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Lightfoot was born in Orillia, Ontario, to Gordon Lightfoot, Sr., who managed a local dry cleaning firm, and Jessie Vick Trill Lightfoot. He had one sister, Beverley (1935-2017). His mother recognized Lightfoot’s musical talent early on and schooled him into a successful child performer. His first public performance was “Too Ra Loo Ra Loo Ral” (an Irish lullaby) in fourth grade, which was broadcast over his school’s public address system on a parents’ day event. As a youth, he sang, under the direction of choirmaster Ray Williams, in the choir of Orillia’s St. Paul’s United Church. According to Lightfoot, Williams taught him how to sing with emotion and how to have confidence in his voice. Lightfoot was a boy soprano; he appeared periodically on local Orillia radio, performed in local operettas and oratorios, and gained exposure through various Kiwanis music festivals. At the age of twelve, after winning a competition for boys whose voices had not yet changed, he made his first appearance at Massey Hall in Toronto. As a teenager, Lightfoot learned piano and taught himself to play drums and percussion. He held concerts in Muskoka, a resort area north of Orillia, singing “for a couple of beers.”
Lightfoot performed extensively throughout high school, Orillia District Collegiate & Vocational Institute (ODCVI), and taught himself to play folk guitar. A formative influence on his music at this time was 19th-century master American songwriter Stephen Foster. He was also an accomplished high school track-and-field competitor and set school records for shot put and pole vault, as well as being the starting nose tackle on his school’s Georgian Bay championship winning football team. His athletic and scholarly aptitude earned him entrance bursaries at McGill University’s Schulich School of Music and the University of Toronto, Faculty of Music.
Lightfoot moved to California in 1958 to study jazz composition and orchestration for two years at Hollywood’s Westlake College of Music, which had many Canadian students. To support himself, he sang on demonstration records and wrote, arranged, and produced commercial jingles. Among his influences were the folk music of Pete Seeger, Bob Gibson, Ian and Sylvia Tyson, and The Weavers. He rented lodging in Los Angeles for a period, but missed Toronto and returned there in 1960, living in Canada since, though he has done much work in the United States, under an H-1B visa.
After his return to Canada, Lightfoot performed with The Singin’ Swingin’ Eight, a group featured on CBC TV’s Country Hoedown, and with the Gino Silvi Singers. He soon became known at Toronto folk music oriented coffee houses. In 1962, Lightfoot released two singles, both recorded at RCA in Nashville and produced by Chet Atkins, that were local hits in Toronto and received some airplay elsewhere in Canada. “(Remember Me) I’m the One” reached No. 3 on CHUM radio in Toronto in July 1962 and was a top 20 hit on Montreal’s CKGM, then a very influential Canadian Top 40 radio station. The follow-up single was “Negotiations”/”It’s Too Late, He Wins”; it reached No. 27 on CHUM in December. He sang with Terry Whelan in a duo called the “Two-Tones”. They recorded a live album that was released in 1962 called Two-Tones at the Village Corner (1962, Chateau CLP-1012).
In 1963, Lightfoot travelled in Europe and in the United Kingdom, and for one year he hosted BBC TV’s Country and Western Show, returning to Canada in 1964. He appeared at the Mariposa Folk Festival and began to develop a reputation as a songwriter. Ian and Sylvia Tyson recorded “Early Mornin’ Rain” and “For Lovin’ Me”; a year later both songs were recorded by Peter, Paul and Mary; other performers who recorded one or both of these songs included Elvis Presley, Chad & Jeremy, George Hamilton IV, The Clancy Brothers, and the Johnny Mann Singers. Established recording artists such as Marty Robbins (“Ribbon of Darkness”), Leroy Van Dyke (“I’m Not Saying”), Judy Collins (“Early Morning Rain”), Richie Havens and Spyder Turner (“I Can’t Make It Anymore”), and The Kingston Trio (“Early Morning Rain”) all achieved chart success with Gordon Lightfoot’s material.