- He directed 8 different actors in Oscar-nominated performances: Patty Duke, Anne Bancroft, Estelle Parsons, Warren Beatty, Faye Dunaway, Gene Hackman, Michael J. Pollard and Chief Dan George. Duke, Bancroft and Parsons won Oscars for their performances in one of Penn's movies.
- Older brother is renowned photographer Irving Penn.
- Son of a nurse and a watchmaker.
- Was an early contender to direct The Stunt Man (1980) and used elements from that film's source, the Paul Brodeur novel of the same name, in the story of Night Moves (1975).
- Served in the U.S. Army, 1943-46.
- Interviewed in "The Director's Event: Interviews with Five American Filmmakers," by Eric Sherman and Martin Rubin.
- First worked in television studios as a floor manager. Began to write and direct plays for the theatre in 1953. Directed his first Broadway play in 1956 and his first motion picture in 1958. Made only ten films during the first 25 years of his career. His most productive period was 1965-70, when he averaged one movie per year.
- Studied under Michael Chekhov and at the Actor's Studio in Los Angeles.
- He has directed two films that have been selected for the National Film Registry by the Library of Congress as being "culturally, historically or aesthetically" significant: Bonnie and Clyde (1967) and Little Big Man (1970).
- Won Broadway's 1960 Tony Award as Best Director (Dramatic) for "The Miracle Worker." He was also Tony-nominated two other times: in 1958 as Best Director for "Two for the Seesaw." and in 1961 as Best Director (Dramatic) for "All the Way Home."
- The protagonists in his films often tend to be outsiders, either as outlaws (Billy the Kid, Bonnie & Clyde), or cut off from society through circumstance (Little Big Man), disability (Helen Keller) or paranoia (Mickey One).
- [July 14, 2009] Hospitalized with pneumonia in a New York hospital.
- Father of Matthew Penn (born 1959) and Molly Penn (born 1964) with Peggy Maurer.
- Original family name was Michelsohn. His father changed it to Penn upon naturalization in 1916.
- He studied acting so that he could understand the actors side of the business.
- He was in the army during the second world war.
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