Dave Chappelle has been nominated six times for Best Comedy Album at the Grammys and now has won six times, continuing his undefeated streak in the category with his Feb. 2 victory for The Dreamer.

Dave Chappelle has taken home the Grammy for best comedy album, marking his fifth win in the category. The comedian won for ...

Dave Chappelle won best comedy album at the 2025 Grammys on Sunday, his third win in a row in the category and sixth win overall. The Recording Academy presented the comedy album trophy during the ...

Yellow Springs-based comedian Dave Chappelle won his sixth Grammy and third in a row for best comedy album Sunday at the 67th annual Grammy Awards. Chappelle won for “The Dreamer,” which ...

Chappelle received three consecutive Grammy Awards for best comedy album with 2017's The Age of Spin & Deep in the Heart of Texas, 2019's Equanimity & the Bird Revelation and 2020's Sticks & Stones.