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 released 21 albums and numerous compilations, selling more than seven million records worldwide and earning a slew of awards, including 16 Junos and inductions into the Canadian Country Music Hall of Fame, Canada's Walk of Fame and the Songwriters Hall of Fame. Below are 10 songs that showcase how Lightfoot became one of the pioneering forces in Canada's music scene.

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This folk song was written by Lightfoot in 1964, but the seeds of inspiration for it were germinating years 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 song finally took shape.

The famous tune would go on to be covered by artists including Ian & Sylvia, Bob Dylan, Judy Collins and even rock star Elvis Presley.

Lightfoot released his debut album, Lightfoot!, in 1966, which included his single "Ribbon of Darkness." Although Lightfoot originally wrote the song and released it in 1965, it was covered that same year by Marty Robbins — and gave Robbins a No.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 song as part of a Lightfoot tribute album.

To commemorate Canada's centennial in 1967, Lightfoot penned what has become arguably one of his most iconic songs of all time. "The Canadian Railroad Trilogy" was commissioned by CBC for a New Year's Day broadcast, and mentions the Rockies, the Prairies and Gaspé. Through his vibrant lyrics, Lightfoot details the majestic beauty of nature and the climactic construction of the 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" won a special award from the Canadian Railway Hall of Fame in 2003, and seven years after that it was transformed into an illustrated book.

In July 1967, the Detroit race riots began after a police raid of an illegal after-hours drinking club. The resulting protests and confrontation between the city's Black residents and the police force lasted five days, and resulted in 43 deaths and numerous injuries. Lightfoot wrote "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 released around the 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.

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 later on 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 including Barbra Streisand, Olivia Newton-John, Kenny Rogers, Liza Minnelli, Johnny Cash and Stars on 54 putting their spin on the ballad.

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

The title track of Lightfoot's 1974 album was another of his biggest hits, and he wrote it about his girlfriend at the time, Cathy Smith. While wondering what Smith was doing while out at a bar with her friends, Lightfoot started crafting the song at home. He explained to American Songwriter that 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.

Another of Lightfoot's chart-toppers from his 1974 album was "Carefree Highway." He composed the song while driving in a rental car through Arizona with his bassist, as he told Mass Live about 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.'" Lightfoot wrote the words down 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 about a failed romance with a woman named Ann — although he said it was written while wondering if his relationship with his girlfriend at the time would last.

Lightfoot's sombre 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 killed all 29 crew members. Lightfoot learned about the incident from a Newsweek article and wrote the song, which was released in 1976.

"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," Lightfoot told 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.

Lightfoot's 1988 album, Gord's Gold, Vol. 2, was a compilation that included re-recordings of hits such as "The Wreck of the Edmund Fitzgerald." The first track on the album, though, was a new one called "If It Should Please you," and the country-tinged song was one that Lightfoot often performed live but had not been previously recorded. With a catchy, dulcet melody, 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 classics in his catalogue, Lightfoot showcased the true breadth of music in his arsenal with the recording of "If It Should Please You."

Lightfoot was still churning out new music in his 80s, and in 2020 released his 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 Sound about 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's first album in 16 years, and "Why not Give It a Try" the closing track. It was the final bow 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.