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Gordon Lightfoot has always been fascinated by big mechanical things like trains and boats and planes, and man’s relationship to them. Three of his most famous songs, “Early Morning Rain,” “Canadian Railroad Trilogy” and “The Wreck of the Edmund Fitzgerald,” deal in the romance and tragedy of human interaction with the machinery of those forms of transportation. Personal and poetic, “Early Morning Rain” expressed a palpable longing while expertly contrasting the rural past and urban present in one brilliant line about freight trains and jet planes. Lightfoot placed himself directly in the story, summoning his own experience of travel and homesickness for inspiration. His memories of big 707s...

Gordon Lightfoot has had some remarkable artists record his songs. Elvis Presley, Judy Collins and Bob Dylan have all lent their distinctive voices to “Early Morning Rain” and Barbara Streisand, Johnny Cash and Diana Krall have each interpreted “If You Could Read My Mind.” “Sundown,” meanwhile, has been given wildly varied punk and hip-hop treatments by acts such as Elwood and Clawhammer. But the Lightfoot song that has attracted by far the coolest attention has been “I’m Not Sayin.’” For that, credit goes to the German-born chanteuse Nico, later of Velvet Underground fame. The influence of her 1965 version, with production and guitar accompaniment by the Rolling Stones’ Brian Jones and futu...

One of Gordon Lightfoot’s best-known songs was born out of a dying marriage. With its visions of wishing-well ghosts, movie queens and paperback novels, “If You Could Read My Mind” contains some of Lightfoot’s most vivid imagery. Emotionally, the lyrics stand out for their startling honesty. The words had poured out of him one afternoon in 1969, while sitting alone in an empty house. Baring his soul like never before, he’d written lines like “I don’t know where we went wrong, but the feeling’s gone and I just can’t get it back.” There was little doubt it was about his broken marriage. The words “heroes often fail” suggest he blamed himself for its demise, but the phrase “chains upon my feet”...

Gordon Lightfoot became a star at home during Canada’s centennial year. South of the border, he was still mostly known as the composer of hits for others, including Marty Robbins and Peter, Paul and Mary. All that changed in 1968. Why it didn’t happen earlier had a lot to do with the delayed release of the Canadian artist’s debut album, Lightfoot! Although recorded late in 1964, it didn’t appear until over a year later, by which time the folk boom had largely gone bust, thanks to the twin forces of the Beatles and an electrified Bob Dylan. Lightfoot was working hard at playing catch up, releasing The Way I Feel and touring relentlessly throughout ’67. By early the following year, the tide wa...

It is the most patriotic of all his songs, a three-part epic that recounts the construction of a nation-spanning railway, describes the stark beauty of a country’s landscape and tells of the human toil it took to build the “iron road runnin’ from the sea to the sea.” And yet Gordon Lightfoot’s “Canadian Railroad Trilogy” managed to resonate with listeners on both sides of the 49th parallel when it was released 50 years ago. Appearing on Lightfoot’s 1967 album The Way I Feel, the “Trilogy” was instantly embraced by Canadians already deep into celebrating their country’s 100th anniversary. But Americans somehow connected with the song as well. When Lightfoot launched into the robust ballad the...