Niggar Family (3) vs. Playa Hater's Ball (2)
It has taken months to finish this project, less because of the amount of content to digest, and more because of fear. I've reached different points, at different occasions, where I couldn't make a decision, prompting me to put it on the shelf for a series of weeks. This matchup was one of those points.
"Playa Hater's Ball" is, without exception, the most quotable sketch in Chappelle's Show history. For the duration of the sketch, it doesn't calm down one bit, just hitting you with line after line. I'll never get over the fact that, during the photo flip, Dave said that Diddy looked "like Malcolm X before he converted to Islam." And the decision to use the take when they all explode in laughter after the Rosie O'Donnell line "she wears underwear with dick-holes in them" was just genius. "Niggar Family" has fewer memorable lines, but what it lacks in quips it makes up for by being one of the smartest comedy sketches. Ever. He gave a white family the last name "Niggar." When the mom officially breaks the seal by commenting on a family picture, saying, "She's got those Niggar lips," it's cripplingly uncomfortable and hilarious. Watching and hearing white people say "Niggar" over and over again, in the masterful context that Chappelle set up, is still jarring, even when you've seen the sketch hundreds of times and know when it's coming. And then there's Chappelle's milkman character. Between "I know not to get between a Niggar and their pork — might get my fingers bit," "I know how forgetful you Niggars are about paying your bills," and "All right, peace, Niggar," there's just no way this doesn't make it to the next round. It seems weird to knock out "Playa Hater's Ball," given that I've quoted it twice today, but this is the end of the road.