'Sundown'
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.
'Carefree Highway'
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.
'The Wreck of the Edmund Fitzgerald'
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.
'If It Should Please You'
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."
'Why not Give It a Try'
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.