As a youth, he sang in the choir of Orillia's St. Paul's United Church under the direction of choirmaster Ray Williams. 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, a venue he would ultimately play over 170 more times throughout his career.
As a youth, he sang in the choir of Orillia's St. Paul's United Church under the direction of choirmaster Ray Williams. 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, a venue he would ultimately play over 170 more times throughout his career.