yet?
Anthony Berry
Unfortunately there is little info out there on the show’s oldest cast member, Anthony Berry. Hiss only other IMDB credits are a 2013 episode of Maury and a documentary called Furious Beauty.
