O Brother, Where Art Thou? (2000)
The first time I tried to watch this movie, I turned it off after 5 minutes. I didn't realize it was a comedy and went on to watch something else. I loaded it up later, months later, and was pleased when I finally discovered it really was a comedy.
This is the story, loosely based on Homer's epic poem "The Odyssey", of three escaped convicts trying to find a treasure. It's set in the 1930's deep south, during the depression era, and was filmed in colors that would remind someone of that era. I'm not into country music, but I actually enjoyed "I Am A Man Of Constant Sorrow", which is featured in the movie.
Starring George Clooney, John Turturro, Tim Blake Nelson, John Goodman and more. Here's a music video which shows clips from the movie:
