Acceptably, O Brother, Where Art Thou? and Death Proof. Probably less acceptably, Juno and Definitely, Maybe. The score for another Coen Brothers film, Raising Arizona, is very cool. Deliverance is worth watching just for "Duelling Banjos". And, I guess Almost Famous has a pretty good soundtrack - and Dazed and Confused works, even if I don't like all the songs in themselves. Best scores are by John Carpenter and Ennio Morricone - The Untouchables is amazing. Oh, and I have a residual fondness for Ash's cover of "Cantina Band" from Star Wars.
As for TV shows, I would say The West Wing. Yes, I'm biased as it's my favourite show, but they make the best possible use of Jeff Buckley's "Hallelujah" cover, and they have amazing versions of "Shed a Little Light" (James Taylor) by Aimee Mann and "A Change is Gonna Come" (Sam Cooke) by James Taylor. Plus they use Ryan Adams ("Desire", from the underrated Demolition album). I always liked ER's music choices as well, and though I didn't watch the show religiously, it was cool that Friends used Jefferson Airplane at the end.