Decided to try acting after staging plays for recreation as a member of the Canadian armed forces fighting World War I on the Siberian front.
His deeply religious father would not let him pursue an acting career unless he vowed not to work on the Sabbath.
Made his Broadway debut in 1930 in Symphony in Two Flats.
The film Adam's Rib was inspired by his divorce from Adrianne Allen. After hiring the married lawyers William and Dorothy Whitney to handle legal proceedings, the Whitneys divorced each other and married Allen and Massey, respectively.
His brother Vincent Massey was a prominent Canadian politician.
Was an ardent supporter of Barry Goldwater's 1964 presidential campaign and not only appeared in a campaign film but toured the country with the candidate.
Died on the same day as his The Prisoner of Zenda co-star David Niven.
Has a cocktail named for him, which contains Canadian rye whiskey, ginger syrup and champagne.
1940, Oscar — Best Performance by an Actor in a Leading Role: Nominee
Chester Daniel Massey — Father
Anna Massey — Daughter
Dorothy Whitney — Husband (deceased)
Anna Vincent Massey — Mother
Charles Vincent Massey — Brother
Daniel Massey — Son
Peggy Fremantle — Ex-wife
Geoffrey Massey — Son
Adrianne Allen — Ex-wife
Dorothy Whitney — Stepdaughter
Attended University of Toronto, Victoria College, Toronto, Ontario, Canada; University of Oxford, Balliol College, Oxford, England