Top Five Week: Favorite Chappelle’s Show Skits

Top Five week continues as I take a look back at the short-lived but much-loved Chappelle’s Show. I considered putting at least one Chappelle’s Show episode on yesterday’s list, but it was tough to narrow it down to one definitive episode.

Every week throughout its glorious two season run (I know, there was kind of a third season, but it doesn’t really count), the show would seemingly deliver at least one classic skit. But which were the best? Here’s my opinion: (Be warned, most of these videos contain at least some NSFW material)

5. Mad Real World

Maybe I just like the skit because it features a character named Tron. To this day, if somebody asks me what kind of drink I’d like, I often ask for a banana cognac. (And to this day, I’ve never actually received one.)–the-mad-real-world–pt–1—uncensored

4. Frontline – Clayton Bigsby

Featured on the first episode, I remember watching this and getting the same feeling I did when watching The Ben Stiller Show ten years earlier. I knew that if they could keep this up, it would be awesome.–frontline—-clayton-bigsby-pt–1—uncensored

3. Wayne Brady – Training Day

Maybe I’m just a bit twisted, but watching Wayne Brady snap a police officer’s neck is one of the funniest things I’ve ever seen.—uncensored

2. True Hollywood Stories – Prince

The Rick James THS skit got all the hype, and admittedly, it is awesome. But I think it may have gotten a bit played out. You can only hear people say, “I’m Rick James, bitch” so many times before you get tired of it.

I always found the Prince edition to be better. From fruity picks to “game, blouses,” there’s just so much greatness to be found here:—prince—uncensored


1. Kneehigh Park

Back in the good old days before Squinty moved to Las Vegas, we would often watch this skit during halftime of football games. And despite knowing what was coming, I’d still crack up every time.

Avenue Q got all the hype for their Sesame Street parody, but really, this came first and probably did it better. After all, Avenue Q didn’t feature Snoop Dogg.–1—uncensored


About The Cutter

I am the Cutter. I write some stuff. You might like it, you might not. Please decide for yourself.
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