His 1967 film Bonnie and Clyde is credited with initiating the New Hollywood movement, by infusing the biographical crime drama with a counterculture sensibility.

[1] 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.

In the 1990s, he returned to stage and television direction and production, including an executive producer role for the police procedural series Law & Order.

[12] After making a name for himself as a director of quality television dramas, Penn made his feature debut with The Left Handed Gun (1958) for Warner Brothers.

A retelling of the Billy the Kid legend, it was distinguished by Paul Newman's portrayal of the outlaw as a psychologically troubled youth (the role was originally intended for James Dean).

[13] Penn's second film was The Miracle Worker (1962), the story of Anne Sullivan's struggle to teach the blind and deaf Helen Keller how to communicate.

Heavily influenced by the French New Wave, it was the dreamlike story of a standup comedian (played by Warren Beatty) on the run from sinister, ambiguous forces.

"[16] Penn's next film was The Chase (1966) a thriller following events in a small corrupt Southern town on the day an escaped convict, played by Robert Redford, returns.

Indeed, there was a strong resurgence in the "love on the run" subgenre in the wake of Bonnie and Clyde, peaking with Badlands (1973; in which Penn received acknowledgement in the credits).

[17] At the time he had completed Bonnie and Clyde, Penn was residing in Stockbridge, Massachusetts, when he heard a story of a large-scale littering incident that had happened in the town two years prior.

[4] In 1973 Penn provided a segment for a promotional film for the Olympics titled Visions of Eight along with several other major directors such as John Schlesinger and Miloš Forman.

[22] Subsequently, Penn returned to work in television, including as an executive producer for the crime series Law & Order.