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Robert Montgomery was born Henry Montgomery Jr., the elder son of New York businessman Henry Montgomery and his wife, Mary Weed (Barney), a native of Brooklyn, Kings County, New York. Montgomery had a younger brother, Donald. He was not related to Belinda Montgomery.

As a child, he enjoyed a privileged life. His father, Henry Montgomery, was the president of the New York Rubber Co. When Henry Montgomery died and owing to the Depression, the family fortune was gone. Henry Jr. and his younger brother, Donald, worked at a number of jobs. He later went to New York to be a writer, and on the advice of a friend, tried acting. He worked with George Cukor on the stage and his first film, at MGM, was So This Is College (1929), changing his forename.

When Norma Shearer picked him to be her leading man in Private Lives (1931), he was set. He ran the gamut of different characters over the years. He served as President of the Screen Actors Guild from 1935-38 and 1946-47.. His stay with MGM lasted 16 years, and was only interrupted by WWII when he joined the navy. He saw action in both Europe and the Pacific.

He returned to MGM in 1945 and co-starred with John Wayne in the John Ford-directed They Were Expendable (1945) and then made his directorial debut with Lady in the Lake (1946) (although he had directed a few scenes, uncredited, in They Were Expendable (1945) when John Ford took ill). He left MGM to become an independent director, preferring work behind the camera instead of in front.

A staunch Republican, he was a friendly witness before the House Un-American Activities in 1947 during the McCarthy era and then spent most of his time on television and stage. His popular show, Robert Montgomery Presents (1950), was where his daughter, Elizabeth Montgomery (who later gained lasting fame as beautiful witch Samantha Stevens on Bewitched (1964)), got her first acting job.

Robert Montgomery died of cancer on September 27, 1981, aged 77, at Columbia-Presbyterian Hospital in Manhattan, New York City. His body was cremated and the ashes were given to the family.

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