O Brother Where Art Thou?
- Awards: 2 Grammy Awards, 2 Oscar & Golden Globe Nominations
George Clooney had been part of other movies by this point and even had a memorable stint on the E.R. TV series. But O’Brother Where Art Thou put him in another stratosphere. Loosely based on Homer’s Odyssey, this film takes place in 1937 Mississippi during the Great Depression. The story itself follows Ulysses Everett McGill, Delmar O’Donnell, & Pete who escape a prison chain gang. They end up becoming a singing group known as the Soggy Bottom Boys and somehow become a musical hit. This movie’s soundtrack actually won the 2002 Album of the Year at the Grammy Awards. It is the only film soundtrack in history to ever do this.