Nine appearances from 1994 to 2014 and each time he was about fifteen pounds heaver. Other than that it was the same exact Chappelle we've all known to come and love. Click through if you want, but my favorite appearance is at the 44:03. It was right after Chappelle's Show wrapped it's first season in 2004 and you could tell how happy he was. Both of them were so energetic back in the day. Chappelle's still got it, but it's measured. Letterman just doesn't give a shit. Although I guess I wouldn't either if I was him. Simpler times. Have a great Tuesday, friends.