Considered one of the most renowned voices to emerge from Toronto’s Yorkville folk club scene in the 1960s, Lightfoot went on to record 20 studio albums and pen hundreds of songs, including “Carefree Highway” and “Sundown.”
Once called a “rare talent” by Bob Dylan, dozens of artists have covered his work, including Elvis Presley, Barbra Streisand, Harry Belafonte, Johnny Cash, Anne Murray, Jane’s Addiction and Sarah McLachlan.
Most of his songs are deeply autobiographical with lyrics that probe his own experiences in a frank manner and explore issues surrounding the Canadian national identity.
His 1975 song “The Wreck of the Edmund Fitzgerald” chronicled the demise of a Great Lakes ore freighter, and 1966’s “Canadian Railroad Trilogy” depicted the construction of the railway.
“I simply write the songs about where I am and where I’m from,” he once said. “I take situations and write poems about them.”
Often described as a poetic storyteller, Lightfoot remained keenly aware of his cultural influence. It was a role he took very seriously.
“I just like to stay there and be a part of the totem pole and look after the responsibilities I’ve acquired over the years,” he said in a 2001 interview.
While Lightfoot’s parents recognized his musical talents early on, he didn’t set out to become a renowned balladeer.
He began singing in his church choir and dreamed of becoming a jazz musician. At age 13, the soprano won a talent contest at the Kiwanis Music Festival, held at Toronto’s Massey Hall.
“I remember the thrill of being in front of the crowd,” Lightfoot said in a 2018 interview. “It was a stepping stone for me…”
The appeal of those early days stuck and in high school, his barbershop quartet, The Collegiate Four, won a CBC talent competition. He strummed his first guitar in 1956 and began to dabble in songwriting in the months that followed. Perhaps distracted by his taste for music, he flunked algebra the first time. After taking the class again, he graduated in 1957.
By then, Lightfoot had already penned his first serious composition — “The Hula Hoop Song,” inspired by the popular kids’ toy that was sweeping the culture. Attempts to sell the song went nowhere so at 18, he headed to the U.S. to study music for a year. The trip was funded in part by money saved from a job delivering linens to resorts around his hometown.
Life in Hollywood wasn’t a good fit, however, and it wasn’t long before Lightfoot returned to Canada. He pledged to move to Toronto to pursue his musical ambitions, taking any job available, including a position at a bank before landing a gig as a square dancer on CBC’s “Country Hoedown.”
His first gig was at Fran’s Restaurant, a downtown family-owned diner that warmed to his folk sensibilities. It was there he met fellow musician Ronnie Hawkins.
The singer was living with a few buddies in a condemned building in Yorkville, then a bohemian area where future stars including Neil Young and Joni Mitchell would learn their trade at smoke-filled clubs.
Lightfoot made his popular radio debut with the single ”(Remember Me) I’m the One” in 1962, which led to a number of hit songs and partnerships with other local musicians. When he started playing the Mariposa Folk Festival in his hometown of Orillia, Ontario that same year, Lightfoot forged a relationship that made him the festival’s most loyal returning performer.
By 1964, he was garnering positive word-of-mouth around town and audiences were starting to gather in growing numbers. By the next year, Lightfoot’s song “I’m Not Sayin’” was a hit in Canada, which helped spread his name in the United States.
A couple of covers by other artists didn’t hurt either. Marty Robbins’ 1965 recording of “Ribbon of Darkness” reached No. 1 on U.S. country charts, while Peter, Paul and Mary took Lightfoot’s composition, “For Lovin’ Me,” into the U.S. Top 30. The song, which Dylan once said he wished he’d recorded, has since been covered by hundreds of other musicians.
That summer, Lightfoot performed at the Newport Folk Festival, the same year Dylan rattled audiences when he shed his folkie persona by playing an electric guitar.
As the folk music boom came to an end in the late 1960s, Lightfoot was already making his transition to pop music with ease.
In 1971, he made his first appearance on the Billboard chart with “If You Could Read My Mind.” It reached No. 5 and has since spawned scores of covers.
Lightfoot’s popularity peaked in the mid-1970s when both his single and album, “Sundown,” topped the Billboard charts, his first and only time doing so.
During his career, Lightfoot collected 12 Juno Awards, including one in 1970 when it was called the Gold Leaf.
In 1986, he was inducted into the Canadian Recording Industry Hall of Fame, now the Canadian Music Hall of Fame. He received the Governor General’s award in 1997 and was ushered into the Canadian Country Music Hall Of Fame in 2001.
