- Replaced Carol Reed as director of Mutiny on the Bounty (1962) after Reed quit because he could not cope with the massive ego of the film's star, Marlon Brando. Milestone didn't find Brando any easier to work with and in the end let him do as he pleased. When asked by the cameraman why he wasn't watching the filming, Milestone replied, "I hate to see movies in pieces, so you let him do this and when it's all finished and cut, for ten cents I can walk into the theatre and see the whole thing at once. Why should I bother to look at it now?".
- The first person to win two Best Director Oscars: Best Director (Comedy) for Two Arabian Knights (1927) and Best Director for All Quiet on the Western Front (1930). This actually made him the first person to win two Academy Awards (in any category).
- Won the only ever Best Comedy Director Oscar (for Two Arabian Knights (1927)) at the first Academy Awards ceremony in 1929.
- His career was adversely affected during the "Red Scare" era in the late 1940s and early 1950s. To avoid being a target of anti-Communist hysteria whipped up by the House Un-American Activities Committee--which was desperately trying to find "Communist subversion" in Hollywood films--he began making films abroad, in both Britain and Italy, but they were not successful. His last three films were Hollywood productions with large budgets, but he had a bad time on all of them--Gregory Peck re-edited Pork Chop Hill (1959) (which he co-produced); Frank Sinatra and his "Rat Pack" seem to have largely ignored him on the set of Ocean's Eleven (1960), and he had the worst experience of his career trying to direct Marlon Brando on Mutiny on the Bounty (1962) remake. This last was also a hugely expensive box-office failure. Milestone was then scheduled to direct PT 109 (1963), a film about President John F. Kennedy's wartime adventures, but was replaced by a minor TV director, Leslie H. Martinson. After that, he seems to have given up on films, although he directed a few television series episodes, an experience he did not enjoy.
- After winning two Best Director Oscars, he became the first director to be nominated in three different years when he was given a nod for The Front Page (1931).
- Directed five Oscar Best Picture nominees: The Racket (1928), All Quiet on the Western Front (1930), The Front Page (1931), Of Mice and Men (1939) and Mutiny on the Bounty (1962), with "All Quiet on the Western Front" winning Best Picture in 1930.
- A founding member of the Directors Guild.
- Born in Russia, he emigrated to the US in 1917 in order to escape being drafted into the Russian army during World War I, but upon his arrival in the US immediately enlisted in the US Army and was sent to France, where he fought until the war's end.
- Directed two actors to Oscar nominations: Adolphe Menjou (Best Actor, The Front Page (1931)) and Akim Tamiroff (Best Supporting Actor, The General Died at Dawn (1936)).
- A device he used in most of his war films--i.e., All Quiet on the Western Front (1930), Edge of Darkness (1943), A Walk in the Sun (1945) and Pork Chop Hill (1959)--is the dolly shot that moves across infantry attacking toward the camera in echelon and being felled one at a time by machine-gun fire.
- Biography in: John Wakeman, editor. "World Film Directors, Volume One, 1890-1945". Pages 770-778. New York: The H.W. Wilson Company, 1987.
- Cousin of virtuoso violinist Nathan Milstein.
- He and his wife regarded 'Christopher Riordan as family. They often referred to him as "the son we never had".
- He has directed three films that have been selected for the National Film Registry by the Library of Congress as being "culturally, historically or aesthetically" significant: All Quiet on the Western Front (1930), The Front Page (1931) and A Walk in the Sun (1945).
- A Ukrainian immigrant who served in the 1st World War.
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