I have always loved the soundtrack from "Newsies."
Very good song selection for a movie was in Donnie Darko. It's full of 80s pop music and such, only there is no soundtrack, just a score. One of the best fitting songs i have ever heard in connection with a movie was for this film with the song "Mad World" by Gary Jules. It's amazing.
It is basically the tale of my DH and I. We were just friends for many years while we each dated other people, and he would ask over and over if I ever thought something would change between us. I would always respond by saying he was my "Harry" friend. Things eventually changed and I realized that my feelings were changing and on New Years Eve 1994(95) we had our first kiss
4 months later as the credits were rolling on this movie, he asked me to marry him, and our first dance at our wedding was "It Had To Be You"