16. 'The Graduate' (1968)
Director Mike Nichols' brilliant use of several Simon and Garfunkel songs in his chronicle of post-collegiate alienation gave contemporary Sixties pop unprecedented placement in a serious Hollywood blockbuster. Longtime Miles Davis producer Teo Macero helmed the soundtrack, which was split between S&G songs from the film like "Mrs. Robinson" and "April Come She Will" and music by composer Dave Grusin (some of which, like the easy listening jazz-pop dollop "Sunporch Cha-Cha-Cha," is a kitschy good time). One song on the soundtrack but not the movie, "The Big Bright Green Pleasure Machine," is a loopy throwaway in which Simon's lyrics satirize a psychedelic advertising pitch, and the closing acoustic rendition of "Sound of Silence" is one of folk-pop's most beautiful moments.