I found these excellent video tributes to pop culture by the decade.
I would say they tend to draw too much from the same sources (e.g. the 1980s one has about ten clips each from Aliens and The Breakfast Club and not one from Nightmare on Elm Street or Return to Oz), but the editing and the way they time the clips to the music is fantastic.
1950s
(By the way, the clips of Dean Martin and Jerry Lewis always bring a lump to my throat, since it makes me remember an interview with Lewis near the end of his life where, to the question what he missed most about his career, answered “When my partner was alive.”)
1960s
1970s
1980s
1990s