Let’s take "Midnight Cowboy," a great film (based on the homonymous novel written in '65 by James Leo Herlihy) from '69, directed by John Richard Schlesinger, and you can find a little bit of everything in it, including two independent debuts:
1. the first film starring Jonathan Vincent "Jon" Voight as the lead alongside the legendary Dustin Hoffman.
2. the first album "Wanted Dead or Alive" released by Warren Zevon, from which the song "She Quit Me," composed, performed, and sung by him, is taken.

It won as many as 3 Academy Awards, including one for "Best Director" awarded to the legendary John Schlesinger.

Warren Zevon - She Quit Me - From the movie "Midnight Cowboy", 1969.