Being from Chicago, I first saw Prine when he was a young folkie. He gained attention as a good friend of Steve Goodman's.
A good anthology of that scene, with songs by Chicago artists including Prine, and guests such as Bonnie Raitt, Arlo Guthrie, Jethro Burns, Richie Havens, David Bromberg, etc., is the live album of the tribute concert after Goodman's untimely death.
[
www.amazon.com]