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Portrayed Abraham Lincoln in both Abe Lincoln in Illinois (1940) and How the West Was Won (1962).
Massey`s divorce from his ex-wife Adrienne Allen was the inspiration for the 1949 film Adam`s Rib (1949). Each was represented by one half of a famous husband-and-wife team of divorce lawyers, Dorothy Whitney and her husband William Dwight Whitney. After the trial was over, the Whitneys divorced. The ex-Mrs. Whitney married Massey, and the ex-Mrs. Massey married the ex-Mrs. Whitney`s ex-husband.