Massey portrayed Jonathan Brewster in the film version of "Arsenic and Old Lace". The character had been created by Boris Karloff for the stage version, and a running gag in the play and the film was the character's resemblance to Karloff. Even though the film was released in 1944, it was shot in 1941, at which time Karloff still was contracted to the Broadway play and could not be released for the filming (unlike his costars Josephine Hull, Jean Adair and John Alexander). Massey and Karloff had appeared together earlier in James Whale's suspense film "The Old Dark House" (1932).