When a film is based on Homer's 'Odyssey', it's gotta be good.
This is probably the only time I've been drawn to a movie because of the music. "Man of Constant Sorrow" was all over the place in 2000, which led me to pick up the entire soundtrack, which finally led me to watch the movie - I know, strange. The music is so interwoven into the story, that you can't have the movie without it.
The commentary on social and economic issues of the times is evident, some of which needs additional research to understand. I find myself picking up on new things every time I re-watch this one. I have no idea if this is an accurate representation of Mississippi during the Great Depression but it certainly a great way to get a small idea - from the overall look (which took a lot of digital alteration) to the dialogue of the era.
The excitement from the crowd and the subsequent look of bewilderment from the Soggy Bottom Boys as they sing their song near the end is great.