By coincidence, I went through every episode of The Chappelle Show in the past couple of days. There are some very unfunny sketches in the first couple of episodes, but by the end of Season 1 and for pretty much all of Season 2, the show was firing on all cylinders. I miss showing up to middle school (maybe freshman year of HS, I forget) and hearing random shouts of "I'm Rick James, bitch!" coming from out of nowhere. Pretty much everyone in my suburban school watched the show religiously.
It's a shame that he couldn't keep it together for Season 3 (unless there's some alternate theory of what happened that doesn't boil down to "Dave lost his gat'damn mind" that I'm not aware of). I think it could have been great for at least another season, if not more.
The episodes with Charlie Murphy and the "I'm rich, Biotch!" guy hosting were just....ugg. Some of those sketches though, like Gary Coleman as a security guard....good lord... I nearly tore out my stitches laughing the other day. He obviously had so many more ideas. Oh well.