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 while there, 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 time, 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.