All 19 Leo Penn Movies (in Order)

Paige Gonzalez
8 min readApr 5, 2024

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Dive into the world of cinema with our roundup of the top Leo Penn movies. From heart-warming dramas to thrilling action films, we’ve compiled a list of must-watch films that showcase both Leo Penn’s acting talent and his versatility on the silver screen. Get ready to embark on a cinematic journey and discover the magic of Leo Penn’s movies.

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1. The Best Years of Our Lives (1946)

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The Best Years of Our Lives” is a poignant and thought-provoking drama set in the wake of World War II. The film follows the lives of three war veterans as they return to the American Midwest and attempt to readjust to civilian life.

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2. Not Wanted (1949)

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Not Wanted” is a gripping drama released in 1949, directed by Elmer Clifton and Ida Lupino, and written by Paul Jarrico, Ida Lupino, and Malvin Wald. The film explores the complexities of unplanned pregnancy and sexual issues, leaving a lasting impact on its viewers.

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3. The Undercover Man (1949)

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The Undercover Man” (1949) is a captivating crime drama that follows the journey of Treasury Department agent Frank Warren in pursuit of a cunning mob leader. Warren uncovers hidden secrets as he unravels a case of unpaid taxes on the mob’s illicit gains. Directed by Joseph H.

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4. The Veil (1958)

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The Veil” is a chilling anthology of horror stories, set to captivate you with its spine-tingling tales. This 3-hour, 20-minute film, released in 1958, is hosted by no other than the legendary Boris Karloff, who adds an extra layer of terror to the mix with his unforgettable presence.

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5. The Story on Page One (1959)

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The Story on Page One” is a gripping 1959 drama, where the tension is palpable as an illicit couple finds themselves on trial for the murder of the husband of the cheating female partner. This courtroom drama, directed by Clifford Odets, masterfully weaves together elements of intrigue and suspense. The film stars Rita Hayworth, Anthony Franciosa, and Gig Young, who bring their A-game to the screen as they dive headfirst into a web of deceit, violence, and retribution.

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6. Birdman of Alcatraz (1962)

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Experience the captivating true story of “Birdman of Alcatraz, “ a 1962 drama film that explores the journey of a convicted murderer turned renowned bird expert. Based on the life of Robert Stroud, John Frankenheimer’s riveting directorial work stars Burt Lancaster, Karl Malden, and Thelma Ritter as the lead characters.

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7. A Man Called Adam (1966)

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A Man Called Adam is a 1966 drama film that explores the challenges and pressures faced by a famous jazz trumpeter. Starring Sammy Davis Jr. , Ossie Davis, and Louis Armstrong, the movie centers around the life of a talented musician who struggles to adapt to the complexities of everyday life. With an impressive jazz score and an ensemble cast that includes legendary jazz artists, A Man Called Adam delves into themes of prejudice and the consequences of talent when left unchecked.

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8. Quarantined (1970)

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In the gripping 1970 drama “Quarantined, “ a family of doctors faces a deadly battle against a cholera epidemic, which takes a dramatic turn when a famous movie star refuses treatment. In a small town’s medical clinic, tense situations unfold as the doctors strive to save lives while grappling with the celebrity’s uncooperative stance.

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9. Sixth and Main (1977)

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Sixth and Main is a deeply moving drama film released in 1977, and it showcases the struggles and realities of homelessness in Los Angeles. The story revolves around Monica Cord, a determined journalist who sets out to pen a book about the lives of these unfortunate individuals. Among those she observes is an enigmatic man known only as John Doe, setting the stage for a thought-provoking study of human resilience.

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10. The Country Western Murders (1979)

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Get ready for a thrilling ride of crime and country in ‘The Country Western Murders’ (1979). Originally titled ‘Murder in Music City’, this 1h 35min drama and crime film is set in the world of country western music. A songwriter, looking for a way to save on taxes, purchases a detective agency, unknowingly stumbling upon a real case of murder.

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11. Hellinger’s Law (1981)

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Hellinger’s Law, released in 1981, is a crime drama film directed by Leo Penn and starring Telly Savalas, Morgan Stevens, and Ja’net DuBois. The movie revolves around a flamboyant criminal lawyer, Nick Hellinger, who takes on an unusual case.

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12. The Wild Life (1984)

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The Wild Life, released in 1984, is an entertaining comedy-drama film that takes a lighthearted look at the lives of high-school wrestlers. Directed by Art Linson and written by Cameron Crowe, the movie follows two friends who attend a wild party at a swinging-singles apartment complex.

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13. North Beach and Rawhide (1985)

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North Beach and Rawhide, a 1985 drama, is an engaging story revolving around Rawhide MacGregor, a charismatic ex-convict. With his strong-willed nature, he leads a team devoted to transforming troubled urban delinquents into responsible individuals. Set on an expansive cattle ranch used as a correctional facility, the movie captures a unique blend of heart-pumping rodeo action and profound character development.

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14. The Return of Mickey Spillane’s Mike Hammer (1986)

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In the 1986 action-packed thriller “The Return of Mickey Spillane’s Mike Hammer, “ hardboiled detective Mike Hammer, a veteran of the Vietnam War, is back on the case after being hired to protect a young girl. The film begins with a kidnapping attempt on the daughter of a well-known actress, followed by the mysterious death of the kidnapper. Hammer is tasked with solving the crime and keeping the young girl safe.

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15. Judgment in Berlin (1988)

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In 1988, the thrilling drama “Judgment in Berlin” unfolded, directed by Leo Penn and starring Martin Sheen (Karol Ryszard “Rysh” Wozniak). The film is set in West Germany when an American judge (Sheen) is called upon to make a significant decision — was the hijacking of an East German plane into West Berlin justified?

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16. Columbo Goes to the Guillotine (1989)

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In “Columbo Goes to the Guillotine, “ a chilling crime unfolds when a conceited psychic, who seeks to expose a magician as a fraud, mercilessly beheads his former mentor while the magician rehearses his infamous guillotine trick. Veteran detective Lieutenant Columbo is called upon to decipher the enigma surrounding the murder and unveil the shocking truths behind the magician’s untimely demise. Directed by Leo Penn and written by Richard Levinson, William Link, and William Read Woodfield, this thrilling mystery stars Peter Falk, Anthony Andrews, and Karen Austin.

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17. Nasty Boys, Part 2: Lone Justice (1993)

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In “Nasty Boys, Part 2: Lone Justice” (1993), the gripping crime drama is a relentless pursuit of justice. After his son’s tragic death in a drug-related incident, a determined father vows to avenge two Las Vegas police officers. As the stakes get higher, the action-packed film takes you on a harrowing journey of vengeance and redemption.

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18. The Crossing Guard (1995)

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The Crossing Guard” is a gripping drama-thriller from 1995, directed and written by Sean Penn, based on the original screenplay. The movie stars Jack Nicholson, David Morse, and Anjelica Huston. Set against a backdrop of loss, grief, and unrelenting revenge, it tells the tale of Freddy Gale, a seedy jeweller bent on seeking justice after a hit-and-run accident claims the life of his little girl.

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19. Cement (2000)

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Cement” is a gripping crime drama set in L. A. that explores the complexities of human relationships, trust, and betrayal. Directed by Adrian Pasdar and written by Justin Monjo, the film delves into the twisted world of partners, brothers, and spouses, leaving viewers on the edge of their seats.

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