Lyric discussion by chall85 

Cover art for Jim Cain lyrics by Bill Callahan

This interview from Pitchfork in 2007 should give you an idea of what this song is about, in my opinion.

Callahan: I cannot tell you exactly what is going on now. I look at my hands and I don't know what they wrought in the past. Are they the hands of a bad man? I used to be an artist. I don't think I am right now. I don't know if I ever will be again. I am something else. I was a student of personal strife. I ran with the wrong crowd early on. I tortured myself for a song. I thought it was the way.