How Roger Ebert Discovered John Prine In 1970, Ebert was a young critic at the Sun-Times, when he came across a young singer-songwriter-mailman playing future standards at the Fifth Peg, in “out of the way” Lincoln Park.

In one of those wonderful Chicago moments, it turns out that one of the best writers to ever come out of the city discovered, or was at least the first person to review, one of the best musicians to ever come out of the city: Roger Ebert covered John Prine for the Sun-Times in 1970, back when he was still a mailman and playing at the Fifth Peg, “out of the way” at 858 W. Armitage, a couple blocks from where Charlie Trotter later redefined Chicago cuisine. Ebert’s original review is, as you’d expect, great. What surprised me about it was how many of Prine’s masterpieces had already been written (coincidentally, Ebert’s piece ran on October 9, the day before Prine turned 24): “Illegal Smile,” “Angel From Montgomery,” “Sam Stone” (then “The Great Society Conflict Veteran’s Blues"), “Your Flag Decal Won’t Get You Into Heaven Anymore.”

Prine was also a child of one of my favorite Chicago subjects, the Hillbilly Highway, though I didn’t know how good his pedigree was:

So you talk to him, and you find out that Prine has been carryng mail in Westchester since he got out of the Army three years ago. That he was born in Maywood, and that his parents come from Paradise, Ky. That his grandfather was a miner, a part-time preacher, and used to play guitar with Merle Travis and Ike Everly (the Everly brothers’ father). And that his brother Dave plays banjo, guitar and fiddle, and got John started on the guitar about 10 years. ago.

Paradise, in western Kentucky, no longer exists. Coal companies strip mined the land around it, and residents sold out to the TVA to escape the massive Paradise Fossil Plant.

Here’s Prine playing my favorite of his songs, “Sabu Visits the Twin Cities Alone,” eight years out from Ebert’s piece.

And “The Late John Garfield Blues", from 1972:

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