Dave Chappelle

Dave Chappelle's return after a 12-year hiatus with 2017's *The Age of Spin* and *Deep in the Heart of Texas* earned him 3 consecutive Grammy Awards for Best Comedy Album (2018–2020), a feat faster than any other stand-up on this list. His *Chappelle's Show* (2003–2006) became Comedy Central's highest-rated show ever and the best-selling TV DVD of 2004, with 3.2 million units sold. Chappelle received the Mark Twain Prize in 2019, making him 2 years younger than the average recipient. His material holds a 95% audience approval rating across specials, outperforming the typical performer by 20%.