I've been after this CD for a while and finally got it for a Christmas present, but I have to say that it didn't match my expectations. I hadn't heard anything else by Jack, but bought it on the basis of his friends. With accompaniment by the likes of Arlo Guthrie, Peter Rowan, Norton Buffalo, Emmylou Harris, Tom Waits, Nanci Griffith, John Prine, Guy Clark, and Bob Weir (amongst many others) how could it possibly fail?
Unfortunately there are several ways in which it fails to hit the spot for me. The first is that some of the songs are weak (particularly Me & Billy the Kid and Bleeker Street Blues). Many of the songs are covers which have been performed better elsewhere - Friend of the Devil and He Was a Friend of Mine are both particularly poor in comparison to other versions.
It's also self-indulgent. Before starting a couple of the songs, Jack indulges in a bit of banter with one or other "friend". This adds nothing to the music, and will grow increasingly tedious the more you hear it.
There are some pluses, and for me the stand-out track is Dark as a Dungeon - a song about coal miners with Guy Clark sharing guitar and vocal parts.
Overall, though, the feel of the album is rather sad. It smacks to me of an artist who is past his prime (at least on the vocals) and maybe has financial problems. Accordingly he has rustled up as many of his famous friends as possible to make an album with him which will sell largely on the basis of his friends.
Interestingly the All Music Guide describes this as "thoroughly enjoyable" but gives it only 3 stars out of 5. On Amazon.com you'll find (at the time of writing) seven reviews, three 5-star, three 4-star, and one 3-star. So maybe I've got it all wrong.