This is the movie that got me turned on to Mr Lee. When I rented this movie just a few years ago I watched it 3 times and then watched it with the audio commentary. I found the movie *that* interesting. Also, the movie has a few layers to its plot so each time one watches it, they're sure to pick up on something new.
The characters are also great - I especially love Damon Wayan's boss who is a caucasian married to a black woman and tells Damon "I'm more black than you are" From that point on, you know this movie is going to put a lot of stuff in your face.
The basic premise - Damon's character is tired of the types of shows with black people that show on tv nowadays. It's all very stereotypical (think this summer's "Method and Red" on fox) and he wants to do something creative. His boss wants something along the lines of "homeboys in outer space". Damon's character is so incensed that he decides he'll get fired in order to break his contract.
What could be better for getting him fired than to make the most racist and ignorant show on tv? He decides to make a show called "Bamboozled" which will recreate the blackface shows of the 30s and 40s only it will be black actors putting on blackface. There's only one problem with his plan: the show becomes a hit.
The rest of the movie shows what happens to the rest of the characters in the style of a Shakesperean tragedy. In other words, a few things don't quite go according to plan and everyone suffers. (ie Romeo & Juliet, MacBeth, etc)
Another thing that makes this movie so awesome is the fictitious commercial spot during the show Bamboozled. Spike Lee takes a pot shot at Tommy Hilfigger's alleged marketing directed at blacks with another brand whose name I can't write or my review will be banned. You'll be shocked, but in a revealing sort of way.