Already a prominent director on both TV and Broadway, Penn made the move to feature films with this gritty Western about Billy the Kid, starring Paul Newman as the legendary outlaw.
Prior to making this film, Penn had directed the Tony Award-winning stage version of Helen Keller's story, which also starred Patty Duke as Keller and Anne Bancroft as her teacher Annie Sullivan. Both actresses won Oscars for their respective performances.
The intense drama about an escaped convict returning to his hometown in the South featured an all-star cast as long as the Mississippi River—Marlon Brando, Robert Redford, Jane Fonda and Robert Duvall, to name just a few.
Despite some initial negative reviews, Penn's signature film not only defined a decade, but redefined the way movies would be made from here on out. As Depression-era bank robbers, Warren Beatty and Faye Dunaway tapped into the anti-establishment sentiments among young people and movie audiences.
Based on a song by Arlo Guthrie, who also played himself in the lead role, this scathing satire directly reflected the social and political climate of the time.
Penn returned to the Western genre with a film that is not only remembered for putting Native Americans in a positive light, but for effectively aging the then 33-year-old Dustin Hoffman to 121!
Penn managed to bring two acting powerhouses together for this eccentric Western that finds horse thief Jack Nicholson being hunted down by Marlon Brando.