I'm pretty sure this has not been mentioned: the soundtrack to The Mission is unbelievable (it's Ennio Morricone).
Also, I'm a big Elliot Smith fan, so I've got to give it up to Good Will Hunting.
Others I really like: Swingers, Philadelphia, I am Sam (all Beatles by different artists), Jerry Maquire and Dan in Real Life (Sondre Lerche is [dang] good).
Agreeing with a bunch of others on Garden State, Reservoir Dogs, Trainspotting and Tejada Dey Come.