John Prine recalled how his musical career began when he heckled performers at an open-mic night in the early ‘60s.

As a result of being dared to do better, the then-mailman found himself moving in the direction he’d always wanted to go, as he explained in one of the last interviews before his death last week.

“It was just a little club in Chicago, not even 20 people in there when I got up,” Prine told Mojo. “I wasn’t the type to heckle, but I’d had a few beers and wasn’t really impressed with what I was hearing and said so under my breath. And someone at the next table said, ‘Well, if it’s so easy, why don’t you get up and do it?’ So I said, ‘Well, maybe I will.’”

Prine remembered he "got up and sang ‘Sam Stone,’ and the audience just sat there. They looked at me, looked at each other, looked at me again … seemed like an eternity and finally they started applauding. The owner of the club came up afterwards and offered me a job singing there. I couldn’t believe it. The thing I really remember was that I was more comfortable than I’d ever felt. I just felt like that’s where I belonged.”

The buzz Prine soon created at the Fifth Peg folk club led to attention from movie critic Roger Ebert and country star Kris Kristofferson. Through Kristofferson, singer Paul Anka discovered Prine’s music too. “Anka wanted to manage me and [Steve] Goodman, so he ended up buying us plane tickets to New York,” Prine said. "I wasn’t gonna go, but Goodman talked me into it.

“We got to New York and picked up a copy of the Village Voice at LaGuardia [Airport], and we look at it, and Kris is playing at the Bitter End, and Carly Simon was opening. We took a cab on down there. Just as we got out, Kris and his band are walking down the street – they’d been at the bar next door between shows. Kris see us and says, ‘I’m gonna put you guys up onstage, you’re gonna do some songs tonight.’”

What Prine didn’t know was that they were about to take part in a showcase performance for music-industry representatives. “They were coming to see Kris ‘cause he was the new world wonder,” Prine noted. “It was full of label people. Jerry Wexler was sitting down front. He came and talked to me after I got offstage. Asked me to show up at his office at Atlantic at 10 the next morning. I showed up, and I had a record contract waiting for me. I hadn’t been in New York City 24 hours! If you’d put that in a movie, people would have thought it was too corny.”

Meanwhile, Roger Waters and Dave Matthews were among the artists who recently performed covers of Prine songs in tribute to him. You can watch Waters’ version of “Paradise” and Matthews’ take on “Speed of the Sound of Loneliness” below.

Enter your number to get our free mobile app

John Prine Through the Years