This dude is a former mailman from Maywood. I really should like his music, and I thought that I did for a little while—John Prine’s 1971 self-titled debut LP starts out pretty strong. “Illegal Smile,” a tribute to what I’m pretty sure is marijuana, gives the impression that the album is going to have at least a slight sense of humor. However, by the time “Hello In There” (the next track) rolls around, it becomes clear that this isn’t the case. What originally appeared to be a few lighthearted jokes take on whole different meanings, and it becomes evident pretty quickly that you’re in for one hell of a depressing ride.
Prine is unrelenting, as the very next song is centered on the line “there’s a hole in daddy’s arm, where all the money goes.”
Prine builds you up every now and then…however, he just ends up tearing you right back down. Tracks like “Paradise” and “Pretty Good” appear to be positive at first, but quickly take turns for the worst, as everything falls to pieces for Prine and his unfortunate characters.
This just kept happening and happening, and had I been in a different mindset, I might have loved it. However, I wasn’t really in the mood for music that makes it seem like there’s nothing good about life. Believe me, there are times when this record would be absolutely perfect, but that time ain’t right now.
With a weird voice and solid song writing, this record does have plenty of what I want out of my music. This album will probably come in handy down the road.
Swole Ear 
His songs are sad, but beautiful and real. I once saw him bring a grown woman to tears about three minutes into Hello in There. You’re right — you wouldn’t want to listen to him all the time, but there are moments when he’s perfect. Far better than Steve Goodman (another Chicago folk troubadour to whom he is often compared). Steve Goodman is famous because of an untimely death and a couple of novelty songs about the Cubs and country music. John Prine deserves his accolades.
J$, though I am far from an authority on Mr. Goodman, I am going to disagree. My Dad and Johnny Cash say Steve Goodman is alright. Plus he plays with Prine on this, my favorite version of one of Prine’s best songs: http://www.youtube.com/watch?v=aOTbg3-I
5MQr – and one of his most bittersweet .
Mr. Prine doesn’t care if he deserves our accolades because he has Johnny Cash, Bruce Springsteen, Kris Kristofferson, Bob Dylan, Bonnie Raitt, Billy Bob Thornton, Lucinda William and Emmylou Harris on his fanclub mailing list. Among others.
His album Bruised Orange is simply lovely. On it, he refers to Minnesota as “the land of the wind chill factor” which I know all of the above writers can appreciate. Its sad, but funny, kind of like Dr Chops. I might be able to direct you to a copy if you were so inclined.
…but you forgot to mention that Bruised Orange was produced by Steve Goodman.
Okay. I won’t hold against Steve Goodman those who have embraced him, even if they are drunken frat boy jags and worn out old radio djs who have not said anything funny or interesting in a generation. He did correspond with David Allan Coe, which weighs in his favor, but I guess I would rather listen to a David Allan Coe record if I had to choose. It doesn’t get much better than Would you Lay with Me (In a Field of Stone).
I was never in a frat!