Old Joy is a 2006 American road movie written and directed by Kelly Reichardt and based on a short story by Jonathan Raymond.[3] The original soundtrack for the film is by Yo La Tengo and included on the compilation soundtrack album They Shoot, We Score.
https://en.wikipedia.org/wiki/Old_Joy
I’ve never seen (or heard of it until) now, but Will Oldham may also be known as the musician Bonnie ‘Prince’ Billie. Will give it a watch sometime.