Why Dave Chappelle Abandoned a $50 Million Deal at the Height of His Popularity

Finding out why Dave Chappelle walked away from his hit show at the peak of its popularity.

Dave Chappelle at the Laugh Factory, New York City in 2004. Image property of Stuart Ramson and Shutterstock.

Dave Chappelle is fundamental stand-up comedian and actor standing toe to toe with legends like Richard Pryor, Bernie Mac and Eddie Murphy.

Chappelle’s success reached meteoric heights in 2003 when he partnered with Comedy Central and writer Brennan to create his hit sketch comedy series ‘Chappelle’s Show’.

The show's format was pre-recorded skits and live music performances from artists like Erykah Badu and DMX. Chappelle played various characters like Tyrone Biggums a crackhead and celebrities like Prince, Rick James or Samuel L. Jackson. The show's cast also featured Charlie Murphy, Donnell Rawlings and Paul Mooney.

The show became the best-selling TV show on DVD with over 1.2 million sold within its first week alone.

The genius of the show was in its excellent writing satirising many elements of black and pop culture at the time and spawned many early internet memes.

After the virality of his ‘Rick James’ skit, Chappelle became very jaded with the show, notably with Dave performing live stand-up in 2004 in which the crowd became obnoxious chanting the “I’m Rick James, bitch” catchphrase to Chappelle’s dismay saying the show was ruining his life.

Chappelle in the infamous Rick James skit. Image property of Comedy Central.

The third season was meant to debut in mid-2005 but was delayed when Chappelle walked off set abruptly and flew to South Africa to avoid tabloid harassment and politics of Hollywood.

Chappelle said he was disappointed with the direction the show had taken and was under tremendous stress. Chappelle walked away from the show leaving a $50 million deal behind.

In a 2006 interview with Orpah Winfrey, Chappelle said celebrities reaching the next echelon of their career often take large sums of money and end up going crazy.

“I go home and make the kids some integrity sandwiches.”

It was said that Chappelle was open to returning to the show if his demands were met. Chappelle wanted half the DVD proceeds to be donated to charity — however, Comedy Central failed to reach his demands.

In July 2006, Comedy Central released the third and final season without Chappelle’s input. The show left the live segments to Charlie Murphy and Donnell Rawlings and dubbed them The Lost Episodes.

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