He studied with the American Theatre Wing[5] from 1949 to 1951 and began his career as an actor, making his Broadway debut in The Prescott Proposals in 1953.
Three years later, when Hal Prince gained control of the rights to John Van Druten's play I Am a Camera and The Berlin Stories by Christopher Isherwood, he discarded the book for a musical adaptation already written by Sandy Wilson and hired Masteroff to fashion his own.[8] With lyrics and music by Kander and Ebb, Cabaret opened on Broadway in November 1966 and ran for 1,165 regular performances, winning the Tony Award for Best Musical.[9]
Masteroff's next and final Broadway project, 70, Girls, 70 was less successful, closing one month after it opened in April 1971. The music and lyrics were by Kander and Ebb.[10]