Despite being Canadian, Massey became famous for playing archetypal American historical figures. He played abolitionist/insurrectionist John Brown in two films: "Santa Fe Trail" (1940) and again in the low-budget "Seven Angry Men" (1955). The character of Brown is a wild-eyed lunatic in "Santa Fe Trail", whereas he is a well-intentioned but misguided character in the more sympathetic "Seven Angry Men". Massey scored a great triumph on Broadway in Robert E. Sherwood's Pulitzer Prize-winning play "Abe Lincoln in Illinois" despite reservations about Lincoln's being portrayed by a Canadian. He repeated his role in the 1940 film version, for which he was nominated for the Academy Award for Best Actor. Massey again portrayed Lincoln in "The Day Lincoln Was Shot" on "Ford Star Jubilee" (1956), a silent appearance in "How the West Was Won" (1962), and two TV adaptations of "Abe Lincoln in Illinois" broadcast in 1950 and 1951. He once complained jokingly that he was "the only actor ever typecast as a president." His preparation for the role was so detailed and obsessive that one person commented that Massey would not be satisfied with his Lincoln impersonation until someone assassinated him. On stage in a dramatic reading of Stephen Vincent Benét's "John Brown's Body" (1953), Massey, in addition to narrating along with Tyrone Power and Judith Anderson, took on the roles of both John Brown and Lincoln.