Lightfoot was born November 17, 1938 to Jessica Lightfoot and Gordon Meredith Lightfoot in Orillia, Ontario, Canada. As a youth, he sang in the choir of St. Paul's United Church under the direction of choir-master Ray Williams. During this time as a "boy soprano" Lightfoot made several appearances on local radio and local operetta and oratorios as well as Kiwanis music festivals. Lightfoot remarked in 2005 that it was choir master Williams who "taught him how to sing with emotion and how to have confidence in his voice". As a teenager, Lightfoot studied piano and taught himself drums and percussion instruments.
Lightfoot moved to California, where he studied jazz composition and orchestration at Hollywood's Westlake College of Music in 1957-58. He returned to Canada and through 1958 to '61 he was performing with The Swinging Eight a group that appeared on CBC TV's Country Hoedown as well as performing with the Gino Silvi Singers. He also began performing in the coffee houses of the Toronto folk scene, playing guitar and singing folk songs. He sang with Terry Whelan in a duo called the Two Tones and 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 to Europe and became for one year the host of BBC TV's "Country and Western Show". By 1964 he was back in Canada and that year he appeared at the Mariposa Folk Festival.
Lightfoot was gaining some recognition by this time as a songwriter and two of his songs (For Lovin' Me and Early Mornin' Rain) were covered by Ian and Sylvia Tyson. For Lovin' Me was covered again a year later in 1965 by Peter, Paul and Mary, who had a hit with it. That song was again covered by Chad and Jeremy as well as the Johnny Mann Singers. During this time, other artists such as Marty Robbins (Ribbon of Darkness), Leroy Van Dyke (I'm Not Saying), Judy Collins, Richie Havens, The Kingston Trio and Harry Belafonte were racking up hits with Lightfoot's songs. In 1966, his debut album Lightfoot! was released and it brought him recognition as a singer as well as a songwriter. It featured many now-famous songs including For Lovin' Me, Early Mornin' Rain, Steel Rail Blues and Ribbon of Darkness.