Grease!
Ballad of Thunder Road - Robert Mitchum from the movie Thunder Road.
Gay.
Glad I didn't say 'An Officer and a Gentleman' with 'Up Where We Belong'
Donnie Darko - dunno what the song is called but it worked great.
For purely personal reasons:"Angel Band"; from O Brother! Where Art Thou?"
This one?http://www.youtube.com/watch?v=DR91Rj1ZN1M