How Heartbreak Led John Prine to Songwriting, Revenge, & To His Hero, Gordon Lightfoot

John Prine didn’t need much to tell a great story. He just needed a guitar, a sharp line, and something worth saying. And when it came to songwriting, he had nothing but respect for the people who did it right. One of those people? Gordon Lightfoot.

They weren’t a writing duo, and they didn’t need to be. Their friendship was simple: mutual admiration, a few nights out, and a long-running appreciation for each other’s craft.

Prine once shared the story of how he wrote “Far From Me,” one of his earliest and most biting breakup songs, and there was a little confusion at what “get her back” meant when a fan asked if it worked:

“I wrote this song to get her back… No, I mean revenge. I wanted revenge.”

Then came the kicker:

“Revenge is a really good songwriting weapon.”

He also credited this mystery woman as the reason he wanted to become a songwriter (heartbreak will do that to you).

That was back in 1971, when Prine was playing The Riverboat Coffee House in Toronto, a tiny venue that somehow managed to book the best songwriters in the world before they blew up. Simon & Garfunkel, Tim Buckley, Kris Kristofferson, Steve Goodman, James Taylor. And a young John Prine playing three or four nights a week, finding his voice.

On his second night at the Riverboat, Gordon Lightfoot walked in.

“My songwriting hero”

That moment meant something. Later, they had a few beers and hung out like they’d known each other for years. Years later, Prine told that story onstage before playing Far From Me live.

“You were standing in the middle of Yonge Street singing the chords to this. So this is for you, Gordon.”

Then he played the song. It’s quiet, understated, and sharp. A gut-punch wrapped in plain language:

“Ain’t it funny how an old broken bottle, looks just like a diamond ring?”

Lightfoot was in the crowd that night, sitting still, mouthing the lyrics to himself. No spotlight, no dramatic reaction. Just one songwriter hearing his friend tell the story again, maybe for the hundredth time, but it seemed to never lose its value.

It wasn’t some overblown emotional moment. It was just two guys who understood each other and what it meant to put pain into a song that lasts. No label. No forced nostalgia. Just a moment that hit, and stuck around. The kind of thing that reminds you why people keep coming back to songs like these in the first place.