Rosenberg studied Irish literature at New York University, and began working as an apprentice film editor while in graduate school.[citation needed]
After advancing to film editor, he began directing with episodes of the television series Decoy (1957–1959), starring Beverly Garland as an undercover police woman. It was the first police series on American television built around a female protagonist. Over the next two years, Rosenberg directed 15 episodes of the police-detective series Naked City (1958–1963), which like Decoy was shot in New York City. Meanwhile, Rosenberg was then hired to direct his first film, Murder, Inc. (1960), starring Peter Falk, but a strike by both the Screen Actors Guild and the Writers Guild resulted in his leaving the film and being replaced by its producer, Burt Balaban. Rosenberg returned to television, directing 15 episodes of The Untouchables, eight of the anthology series Bob Hope Presents the Chrysler Theatre, five of Alfred Hitchcock Presents, and three of The Twilight Zone, along with episodes of Adventures in Paradise, The Barbara Stanwyck Show, Ben Casey, Rawhide with Clint Eastwood, and Falk's The Trials of O'Brien. He won a 1963 Emmy Award for directing "The Madman", one of his 19 episodes of the courtroom drama The Defenders.
Following the U.S.-German co-production Question 7 (1961), filmed in West Berlin, Rosenberg shot the 1965 TV movie Memorandum for a Spy and the 1966 telefilm Fame Is the Name of the Game, then made his major-studio debut with the Paul Newman hit Cool Hand Luke (1967). Rosenberg had come across Donn Pearce's chain gang novel and developed the film with actor Jack Lemmon's production company Jalem. Years later, Rosenberg replaced Bob Rafelson on the prison movie Brubaker (1980).

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