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The remarkable moment John Prine first met Bob Dylan in New York City


They say New York City is a place of dreams. As the American poet Dorothy Parker once wrote: “London is satisfied, Paris is resigned, but New York is always hopeful. Always it believes that something good is about to come off, and it must hurry to meet it.” Not everyone would agree with that, but John Prine found it to be pretty much that exactly. In his first week there he was invited to Carly Simon’s apartment where he met his hero, Bob Dylan. Now that’s proof of a city rushing at a comical pace.

As it happens, a healthy dose of showbiz fate always seemed to reside over the least showbiz singer-songwriter’s career. At the beginning, Prine recognised that his own songs were so unique he was almost fearful to play them. “Some were so different that I hesitated to sing them for anybody because I thought I hadn’t heard anything like this before, like ‘Sam Stone’. And I thought, ‘Is it because it’s really good, or is it because it’s so awful?’”

Fortunately, fate encouraged him to put his hesitancies to one side one evening and play his singular songs in a basement bar. “Through no wisdom of my own but out of sheer blind luck,” the late movie critic Roger Ebert wrote on his website, “I walked into the Fifth Peg, a folk club on West Armitage, one night in 1970 and heard a mailman from Westchester singing. This was John Prine.”

Adding: “He sang his own songs. That night I heard ‘Sam Stone’, one of the great songs of the century. And ‘Angel from Montgomery’. And others. I wasn’t the music critic for the Chicago Sun-Times, but I went to the office and wrote an article. And that, as fate decreed, was the first review Prine ever received.”

As it turned out, Ebert had been paid to review a film that fateful night; however, the picture was so bad that he couldn’t bring himself to sit through the whole thing. He waltzed from the cinema into the rainy night and began looking for a beer to cut through the lingering taste of bad popcorn and worse acting. He popped into the Fifth Peg and heard John Prine perform. He was so moved by the performance that he slipped from celluloid to songbook to pen an impassioned review. 

His piece in the Chicago Sun-Times, from the 9th of October 1970, ran with the headline: “Singing mailman who delivers a powerful message in a few words.” Therein Ebert describes the lyrical genius and stirring performer, John Prine, whom he witnessed purely by chance. And with that, the pandora’s box was open and the brilliance of Prine was never going back inside. 

About ten years earlier, Dylan had been swamped out by the ubiquity of would-be folk stars who had descended onto the beat streets of Greenwich Village. The issue was the bohemian New York suburb was literally swarming with, well, fellow bohemians. There was a regional shortage of flannel, whisky and good fortune. Thus, you had a thousand artists playing the same songs in the same basement bars on the same nights, like some rolling Groundhog Day of whining “fat people” as Dylan once put it himself.

Thus, in 1961, Dylan hounded down his own esteemed critic named Robert Shelton. The New York Times reporter had witnessed Dylan at a few house parties and always loved his unique style, but he was also always aware that he could hardly post a spread in a paper as revered his about a house party show. Thus, he resisted Dylan’s nagging. 

Fortunately, Dylan acquired a two-week opening slot for the bluegrass troupe, The Greenbriar Boys, at the hallowed venue Gerde’s Folk City. This was Dylan’s biggest show to date, and it convinced Shelton that this was the right moment to afford him the review. He wrote: “Resembling a cross between a choir boy and a beatnik, Mr. Dylan has a cherubic look and a mop of tousled hair he partly covers with a Huck Finn black corduroy cap. His clothes may be in need of a bit of tailoring, but when he works his guitar, harmonica or piano and composes new songs faster than he can remember them, there is no doubt that he is busting at the seams with talent.”

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A decade on, Dylan’s talent had changed the world forever and Prine was the new kid on the block with a hot review in his pocket. “I got to New York and me and [Steve] Goodman picked up a Village Voice and saw that Kris [Kristofferson] was playing at the Bitter End… So, we said, ‘Hey let’s go straight down there’. It was like one of those old B-movies we had our little suitcase and our guitars,” Prine once said. 

After the show, Prine’s pal Kristofferson said why don’t you come across town to Carly Simon’s apartment. So, they went over and then there was a knock at the door, and it was Bob Dylan, of all people! At the time he was still on hiatus after his motorcycle crash. “We got introduced and pretty soon the guitars came out. I got to singing one of my songs called ‘Far From Me’. My first album was three weeks away from being released and all of a sudden Bob Dylan starts singing along.”

This came much to Prine’s surprise considering his record hadn’t even been made public yet. Somehow word had got out about Prine’s brilliant new record amid the industry and someone had sent Dylan a copy—Dylan approved. “I’m sitting there thinking, ‘I know all your songs, but how do you know mine!’” an awestruck Prine recalls. 

Three weeks later, Dylan even broke from his musical hiatus to play the harmonica with Prine and Goodman. Prine recalls introducing him, “and about three people cheered because they figured I was just joking around.” He certainly wasn’t, Dylan described Prine’s songs as “Midwestern mind-trips to the nth degree,” endorsed them glowingly, and the rest is ancient history.

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