I Hope It Rains At My Funeral
"I Hope It Rains At My Funeral" is one of his more under-rated songs. It's really a very sad song, but he sings it in his kinda sing-songy manner. Whiskeytown, before the split and subsequent douchery, covered this on a tribute album and it is amazing.

Fallen Angel
A great documentary to watch is "Fallen Angel." It fits the format of most musical documentaries, but its a great watch. I ended up watching it and then becoming a fan of his music. He lived a crazy life that only privilege would enable, but I can't blame him.