Lyric discussion by chall85 

Cover art for Jim Cain lyrics by Bill Callahan

I think this song refers to his shift from Smog to Bill Callahan. In case things go poorly, i.e. his new solo work is a failure or he destroys his legacy, don't forget the good music from his past. The music of Smog also "does him in" because he may find it difficult to move out of the shadow of his earlier work.

My Interpretation