14. 'Easy Rider' (1969)
Dennis Hopper selected songs for Easy Rider based on stuff he was hearing on the radio in 1968. He came up with a groundbreaking album that included biker-rock from Steppenwolf, pastorale country-rock from the Byrds and the Jimi Hendrix freak-power anthem "If 6 Was 9." When the low-budget hippie road epic became a surprise blockbuster, the freewheeling flow of the music in the film became a huge part of its success and myth. Wisely, the songs on the soundtrack were sequenced the same way they appear in the film. That Dennis – what a DJ.