Dave Chappelle: Killin' Them Softly (2000)

Dave Chappelle: Killin' Them Softly (2000) is the tightest hour of observational comedy about race ever filmed, earning a perfect 100% Rotten Tomatoes score from critics. Shot in Washington D.C.’s Lincoln Theatre, with the "Black Bush" routine alone generating 3.2 million YouTube views before the 2020 election. While Richard Pryor revolutionized vulnerability, Chappelle perfected precision, weaving sociopolitical critique into an endlessly quotable hour.