Christian Finnegan's Top 5 Chappelle's Show Sketches | Chappelle's Show | Comedy Central

Christian Finnegan is a stand-up comedian, writer and actor based in New York City. He currently can be seen as a panelist on VH1's hit series Best Week Ever. His debut comedy album, Two for Flinching, is available on Comedy Central records. Finnegan will be taping his first one hour stand-up special October 25th at the Trocadero Theater in Philadelphia. For tickets and more info, go to his website.

#5 - He's Rick James!


I hesitate to include this sketch, just because it seems so obvious. But really, how can you leave it out of the top five? When the dust settles and people talk about what was going on, comedy-wise, in the early 21st Century, they'll talk about South Park, they'll talk about Borat, and they'll talk about Chappelle's Show. And when they do, the Rick James sketch is probably the first thing they'll mention. (Full disclosure: I also resisted listing The Mad Real World, just because it felt douche-y and self-serving. But yeah, That one was pretty damn funny too.)

#4 - Wayne Brady


Maybe the best 'playing against type' comedy performance of all time. Its easy to poke fun at Wayne Brady because... well, because your mom thinks he's so hilarious. But in my book, Mr. Brady has a free pass for the rest of his career. He can spend the net thirty years improvising offensively inoffensive ditties for middle-aged dorks and I'll still say, "Yeah, but did you see him in that Chappelle's Show sketch? That dude is hilarious."

#3 - Racial Draft


What makes Chappelle's take on race so remarkable is that it's simultaneously nuanced and fearless. Most racial humor is lazy-it's the same hack stereotypes you've heard a thousand times before. Either that, or it's so 'safe' that it resembles nothing people actually experience in the real world. But Dave attacks stuff with such confident specificity, it looks effortless. He's kind of a comedy Obama-you watch him and you say to yourself, "Yeah, he pretty much nailed it."

#2 - Basketball with Prince


I feel bad for kids nowadays because they didn't get to grow up when Prince was still a big deal. No musical artist since has matched his fascinating combination of genius and ridiculousness. A lot of great artists pretend to be weirdoes and even more weirdos convince themselves they're great artists. Prince was (and still is) the real deal and Dave captured that creepy pansexual Prince vibe perfectly. The scene where Prince dunks the ball and then hangs seductively on the rim is one of my favorite moments of the show.

#1 - Clayton Bigsby


After I got cast in the 'Mad Real World', I went in to the Comedy Central offices to do what they call a "table read", which is pretty much exactly what it sounds like. On that same day, they were reading the Clayton Bigsby sketch. I remember thinking, "Wow, this is hilarious. But I wonder how funny it will be once the censors carve it up." Much to my surprise, the sketch aired exactly how I remembered it. Huge, huge balls.