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Penn first achieved prominence as a theatre director, winning a Tony Award for Best Direction of a Play for The Miracle Worker. He received similar acclaim and his first Oscar nomination for directing the 1962 film adaptation. His 1967 film Bonnie and Clyde is credited with initiating the New Hollywood movement, by infusing the biographical crime drama with a counterculture sensibility. He achieved similar critical and commercial success directing the comedy Alice's Restaurant (1969) and the revisionist Western Little Big Man (1970), which further reflected that ethos.

Penn’s other notable films included the neo-noir Night Moves (1975) and the revisionist Western The Missouri Breaks (1976). In the 1990s, he returned to stage and television direction and production, including an executive producer role for the police procedural series Law & Order.