Milestone came to the United States in 1917 and served in the First World War.
In 1920 he went to Hollywood and worked as assistant editor and writer with, among others, William A. Seiter. It was the film version of Erich Maria Remarque’s novel. All Quiet on the Western Front, that established Milestone as a leading director, partly because the warning of the film was reinforced by sound, and partly because the battle scenes, contrary to the theme of the movie, were undeniably spectacular.
At this period, Milestone had an inventive, flashy technique that passed for style and a knack of picking or being picked for interesting properties. The Front Page was one of the best early talking comedies, although the talk belonged to Ben Hecht and Charles MacArthur and was to be used rather better by Hawks in His Girl Friday. Rain was a failure; it was a controversial subject, cannily cast: Joan Crawford as Sadie Thompson and Walter Huston as Rev. Atkinson. Hallelujah, I'm a Bum was an eccentric Depression piece, pairing Jolson and Harry Langdon. The Captain Hates the Sea was John Gilbert’s last movie.
Throughout the 1930s, Milestone worked in the theatre as well as the movies and tins added to the idea that he chose his films carefully. In fact, his selection seemed based on variety for its own sake: Anything Goes was an Ethel Merman/Bing Crosby musical; The General Died at Dawn an excellent Gary Cooper adventure set in China; Of Mice and Men an honorable version of Steinbeck, helped by a sensitive performance from Burgess M eredith. Nothing suggested that Milestone was more than a competent director. War showed that he could be a good deal less.
Although his initial reputation rested on a monument against war, his Second World War projects settled for the glamour of battle and the standard group portrait of unambiguous soldiers: The Norih Star, The Purple Heart, A Walk in the Sun, and later. Halls of Montezuma. After the war, the surface excitement flickered out. The Strange Love of Martha Ivers was a rich, neurotic thriller, but Arch of Triumph—again from a Remarque novel—was an overlong commercial failure (it is also the one really disturbing film he made). He had an inexplicable interest in Australian subjects (Kangaroo and Melba) and did a very dull remake of Victor Hugo. Pork Chop Hill was the Korean war, dutifully disenchanted, but still stirring whenever his tracking shots began traversing the battlefield. Ocean’s 11 needed a Gordon Douglas, while Mutiny on the Bounty ran aground on a loathing between Brando and Richard Harris that obscured the original antagonism between Bligh and Fletcher Christian.