Early Life
Massey was born in Toronto, Ontario, the son of Anna (née Vincent), who was American-born, and Chester Daniel Massey, the wealthy owner of the Massey-Ferguson Tractor Company. His branch of the Massey family immigrated to Canada from England . He attended secondary school briefly at Upper Canada College, before transferring to Appleby College in Oakville, Ontario, and taking several courses at University of Toronto, where he was an active member of the Kappa Alpha Society. He later graduated from Balliol College, Oxford.
At the outbreak of World War I, Massey joined the Canadian Army, serving with the artillery on the Western Front. He returned to Canada suffering shell-shock and was engaged as an Army instructor for American officers at Yale. In 1918, he was sent to serve in Siberia, where he made his first stage appearance, entertaining American troops on occupation duty. Severely wounded in action in France, he was sent home, where he eventually worked in the family business, selling farm implements.
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