“Odd Balls” is a 1966 film made at Massey College, featuring Robertson Davies, the first master of the college.
The college was built in 1962, opened in 1963, and was initially all-male.
Some Massey history
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The college itself (not counting the attire of the people in it) and the subway look basically the same as they do now. Other things, like the streetcars, very different.