Dave Chappelle seems to have the funnier comedy show among the two. While Chris is also a great comedian, many people consider Dave Chappelle to have better shows for a number of reasons. Firstly, most people are easily able to relate to what Dave Chappelle jokes about.
Secondly, he has had roles in numerous high grade comedy movies. His roles in those movies kind of remind the audience of good of a comedian he is every time he is on the stage, so whatever he says sounds 10 times funnier automatically. That’s like a bonus he has. Otherwise, both are great comedians.