O Brother, Where Art Thou? (2000)
Depression era American South is given the Odyssey treatment in this crafty, beautifully shot and at times enjoyable fable from the Coen brothers. The film looks to have been a lot more fun shooting than it is watching. It's got an unmistakable meta-level quality to it that makes it almost impossible to dive into – except strictly intellectually. It's a film which appeals more to your senses than your sensibilities. The story plays out as constructed as you'd expect from a reinterpretation of Homer's The Odyssey, but there are abundances of fine observations of bygone customs and mannerism which in particular will please those who remember them. The star of the show, however, is the soundtrack, which consists mainly of bluegrass and folk music from the relevant era, produced by T-Bone Burnett, most notably the unlikely hit "Man of Constant Sorrow".