He played piano, drums, and guitar as a teenager, and while still in high school he wrote his first song, a current number about the hula hoop craze with a catchy final line: “I think I’m just a chump and I’m gonna lose.” my job because I hula hula hoopin all the time.”
After studying composition and orchestration at Westlake College of Music in Los Angeles, he returned to Canada. For a time he was a member of the Singing Swinging Eight, a singing and dancing troupe on the TV show Country Hoedown, but soon he became part of the Toronto folk scene, performing in the same cafes and clubs as Ian and Sylvia, Joni Mitchell, Neil Young and Leonard Cohen.
He formed a folk duo, the Two Tones, with Terry Whelan, another “Hoedown” performer. The duo recorded a live album, Two Tones at the Village Corner, in 1962. Touring Europe over the next year, he hosted “The Country and Western Show” on BBC television.
As a songwriter, Mr. Lightfoot had progressed beyond the hula hoop, but not very much. His work “had no identity whatsoever,” he told the authors of the Encyclopedia of Folk, Country and Western Music, published in 1969. Before saying, “I was starting to get a point of view, and that’s when I started to improve.”
In 1965 he performed at the Newport Folk Festival and made his US debut at the Town Hall in New York. “Mr. Lightfoot has a rich, warm voice and a deft guitar technique,” wrote Robert Shelton in the New York Times. “With a little more attention to stage persona, he should become quite popular.”
A year later, after signing with Mr. Dylan and Peter, Paul and Mary’s manager, Albert Grossman, Mr. Lightfoot recorded his first solo album, Lightfoot! Featuring performances of “Early Morning Rain”, “For Lovin’ Me”, “Ribbon of Darkness” and “I’m Not Sayin'”, a hit in Canada in 1963, the album received critical acclaim.