Among the topics discussed in this chapter are Milestone’s early experience as a film editor in Hollywood, his friendship with other Russian emigres, his independent disposition and propensity for lawsuits, and his relationships with future mogul Darryl Zanuck and wealthy producer Howard Hughes. The first feature Milestone directed, Seven Sinners, is analyzed, as well as his subsequent silent films The Caveman, The New Klondike, The Garden of Eden, The Racket and Two Arabian Knights, starring Mary Astor and Louis Wolheim, his first collaboration with Hughes. This “buddy comedy” earned him his first Oscar in 1929 for best comedy direction, and established Milestone as one of the most promising directors in Hollywood.