1. Buena Vista Social Club (1999)
The ultimate example of a film that made history as well as recording it, Ry Cooder’s semi-Quixotic mission to track down musicians from the fictional Buena Vista Social Club (with German director Wim Wenders of Paris, Texas fame in tow) is not only a giant of a movie but it resulted in one of the great albums of the ’90s and an unlikely crossover success for authentic Cuban roots music. The whole damn thing is watchable on YouTube. Get a sample above and then proceed here.