Bob Dylan, not one to give compliments lightly, was one of Gordon Lightfoot’s biggest fans. 

"I can’t think of any Gordon Lightfoot song I don’t like," he once said. "Every time I hear a song of his, it’s like I wish it would last forever."

Canadian songwriter Gordon Lightfoot possessed a rare talent to craft the right turn of phrase and pen timeless songs. In a career spanning more than six decades, Lightfoot wrote lingering melodies with carefully chosen words that spoke to generation after generation. He could capture the zeitgeist just as easily as he could write a lasting love song or universal story. He loved to paint pictures of his native land in his compositions. 

On Monday, the legendary songwriter passed away at 84 years old. He leaves behind a catalog of more than 500 songs and 20 studio albums. 

"Gordon Lightfoot captured our country’s spirit in his music — and in doing so, he helped shape Canada’s soundscape. May his music continue to inspire future generations, and may his legacy live on forever," Canada’s Prime Minister Justin Trudeau tweeted.

Lightfoot's fans include fellow prolific songwriter Neil Young, who called him "a Canadian legend." On his website, Young described Lightfoot as "a songwriter without parallel" whose "melodies and words were an inspiration to all writers who listened to his music, as they will continue to be through the ages. There is a unique and wonderful feeling to Gordon's music." 

Susan Stewart, Managing Director of the Recording Academy's Songwriters & Composers Wing, described the four-time GRAMMY nominee as "one of the best songwriters in the world.

"I once had the pleasure of producing a show where he performed. If at first he came off as a bit shy, he emerged as extremely kind and intentional. He told us that he thought of himself as an entertainer, but after being in Nashville, he was proud to be reminded that he was a songwriter," she says. "Gordon’s songs were so vulnerable and honest, and he could weave stories in his lyrics that fired the imagination. Truly one of a kind." 

Born in 1938 in Orillia, Ontario (birthplace of the Mariposa Folk Festival) Lightfoot’s career began in the 1960s coffeehouse folk club circuit. As singer/songwriter, Lightfoot first honed his sound and workshopped his songs in Toronto’s Yorkville neighborhood, later working in New York City’s Greenwich Village. His debut album, Lightfoot!, arrived in 1966.  

The following list easily could be five times as long, but here are five essential Gordon Lightfoot songs that showcase his gifts.

"Early Morning Rain" (1966)

Written in 1964, but not released until 1966 on the album of the same name, "Early Morning Rain" is one of Lightfoot’s most poetic and poignant songs. With lines like "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," the song evokes a feeling of loneliness and homesickness. 

It is one songwriters continually return to as a masterclass in what makes a great song. Judy Collins, Ian & Sylvia and Peter, Paul & Mary all covered this classic. Bob Dylan took his turn at this song in 1970; Lightfoot admitted this was a huge boost to his career as it validated him to a whole new audience that looked to Dylan as the bar when it came to songwriters.      

"Canadian Railroad Trilogy" (1967)

Canada’s national public broadcaster (The CBC) originally commissioned Lightfoot to write this song to mark the country’s centennial celebrations in 1967. It appeared on The Way I Feel, Lightfoot's second studio album. 

Written in just three days, the composition tells the story of the laborers who built Canada’s national railroad, which connected the country from coast to coast. The tempo mimics a train rolling down the tracks. John Mellencamp and George Hamilton IV, among many others, have covered this storied song. 

"If You Could Read My Mind" (1969)

Recorded in Los Angeles for the album Sit Down Young Stranger — his first record for Warner’s Reprise label — this ballad earned the Canadian folk singer his second GRAMMY nomination.

The wistful song was the artist’s first No.1 hit in the U.S., helped him achieve his first gold record, and was inducted into the Canadian Songwriters Hall of Fame in 2003. 

A rumination on his divorce, "If You Could Read My Mind" describes feelings that resonate with anyone who has ever experienced heartache with a pensive melody to match. One of Lightfoot’s most covered songs — Glen Campbell and Olivia Newton-John have offered versions, in addition to unique takes from jazzman Herb Albert and Stars on 54, who turned the track into a disco and pop hit in the late '90s.

"Sundown" (1974)

https://youtu.be/ywUFkWiHznw

Released in 1974 as a single from the album of the same name, "Sundown" is another of Lightfoot’s songs about a complicated relationship. With its dark lyrics and brooding and bluesy melody, this hit chronicles his tumultuous affair with Cathy Smith, who later was charged in the accidental death of actor John Belushi. 

The song reached No. 1 on both the Canadian and U.S. Billboard Hot 100. In 2023, Depeche Mode performed a unique cover of this timeless classic with the BBC Concert orchestra. 

"The Wreck of the Edmund Fitzgerald" (1976)

Released in June 1976 on Summertime Dream, the song peaked at No. 2 on the Billboard charts. It was nominated for a pair of GRAMMY Awards — Song Of The Year and Best Pop Vocal Performance. 

"The Wreck of the Edmund Fitzgerald" showcases the artist’s ability to share a moment in history in song. It’s no wonder it is one of Lightfoot’s most beloved and enduring songs. The song tells the mariner’s tale of the Great Lakes iron ore freighter (the S.S. Edmound Fitzgerald) that mysteriously sank in November 1975. All 29 of the crew perished in the lake called "Gitche Gumee." Verse by verse, strum by strum, Lightfoot takes the listener on this journey in song to share this tragic moment. 

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