There is virtually no moment in this film that isn't uncomfortably racist. While I understand Spike Lee's motives for making Bamboozled, it remains very difficult to enjoy the film as a movie on its own and not as a cultural and political statement. While the performances were great, the idea of a satirical minstrel show actually becoming popular in this country seems sickeningly possible.
That isn't to say Bamboozled didn't have its brilliant moments. The ending, for example, was ingenious and watching Damon Wayans's character slowly lose his grip with reality was really smart filmmaking. The problem with this film is it's hard to watch because it's almost impossible to enjoy.