Gordon Lightfoot's life in 10 songs

Award-winning singer-songwriter Gordon Lightfoot died on May 1, 2023, aged 84, ending a career that spanned more than five decades and included honours such as the Order of Canada and an induction into the Canadian Music Hall of Fame.

Lightfoot once called songwriting "15 per cent inspiration and 85 per cent perspiration," and penned iconic hits including "If You Could Read my Mind" and "Sundown." His musical catalogue is rich with songs that help illustrate his journey from a burgeoning Orillia-born talent to one of Canada's greatest musicians.

A veteran performer into his 80s, Lightfoot helped shape the canon of folk music with his heartfelt and historical songs that touched so many. He released21 albums and numerous compilations, selling more than seven million records worldwide and earning a slew of awards, including 16 Junos and inductions intothe Canadian Country Music Hall of Fame, Canada's Walk of Fame and the Songwriters Hall of Fame. Below are 10songs that showcase how Lightfootbecameone of the pioneering forces in Canada's music scene.

WhichLightfoot songs would you add to this list? Let us know on Instagram @cbc_music.

'Early Morning Rain'

This folk song was written by Lightfoot in 1964, but the seeds of inspiration for itwere germinatingyears prior, according to an interview with American Songwriter. While watching airplanes on a rainy day, Lightfoot recalled the imagery of "an airplane climbing off into overcast," and five years later while watching his first-born child, the songfinally took shape.

The famous tune would go on to be covered by artists including Ian &Sylvia, Bob Dylan,Judy Collinsand evenrock starElvis Presley.

'Ribbon of Darkness'

Lightfoot released his debut album,Lightfoot!,in 1966, which included hissingle "Ribbon of Darkness." Although Lightfootoriginally wrote the song and released it in 1965, it was covered that same year by Marty Robbins and gave Robbins aNo.1 hit on the U.S. Country Singles chart. Despite the song's cheerful melody and bright whistling, Lightfoot's lyrics told the melancholy story of a lost lover: "Oh how I wish your heart could see/ how mine just aches and breaks all day."

In later years, Connie Smith, Jack Scott and Bruce Cockburn also covered "Ribbon of Darkness," with the latter recording the songas part of aLightfoot tribute album.

'The Canadian Railroad Trilogy'

To commemorate Canada's centennial in 1967, Lightfoot penned what has become arguably one of his mosticonic songs of all time. "The Canadian Railroad Trilogy" was commissioned by CBC for a New Year's Day broadcast, and mentionsthe Rockies, the Prairies and Gasp. Through his vibrant lyrics, Lightfoot detailsthe majestic beauty of nature and the climactic construction ofthe Canadian Pacific Railway: "For they looked in the future and what did they see?/ They saw an iron road runnin' from the sea to the sea."

"The Canadian Railroad Trilogy" wona special award from the Canadian Railway Hall of Fame in 2003, and seven years after thatit was transformed into an illustrated book.

'Black Day in July'

In July 1967, the Detroit race riots began after a police raidof an illegal after-hours drinking club. The resulting protests and confrontation between the city'sBlack residents and the police force lasted five days, and resulted in43 deaths and numerous injuries. Lightfootwrote "Black Day in July" to recount the bloodshed,with vivid lyrics illustrating the destruction: "And the people rise in anger and the streets begin to fill/ and there's gunfire from the rooftops and the blood begins to spill."

"Black Day in July" was releasedaroundthe same time as the assassination of civil rights activist Martin Luther King Jr. in 1968,causing many radio stations in America to ban the song.

'If You Could Read My Mind'

One of Lightfoot's biggest hits was the heartbreak-driven "If You Could Read My Mind," which was inspired by the dissolution of his first marriage. The song was written in 1969 and released a year lateron the album of the same name, hitting No. 1 on the Canadian Singles chart. Covers of the song spanned genres from country to disco, with musicians includingBarbra Streisand, Olivia Newton-John,Kenny Rogers,Liza Minnelli, Johnny Cash andStars on 54 putting their spin on theballad.

The song also shares atitle with the 2019 documentaryGordon Lightfoot: "If You Could Read My Mind,"directed by Martha Kehoe and Joan Tosoni. The film earned a Canadian Screen Award nomination in 2020.

'Sundown'

The title track of Lightfoot's 1974 albumwas another of hisbiggest hits, and he wrote itabout his girlfriend at the time, Cathy Smith.While wondering what Smithwas doing while out at a bar with her friends, Lightfootstarted crafting the song at home.He explained to American Songwriterthat he thought the track resonated with fans because it had "a good beat," "interesting harmonic passages" as well as"a great arrangement and not too bad of a vocal."

Lightfoot's relationship with Smith was reportedly sometimes violent, and the lyrics illustrate the dark nature between the pair:"She's a hard-loving woman, got me feeling mean."

"Sundown" has been covered by musicians including Toby Keith and Depeche Mode.

'Carefree Highway'

Another of Lightfoot'schart-toppers from his 1974 album was"Carefree Highway." Hecomposed the song while driving in a rental car through Arizona with his bassist, as he toldMass Liveabout the inspiration:"All of a sudden, this sign went flashing by. It said, 'Carefree Highway.'And I looked at the bass player and he looked at me, and I said, 'That must be, like, a title of a song.'" Lightfootwrote the wordsdown on a page of the rental contract and tucked it away in his wallet. After finding the scrap of paper two weeks later,he wrote "Carefree Highway," which he turned into a song abouta failed romance with a woman named Annalthoughhe said it was written while wondering if his relationship with his girlfriend at the time would last.

'The Wreck of the Edmund Fitzgerald'

Lightfoot'ssombre hit "The Wreck of the Edmund Fitzgerald" was inspired by the sinking of the bulk carrier S.S. Edmund Fitzgerald on Lake Superior in 1975, a tragedy that killedall 29 crew members.Lightfootlearned about the incidentfrom aNewsweek articleand wrote the song, which was released in1976.

"It's just one of those songs that just stands the test of time and it's about something that, of course, would be forgotten very shortly thereafter, which is one of the reasons I wrote the song in the first place. I didn't want it to be forgotten," Lightfoottold the Milwaukee Journal Sentinel about immortalizing the wreck in song.

"The Wreck of the Edmund Fitzgerald" hit No.1 on the Canadian charts, was nominated for two Grammy Awards and was covered by artists including the Dandy Warhols, Tony Rice and more.

'If It Should Please You'

Lightfoot's 1988 album,Gord's Gold, Vol. 2, was a compilationthat included re-recordings of hits such as "The Wreck of the Edmund Fitzgerald." The first track on the album, though,was a newonecalled"If ItShould Please you," and the country-tinged song was one thatLightfoot often performed livebut had not been previously recorded. With a catchy, dulcetmelody, the track demonstrated what audiences could expect from Lightfoot in concert:"So I'm itching to please you, with a topical song/and a few golden oldies and a little hoedown." With all the classicsin his catalogue, Lightfootshowcased the true breadth of music in his arsenal with the recording of"If It Should Please You."

'Why not Give It a Try'

Lightfoot was still churning outnew music in his 80s, and in 2020releasedhis first-ever solo recordings."I actually tried for several months to orchestrate these tracks and I even tried rewriting five or six of the songs," he told the Absolute Soundabout the aptly titled album,Solo."Finally, I decided these tracks were fine, since they were recorded before any of my health issues. We listened to them again as solos and decided we couldn't make them sound any better."

Solo was Lightfoot'sfirst album in 16 years, and "Why not Give It a Try" the closing track. It was the finalbow on his 21st album;a simple ode to experimenting with new things, whether it be dancing,travel or staying true to oneself. "Would you like to go dreaming, would you like to go free?" he sings, stripped-back and simple with just voice and guitar.

"This one is special; it's a really good one, but it's as different as it's ever going to get," he told the Toronto Star.