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Born in Ukraine, Milestone came to America as a tough, resourceful Russian-speaking teenager and learned about film by editing footage from the front as a member of the Signal Corps of the US Army during World War I. During the course of his film career, which spanned more than 40 years, Milestone developed intense personal and professional relationships with such major Hollywood figures as Howard Hughes, Kirk Douglas, Marlene Dietrich, and Marlon Brando. Addressed are Milestone’s successes―he garnered 28 Academy Award nominations―as well as his challenges. Using newly available archival material, this work also examines Milestone’s experience during the Hollywood Blacklist period, when he was one of the first prominent Hollywood figures to fall under suspicion for his alleged Communist sympathies.