The lesser known histories behind 5 Gordon Lightfoot songs

Gordon Lightfoot’s prolific songs are likened to anthems in Canada.

He penned more than 500 of them, each one telling an honest story, both personal and universal, paired with the “chime of his twelve-string guitar and the iconic timbre of his voice,” Jesse Kumagai, President and Chief Executive Officer of Massey Hall, told CTV News Toronto.

On Tuesday, Lightfoot died at 84. He made more than 170 appearances at the historic Toronto venue.

“The world has lost one of its most profound voices, but his songs will play on and his soul will always be found at Massey Hall,” Kumagai said.

Lightfoot’s biographer, Nicholas Jennings, chose five of the musician’s songs and told CTV News Toronto about their histories.

Early Morning Rain

In 1964, Lightfoot wrote “Early Morning Rain” – a song that remains one of his top hits to this day.

Lightfoot studied jazz composition at a college in Los Angeles, CA., but often felt homesick for Orillia, Ont. On such days, he is said to have gone to the airport to watch the planes take off.

The song contains what Jennings considers one of Ligthtfoot’s best lyrics: “You can't jump a jet plane like you can a freight train.”

“That’s a very clever confluence of the past and present, or the past and modern times, and yet really what he is conveying in that song is this deep longing,” Jennings said.

This old airport's got me down, it's no earthly good to me

And I'm stuck here on the ground as cold and drunk as I can be

You can't jump a jet plane like you can a freight train

So, I'd best be on my way in the early morning rain 

Summer Side of Life

Jennings points to “Summer Side of Life” as a testament to Lightfoot’s unparalleled storytelling ability to tell a narrative that feels detailed and specific, yet relatable.

“What’s powerful for me about that song is he is really contrasting the innocence of youth with this young man who is in love and seeing his girlfriend, yet hanging over him is the incredible wait that he has signed up for,” Jennings said.

The song is about an American soldier leaving home to fight in the Vietnam War.

And if you saw him now

You'd wonder why he would cry

The whole day long

“It’s a contrast of innocence and the hard realities of life, even if you dont know it’s about the Vietnam War.” 

The Pony Man

Lightfoot wrote “The Pony Man” for his children in 1970, a fantastical bedtime story fused with a lullaby.

The images he illustrates with his words – of a pony who lives on “candy apples instead of oats and hay” – are reminiscent of tales like Peter Pan and Willy Wonka.

And then we form in single file, inside the moon we go

Into a land of magic that the grownups do not know

Where the streets are paved with chocolate and the trees are hung with toys

And there's chewing gum for every one of the little girls and boys

“This is the only one he specifically wrote for children,” Jennings said.

“It’s a song that I think just transcends time. It could be a children’s song today, yet he wrote it in the early 70s.”  

Oh, Linda

“Oh, Linda” appeared in the musician’s debut album in 1966.

It was also the first – and last – time Lightfoot wrote and recorded a song without his guitar, Jennings said.

The acoustic jazz swing, only accompanied by Spike Lee’s father Bill on the bass, is about Lightfoot saying goodbye to a woman who mistreated him.

Oh Linda you made me grieve

I feel like I could die

Look out baby the moon is falling

Down from your sky

As for why he chose this song to be his solo acapella track, Jennings said he never asked Lightfoot, and the singer never said. 

Oh So Sweet

“Oh So Sweet” was one of the last songs Lightfoot ever wrote, released in 2020.

“It’s just him and his guitar, wonderfully raw and unvarnished and therefore, I think the emotion of his songs really, really comes through. It’s almost like him baring his soul by not having any accompaniment,” Jennings said.

Sometimes I remember hearin' raindrops fall

Feelin' my love breathing alongside of me

It ain't easy to live with no tears of regret

But sometimes it was, oh, so sweet

Much of the album, Solo, is a bittersweet lookback on his life, wondering whether he did the best he could – “that’s who Gordon Lightfoot was,” Jennings said.