Actor/director/producer. In his early career, from the late '20s to the early '40s, Montgomery was an amiable light comedian and dramatic actor, appearing in almost 40 sound films before 1935. He starred opposite Norma Shearer in Private Lives (1931), Joan Crawford in The Last of Mrs. Cheyney (1937), Carole Lombard in Hitchcock's comedy Mr. and Mrs. Smith (1941) and was nominated for an Academy Award for Night Must Fall (1937) and Here Comes Mr. Jordan (1941). His career took a more serious turn after his stint in World War II. For his first film after returning, They Were Expendable (1945), Montgomery not only starred but assisted John Ford in the direction. He also starred in and directed the Raymond Chandler detective thriller Lady in the Lake, noted for its unique first-person point of view. His attentions then turned to politics and television. Montgomery gave "friendly" testimony before the House Un-American Activities Committee (HUAC) and by the mid '50s was a consultant to Republican President Eisenhower. As a prestigious television producer, he supervised the '50s dramatic anthology series Eye Witness (1953) and Robert Montgomery Presents (1950-57), which offered his daughter Elizabeth her acting debut and which won him an early Emmy Award in 1952.
- Between 1929 and 1934, he made five films with Norma Shearer.
- In 1935, became first president of the Screen Actors Guild.
- Was a lieutenant commander in the Navy during World War II.
- Got his start directing in 1945 when John Ford became ill during the production of They Were Expendable and he oversaw the shooting of the final scenes.
- Directed and starred in 1946's Lady in the Lake; shot the film in a "first person" perspective in which his character was never seen except in a reflection in a mirror or window.
- Hosted the 1948 Academy Awards.
- In the late '40s, had a number of short stories published in popular magazines.
- Coached presidential candidate Dwight D. Eisenhower for his television and public-speaking appearances.
- When Eisenhower became president in 1952, Montgomery was named television adviser and became the first show-business professional to occupy an office in the White House.
- In 1959, he and James Cagney formed Cagney-Montgomery Productions. Their first film was The Gallant Hours, a 1960 biopic starring Cagney and featuring both Cagney and Montgomery's sons had small roles.
- He, daughter Elizabeth and son Robert Jr. all died of cancer.