Ranking the best sketches in Dave Chappelle’s seminal Chappelle’s Show is no easy feat. The show has transcended pop culture—becoming a lightning rod for topics that no one would speak about, and for social issues that are still a problem to this day. It’s inconceivable that the show would have even flourished this much in a Bush Presidency, with its dense writing about race, identity, and politics—but a truthful brand of comedy was the cure all that we needed in the post-9/11 world.
Digging through hours of the show wasn’t something that I didn’t look forward to, but I did figure that I’d give a disclaimer to why things are ranked how they are. Sure, the punchlines and memes were funny, but Chappelle’s Show was much more than that—it made you think. This ranking takes the most important cultural moments, over the ones you repeated at your class/watercooler/Myspace account back in 2003. Sketches that stood the test of time, and probably wouldn’t make Chappelle himself cringe if you recited them in public (Looking at you, people who still shout “I’m Rick James, bitch!” at him). So here it is, the ranking of the most important Chappelle’s Show sketches.