I was introduced to Aimee Mann when I first watched Magnolia years ago. I bought the soundtrack based on her songs. It's embarrassing to say but her songs were a comfort to me. She seemed to take the side of the lonely man, and it was reassuring to listen to her music every once in awhile. Not a lot of female artists I've encountered take that side as clearly as she has.
This isn't turning into a music forum, and I'm not trying to wallow in self-pity with these sad songs.