O Brother, Where Art Thou?

O Brother, Where Art Thou? is the most audacious adaptation in comedy history — the Coen Brothers retold Homer's Odyssey as a Depression-era Mississippi road movie, and the result is a film so musical, so beautiful, and so deeply weird that it created an entirely new genre: the literary Southern comedy. George Clooney, in his first great performance, plays Ulysses Everett McGill, a pomade-obsessed convict on a quest to recover buried treasure before his wife remarries.

The film's soundtrack — produced by T Bone Burnett — sold eight million copies and won the Grammy for Album of the Year, single-handedly reviving mainstream interest in old-time American roots music. 'Man of Constant Sorrow' became a legitimate hit. The music is not background; it is the film's soul, weaving through every scene and connecting the Coens' absurdist humor to something ancient and genuine.

The Odyssey parallels are both faithful and hilarious. The Sirens washing clothes by the river. The Cyclops (John Goodman's Bible salesman with one eye). The suitors besieging Penny (Holly Hunter). The Coens claim they never actually read The Odyssey, which is either a lie or proof that Homer's story is so embedded in Western culture that you can retell it from memory. Either way, the film is a masterpiece of American comedy.