In 2003, Chappelle became more widely known for his sketch comedy television series, Chappelle's Show, also co-written with Brennan, which ran until his retirement from the show two years later. After leaving the show, Chappelle returned to performing stand-up comedy across the U.S. By 2006, Chappelle was called the "comic genius of America" by Esquire and, in 2013, "the best" by a Billboard writer. In 2017, Rolling Stone ranked him No. 9 in their "50 Best Stand Up Comics of All Time."
In 2016, he signed a $20 million-per-release comedy-special deal with Netflix and in 2017, he produced and they released four of his specials in one year.
Chappelle received his first Emmy Award in 2017 for his guest appearance on Saturday Night Live. In 2018, he received a Grammy Award for his Netflix specials The Age of Spin & Deep in the Heart of Texas. "Equanimity," his Netflix special, was nominated in 2018 for three Emmys and received the award for Outstanding Variety Special (Pre-Recorded).