As one of several sons of the owner of Toronto's Massey/Harris Agricultural Implement Company, Raymond Massey was expected to distinguish himself in business or politics or both (indeed, one of Raymond's brothers, Vincent Massey, later became Governor General of Canada). But after graduating form Oxford University, Massey defied his family's wishes and became an actor. He made his first stage appearance in a British production of Eugene O'Neill's In the Zone in 1922. By 1930, Massey was firmly established as one of the finest classical actors on the British stage; that same year he came to Broadway to play the title role in Hamlet.
In 1931, Massey starred in his first talking picture, The Speckled Band, portraying Sherlock Holmes. One year later, he was co-starred with Charles Laughton, Melvyn Douglas, Gloria Stuart and Ernst Thesiger in his first Hollywood film, the classic The Old Dark House (1932). Returning to England, Massey continued dividing his time between stage and screen, offering excellent performances in such major motion-picture efforts as The Scarlet Pimpernal (1935) and Things to Come (1936). In 1938, he was cast in his most famous role: Abraham Lincoln, in Robert E. Sherwood's Pulitzer Prize-winning Broadway production Abe Lincoln in Illinois. Massey repeated his Lincoln characterization in the 1940 film version of the Sherwood play, and 22 years later played a cameo as Honest Abe in How the West Was Won (1962).