Dave Chappelle

Dave Chappelle is one of the defining comedians of the 21st century. The thoughtful, defiant, and boundary-pushing stand up and sketch star experienced his breakthrough in the mid-2000s with Chappelle's Show after ten years spent working the stand-up circuit and appearing on television and film whenever he could. Despite -- or perhaps because of -- the show's runaway success, he quit in the middle of its third season, then retreated from the spotlight. Over the next decade, he occasionally appeared at comedy clubs, finally returning to the stage in the late 2010s with regular touring and comedy specials. After striking a deal with Netflix for a series of comedy specials, the comic began releasing them as albums, and Chappelle won Grammy awards for releases like The Age of Spin & Deep in the Heart of Texas (2017), The Closer (2023), and The Dreamer (2024).