No single artist is more closely connected to Massey Hall than Gordon Lightfoot. Beginning in 1951 and ’52, as a pre-teen with his first place wins in two Kiwanis Festival singing competitions, Lightfoot has made over 165 appearances (and counting) on its hallowed stage. The Orillia native returned in ’55 with his Teen Timers quartet to take second prize in a barbershop singing contest. Lightfoot’s first concert as a featured singer-songwriter came in March 1967, which one critic described as a “country-and-Lightfoot parade of Canadiana.” Two years later, Canada’s folk star recorded his first live album there, Sunday Concert (his second was 2012’s All Live, drawn from material recorded at Ma...
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