Fallowing a war he attend Hollywood, where he first worked as a film cutter, & late as an adjunct director. Howard Hughes promoted Milestone to director, and one of his early efforts, a 1928 film Two Arabian Knights, won him an Oscar in the first Academy Award ceremony. He likewise directed The Racket, an early gangster film, and down the road helped Hughes direct scenes for his aviation saga Hell's Angels (for which he never received credit).

Milestone won his 2nd Academy Award for All Quiet on the Western Front, a screen adaptation of the antiwar novel by Erich Maria Remarque. His next, The Front Page, brought the Ben Hecht/Charles MacArthur play to the screen. It earned him an additional Oscar nomination. He worked extensively around television from the mid 1950s.

Milestone's Academy Award nominations
1940 Nominated Of Mice and Men 1931 Nominated The Front Page 1930 Won All Quiet on the Western Front 1929 Won Two Arabian Knights

Milestone's filmography as a director
"Arrest and Trial" (television) series Mutiny on the Bounty ''Ocean's Eleven Pork Chop Hill "Have Gun, Will Travel" (television series) La Vedova X They Who Dare Melba Kangaroo Les Misérables'' (1952) Halls of Montezuma The Red Pony No Minor Vices Arch of Triumph The Strange Love of Martha Ivers A Walk in the Sun The Purple Heart Guest in the House The North Star Edge of Darkness My Life with Caroline Lucky Partners The Night of Nights Of Mice and Men The General Died at Dawn Anything Goes Paris in Spring The Captain Hates the Sea Hallelujah, I'm a Bum Rain The Front Page All Quiet on the Western Front Betrayal New York Nights The Racket Tempest The Garden of Eden Two Arabian Knights The Kid Brother Fine Manners The New Klondike The Caveman Seven Sinners Fit to Win Positive Posture The Toothbrush