'O Brother, Where Art Thou?' (2000)

Clooney ventures into the 1930s -- make that Mississippi 1937 -- in Joel and Ethan Coens' quirky comedy, which is very, very loosely based on Homer's "Odyssey." Clooney won the Golden Globe for best actor in a comedy or musical for his outlandish, no-holds-barred turn as the fast-talking pomade-wearing con man Ulysses Everett McGill. He and his two buddies (John Turturro and Tim Blake Nelson) escape from a chain gang to retrieve a cool million that Everett says he buried before he went to prison for practicing law without a license. But the real reason he has escaped is to prevent his wife (Holly Hunter) from taking their kids and running off with another man.
Melinda Sue Gordon / Universal
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