Drawing on the influence of the French New Wave, whose films he discovered as a teenager, Penn took a screenplay about a pair of minor, Depression-era criminals and turned it into a darkly comic story that shocked 1967 audiences with its moments of sexuality and sudden bursts of violence. Older critics were turned off by the film, but younger audiences connected with the film’s rebellious sensibilities. Additionally, Bonnie And Clyde would be marked by film historians as the film that heralded the “Film School Generation,” paving the way for directors like Martin Scorsese, Robert Altman, Terrence Malick and Francis Ford Coppola.
Penn got his start directing during the 1950s in the heyday of live broadcasting. His direction of the Playhouse 90 anthology series telling of the story of Helen Keller, The Miracle Worker, earned him an Emmy nomination in 1957. He would restage the story for Broadway two years later and won a Tony Award. In 1962, he adapted the story again, this time for the silver screen and earned an Academy Award nomination for his efforts.
Penn’s first feature film was the 1958 Paul Newman-starring western The Left-Handed Gun, a low-budget film for which Penn drew on much of his television experience. After being fired from The Train (1964) after a few days filming, Penn’s next film was 1965’s Mickey One. Although it fared poorly at the box-office, it did pair Penn with actor Warren Beatty. When Beatty signed on to star in and produce Bonnie And Clyde, he was insistent that Penn be brought onto the project to direct.
Although he continued to make films, Penn was never able to fully duplicate the success he had with Bonnie And Clyde with the follow-ups Alice’s Restaurant, Little Big Man and Night Moves, but by the mid 1970s, he found that the shift towards blockbuster filmmaking was rendering his style of more intimate and artistic storytelling out of vogue. In between stage work, he did find time to direct a small handful of films including The Missouri Breaks, Target and Penn And Teller Get Killed, his final narrative film.