In 2000 Dave Chappelle's show Killin' Them Softly was recorded at Lincoln Theatre in Washington DC, being the comedians first major stand up comedy show. In the Dave Chappelle's show: Killin' Them Softly he talks about different topics from politics to social problems and personal relationships.
In 2002, Dave Chappelle played the "Conspiracy Brother" in the comedy movie Undercover Brother. Dave Chappelle's video Killin' Them Softly was released on DVD in July 2003. In 2003, Dave Chappelle stand up comedy show talent could be seen in the Richard Pryor tribute television documentary "Richard Pryor: I Ain't Dead Yet, #*%$@!!".
In 2003, Dave Chappelle made his own sketch comedy show: Chappelle's Show. Dave Chappelle's TV show touched many topics like pop culture, racial behaviour, and politics. Also, in Chappelle's Show, Dave Chappelle featured musical performers and the comedian portrayed different personalities. Chappelle's show was a big success, but also controversial mostly because of the social and political commentary that the comedian made. Chappelle's show was very popular and even Richard Pryor was a fan, stating that he had "passed the torch to Chappelle". It is a well-known fact that Dave Chappelle's comedy career was influenced by Richard Pryor.
Chappelle's show was so popular that in the first day of the release of the DVD with the second season of Chappelle's show, there were sold 500,000 copies. Chappelle's show on DVD was sold in 1,2 million copies in the first week. It became the best-selling DVD of a television show, being sold in over 3 million copies.
In 2004, Dave Chappelle was nominated twice with for a Emmy: Outstanding Variety, Music or Comedy Series and Outstanding Writing for a Variety, Music or Comedy Program - Nominee.
Dave Chappelle - Chappelle's Show. In June 2004, it was announced that Paramount Pictures wanted to do a Rick James movie, based on the popularity of Dave Chappelle Rick James sketch, but Dave Chappelle turned down the offer and the negotiations were stopped. In 2005 the comedian was nominated again for a Emmy: Outstanding Variety, Music or Comedy Special.
In 2004, Dave Chappelle For What It's Worth was taped. Dave Chappelle's stand up comedy show For What It's Worth was recorded in San Francisco at The Fillmore and the DVD came out one year later, in August 2005.
In 2004, during Dave Chappelle's stand up comedy show in Sacramento, California, the comedian shouted constantly "I'm Rick James, bitch" and then walked out of the stage. Dave Chappelle returned on the stage minutes later and stated that the popularity of Chappelle's show was standing between him and his stand up comedy career, which was the most important thing for him.
So, maybe for the fans that were present that day at his show in Sacramento, were not surprised by his decision, when in May 2005 Dave Chappelle disappeared in the middle of the third season of Chappelle's Show.
In 2005, Viacom offered Dave Chappelle a $55 million contract to produce Chappelle's Show for two more years, but having the freedom to do side projects. So, in May 2005, when Dave Chappelle abruptly left the show during the filming of Season 3 from Cahppelle's show, there were rumours about him taking drugs or being mentally instabile.
Not only that he left the production: Chappelle's Show, but the comedian also left the USA and went to South Africa. In an interview the comedian gave to Time Magazine in South Africa, denied any mental problems and drug problems and he said that the reasons he came to South Africa were to reflect on his career and his life. On the 18th of December 2005, Dave Chappelle was interviewed for Inside the Actors Studio and the show had its premier on the 12 of February 2006.
In 2006, the comedian Dave Chappelle explained his decisions, stating that he had left Chappelle's Show because the sketches were not his favourite form of comedy and that he was unhappy with the direction of the show. Also, Dave Chappelle stated that Chappelle's Show contained sketches that the comedian felt that were "socially irresponsible".
Dave Chappelle returned to stand up comedy and produced the successful Dave Chappelle's Block Party. On March 3, 2006, Dave Chappelle's Block Party was released by Rogue Pictures, a division of Universal Pictures. In February and March 2006, Dave Chappelle toured several cities to promote Dave Chappelle's Block Party.