I was thinking more in terms of lyrics covering real life experiences. AO really wears his heart on his sleeves (or jeans) when singing about his struggles with addiction. I'd recommend giving a listen to his American Patchwork album, or better yet, just "When Will I See You Again," from his latest CD.
I've never seen him live, but I heard he puts on a good show. Many critics claim he deserves more recognition. I could picture AO and BF having a long conversation over coffees.
"One Step At A Time" is another good song he did with Mike Zito - YouTube it - it's a good one.