4. Dave Chappelle's Block Party

I caught this on cable the other night, and I couldn't have been happier. I thought it was great the first (and only) time I'd seen it, which was a few years ago, and it got me again. Great story, funny jokes, well made... oh, and the music, of course.

At the height of his fame, Dave Chappelle decided to throw a block party for a Brooklyn neighborhood - free of charge, anybody welcome, and by total surprise (well, until 2 days before). The crowd that swarmed the block had no idea who would be performing, and they were treated to a line-up of some of the best and most respected hip-hop artists and musicians in the industry. Truly this was an insane show, Chappelle declaring it "the concert I've always wanted to see." From Kanye West to Mos Def to The Roots and much more, the night was capped by the sudden, one-night reunion of The Fugees.
It's no surprise Chappelle asked these particular artists - they're some of the most socially conscious and revered people in the game. Who else would agree to be a part of such an event, a free show (funded completely by Chappelle) dedicated to the spirit of community?

Woven into the concert footage is the documentary, consisting mostly of Chappelle's trip to rural Ohio to recruit some party-goers, including middle-aged white folks and a small collegiate marching band, as well as back-stage clips and discussions with the musicians and Chappelle. The interactions and conversation are fascinating, Chappelle shows his off-screen persona yet is still hilarious, and the emotional payoff is moving. A great show, a great film, and all for the greater good. And according to Chappelle, the greatest night of his career.