I originally saw this several years ago while I was sitting on the couch and got stuck watching it on HBO. With the remote out of my reach I decided to go with it and was awaiting a miserable movie that I had been avoiding for a year. So it started off and I wasn't very optimistic about it, but after about ten minutes I found myself laughing. The complete opposite as I was expecting. The comedy was smart, the acting pretty good considering, the cast worked very well together, and the story (though slightly awkward and fake) was actually quite entertaining.
Three convict brothers manage to escape their sentence and eventually go in search of their fortune. The movie is set in the 1930's. So along the way, they encounter a number of funny and interesting charatcers. All have a different story or achievement they are striving for. Really the majority of the movie may seem random. Some may say it was pointless and boring, but if you look for the smart comedy (and occasionally stupid) that is integrated into the movie, I'm sure you'll enjoy this one.
I liked the performances given by George Clooney, John Turturro, and Tim Blake Nelson. All of them did very well in their roles, an they worked great together. But to finish this off, "O Brother, Where Art Thou?" is a smart, funny, and a movie adventure that I wouldn't let pass up.