The 10 Best Gordon Lightfoot Songs of All-Time

Gordomn Lightfoot

If anyone knows how to weave a tale, it’s Gordon Lightfoot. The Canadian singer-songwriter has been entertaining and enthralling us with his songs for more than six decades, and looks in no danger of stopping anytime soon. A folk-rock legend, he’s been described by Robbie Robertson of the Band as a “national treasure” and by Bob Dylan as one of the greatest ever songwriters. Here’s our pick of the best Gordon Lightfoot songs of all time.

10. Oh So Sweet


Lockdown didn’t come with many pleasures, but it did give us Solo. Released in March 2020, Lightfoot’s latest album proves he can sing just as well as he could back in his heyday. It’s a highlight is Oh So Sweet, a song that describes as “the ballad of Gordon Lightfoot,” an emotive retrospective that finds Lightfoot looking back on his life and concluding “Wasn’t it good, wasn’t it bad? Or the best you ever had? But sometimes it was, oh, so sweet”.

9. Carefree Highway


Next up is Carefree Highway, a delightful little number that, according to Wikipedia, uses “Carefree Highway” as a metaphor for the state of mind where Lightfoot seeks escape from his thoughts of a long-ago failed relationship with a woman named Ann. Lightfoot has since explained that Ann was actually a real woman with whom he had a brief but devasting fling when he was 22. “It was one of those situations where you meet that one woman who knocks you out and then leaves you standing there and says she’s on her way,” he’s explained. Released as the second single from his 1974 album, Sundown, it soared to No. 10 on the Billboard Hot 100 and topped the Easy Listening chart.

8. Early Morning Rain


Lightfoot has often cited Early Morning Rain as one of his all-time favorite songs. Although he wrote the song in 1964, it was actually inspired by his time in Westlake, Los Angeles, in 1960. Whenever Lightfoot felt homesick, he would visit Los Angeles International Airport on rainy days to watch the planes coming into land. A few years later, he was looking after his then 5-month-old son when he suddenly decided his memories of the experience would make a good song. He was right. Since its release, Early Morning Rain has been covered by numerous artists, including Ian & Sylvia, Peter, Paul, and Mary, and the Grateful Dead, but the original still has the edge.

7. Dream Street Rose


As notes, the title cut from Lightfoot’s 14th studio album found the singer in fine musical form. Everything hits the right note, from the gentle chug of the guitar to the uplifting vocals. Written about the positive impact the right person can have on your life, it’s as warm and comforting as a summer’s breeze.

6. Rainy Day People


In 1975, Lightfoot scored a major hit with Rainy Day People, a movingly tender song about how certain people might not call you every day, but are still there for you when you need them. Released on his 11th original album, Cold on the Shoulder, it became his fourth No.1 single on the Easy Listening chart, as well as a No. 26 hit on the Billboard Hot 100.

5. Ribbon Of Darkness


In 1965, Marty Robbins hit the No. 1 spot on the Hot 100 with Ribbon of Darkness. A few years later, Connie Smith scored a top 20 hit on the country charts with her version. Both were good, but neither quite match up to the perfection of Lightfoot’s original. Released as a single in 1965 and included on his debut album Lightfoot! a year later, it pitches country against pop and comes up fighting. Almost 40 years later, Canadian singer-songwriter Bruce Cockburn paid his respects to the song with a stirring rendition for the 2003 tribute album, Beautiful: A Tribute to Gordon Lightfoot.

4. Ode to Big Blue


Lightfoot’s 8th original album, Ode to Big Blue, has it all. His trademark folk sound is still very much in evidence, but there’s enough variety (the seafaring Christian Island and the protest song The Patriot’s Dream, for example) to keep us on our toes. The entire thing is golden, but Ode to Big Blue stands out as one of its most exceptional offerings. Basically, it’s a ballad about the life of a whale, which may sound a bizarre choice of subject material, but bizarre can sometimes be beautiful. Here, it’s practically transcendent. If you didn’t think hearing about the battle scars of a big fish could be interesting, a few minutes of this will set you right.

3. If You Could Read My Mind


By 1970, Lightfoot was a big name in Canada but a relative unknown in the US. Then along came If You Could Read My Mind, and suddenly, Gordon Lightfoot was the name on everyone’s lips and on the voice on everyone’s radio. An evocative portrayal of the break up of his first marriage, it combines heartfelt lyrics with one of the most powerful vocal performances of his career. The guitar playing, meanwhile, needs to be listened to to be believed. It topped the charts in Canada, peaked at No.1 on the US Easy Listening chart, No. 5 on the Billboard Hot 100, No. 30 in the UK, and entered the Top 20 in numerous other countries. Gordon had arrived.

2. The Wreck of the Edmund Fitzgerald


Named as one of the best Gordon Lightfoot songs of all time by, The Wreck of the Edmund Fitzgerald tells the real-life story of the Edmund Fitzgerald, an ore carrier that sank in Lake Superior in 1975 and took 29 nine members of the crew with it. Wistful but not maudlin, beautifully arranged, and blessed with some truly stupendous lyrics, it remains one of his most poignant and popular songs. Released just one year after the disaster, it sailed to No. 1 in his native Canada and No. 2 on the US Billboard Hot 100.

1. Sundown


Rounding off our list of the 10 best Gordon Lightfoot songs of all time is Sundown, a deeply personal, highly evocative song inspired by Lightfoot’s volatile relationship with Cathy Smith, who later served 15 months in prison due to her role in the death of comedian John Belushi. As dark as the relationship itself, Sundown has been described by Lightfoot as a “back-alley kind of tune. It’s based on infidelity – I’ve seen both sides of that.” Released in March 1974, it became Lightfoot’s biggest ever hit, reaching No. 1 on both the U.S. Billboard Hot 100 and easy listening charts.

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