The 25 best prison movies of all time

A 1947 film noir about life behind the bars of Westgate Prison, “Brute Force” stars Burt Lancaster, Hume Cronyn, Charles Bickford, Yvonne De Carlo and Ann Blyth. Directed by Jules Dassin and written by Richard Brooks, the gritty melodrama centers on the brutal realities of the American prison system in the 1940s yet is still relevant some 70 years later.

Although the 1962 prison film “Birdman of Alcatraz” is largely fictionalized, the protagonist, Robert Stroud, was actually a real person. As the biopic shows, Stroud (Burt Lancaster, yet again) was a convicted murderer who spent much of his life in solitary confinement at Kansas’ Leavenworth Prison as well as the titular Alcatraz. In addition to becoming a bird owner and expert to pass the time, the once-rebellious Stroud also becomes a trusted inmate during his life sentence, eventually finding a bit of fame after a biography about his life is penned. Karl Malden, Thelma Ritter, Telly Savalas, Neville Brand and Betty Field co-star in this acclaimed drama, which earned four Academy Award nominations.

Steve McQueen leads a star-studded cast that also includes James Garner, Richard Attenborough, Charles Bronson, Donald Pleasence and James Coburn in “The Great Escape,” a World War II prison escape film based on Paul Brickhill’s 1950 non-fiction book of the same name. Although the film was partially fictionalized, the book is mostly a first-hand account of the actual mass escape of numerous British prisoners of war from Germany’s Stalag Luft III POW camp in 1944. Directed by John Sturges, “The Great Escape” earned praise from critics and a nomination at both the Oscars and Golden Globes.

Paul Newman had a long, distinguished film career, but his most iconic film might be the 1967 prison drama “Cool Hand Luke.” Newman portrayed the titular character, Lucas “Luke” Jackson, a respectable and likable inmate who can’t seem to stay off the chain gang and out of prison — but not for a lack of trying. Thanks to Newman’s performance, a snappy script and classic scenes like Luke’s hard boiled egg-eating bet, “Cool Hand Luke” earned heaps of praise, four Oscar nods (including a Best Supporting Actor win for George Kennedy) and holds a perfect 100 percent rating on Rotten Tomatoes.

Written by Dalton Trumbo and starring Steve McQueen and Dustin Hoffman, “Papillon” is the story of two men’s repeated attempts to escape imprisonment in French Guiana. Although expensive to shoot, “Papillon” easily beat the budget, earning more than $53 million at the box office. McQueen received a Golden Globe nomination for his role as Henri "Papillon" Charriere, and the film’s score nabbed an Oscar nod. “Papillon” was remade in 2017 by director Michael Noer.

The 1974 comedy “The Longest Yard” was remade three times, but that’s no knock on the original. Starring Burt Reynolds, the film centers on Paul “Wrecking” Crewe (Reynolds), a former NFL quarterback locked up after stealing a sports car, who puts together a team of inmates to take on the prison guards in a game of football. Co-starring actors Eddie Albert, Ed Lauter and Bernadette Peters — as well as actual NFL players Ray Nitschke, Mike Henry, Jim Nicholson, and Ray Ogden, among others—”The Longest Yard” was generally praised and won the Golden Globe for Best Motion Picture, Musical or Comedy, in addition to three addition nominations at the event and one Oscar nod.

In 1970, American college student Billy Hayes was arrested in Turkey for attempting to smuggle out two kilograms of hashish. Initially sentenced to four years, Hayes was later given a 30-year term, leading to numerous escape attempts from his Turkish prison. Hayes’ story was chronicled in the 1977 book “Midnight Express,” which was adapted to film the following year by Oliver Stone, with Brad Davis portraying Hayes. The movie took some liberties, but nevertheless raked in $35 million against a budget of just $2.3 million and received positive reviews from critics.

Through extensive and elaborate planning, three inmates slipped out of Alcatraz Federal Penitentiary in 1962 and entered the chilly waters of the San Francisco Bay. Their bodies were never recovered, and many people believe Frank Morris, John Anglin, and Clarence Anglin subsequently became the only men to successfully escape from the island prison. In 1979, Clint Eastwood, Fred Ward and Jack Thibeau portrayed the three inmates in the Don Siegel-directed “Escape from Alcatraz,” which was praised for its action as well as its accurate portrayal of prison life. 

A new warden (Robert Redford) shows up at Arkansas’ Wakefield State Prison determined to clean up the corruption and abuse running rampant between its walls. However, the problems prove to run even deeper and darker than the warden could have ever imagined. Inspired by the 1967 Arkansas Prison Scandal, “Brubaker” garnered a Best Original Screenplay nod at the Academy Awards, although it was actually based on the 1969 book “Accomplices to the Crime.”

Gene Wilder and Richard Pryor star in “Stir Crazy” as a pair of Hollywood hopefuls who end up framed for a bank robbery and given 125-year sentences. Of course, the two comedians still get into plenty of trouble behind bars in this 1980 Sidney Poitier-directed comedy that grossed more than $100 million at the domestic box office — more than any other film directed by an African-American at the time.

Before Alan Ruck and Ally Sheedy had their breakout roles in “Ferris Bueller’s Day Off” and “The Breakfast Club,” respectively, they both debuted in “Bad Boys” alongside stars Sean Penn, Reni Santoni, Eric Gurry and Esai Morales. The 1983 coming-of-age drama directed by Rick Rosenthal earned praise from critics, especially for the performance of a 23-year-old Penn, who earned a Next Generation Award from the Los Angeles Film Critics Association.

Based on the 1976 Manuel Puig novel of the same name, “Kiss of the Spider Woman” stars William Hurt, Raul Julia and Sonia Braga and was directed by Brazilian director Héctor Babenco. A tale of revolution, love and betrayal in a Brazilian prison, “Kiss of the Spider Woman” received glowing reviews, and Hurt was awarded a Best Actor Academy Award and a BAFTA for his role as transgender inmate Luis Molina. Additionally, the Brazilian-American drama earned Oscar nods for Best Picture, Director and Adapted Screenplay.

“American Me” isn’t an accurate depiction of the Mexican Mafia’s power grab in the California Prison System in the ‘50s and ‘60s, but it’s still a powerful story of Montoya Santana, a Los Angeles youth who starts a gang and ends up spending most of his life locked up. Edward James Olmos directs and stars in the crime drama, which was screened at Cannes and well-received but couldn’t earn enough to match its $16 million budget.

“In the Name of the Father” tells the true story of the Guildford Four and Maguire Seven, two overlapping groups of people who were falsely charged and imprisoned for the IRA bombings of two Guildford, England pubs in 1974. The film received seven Academy Award nominations, including Best Picture, Best Director (Jim Sheridan), Best Actor (Daniel Day-Lewis), Best Supporting Actor (Pete Postlethwaite) and Best Supporting Actress (Emma Thompson).

Not only is “The Shawshank Redemption” arguably the best prison movie, but it’s also often discussed among the greatest films ever made. Directed by Frank Darabont and starring Tim Robbins and Morgan Freeman, “The Shawshank Redemption” is based on a Stephen King short story that was penned 12 years prior. An imaginative and powerful narrative paired with strong performances by the cast led to near-universal acclaim, nearly $60 million at the box office and seven Oscar nominations, including Best Picture and Best Supporting Actor (Morgan Freeman).

“Dead Man Walking” earned four Academy Award nominations, including a Best Actress win for Susan Sarandon, a Best Actor nod for Sean Penn and Best Director for Tim Robbins. The film about a remorseless death row inmate (Penn) also earned more than $80 million and perfect ratings from numerous critics, including Roger Ebert.

Prison life is in no way the focus of the 1995 sci-fi film “12 Monkeys,” but much of it takes place in an underground correctional facility. After all, James Cole (Bruce Willis) only takes part in the experimental time travel trips because he is incarcerated. Cole also spends some time locked up in an insane asylum alongside Jeffrey Goines, played by Brad Pitt in an Academy Award-nominated supporting role. “12 Monkeys” was adapted into a TV show in 2015, which aired for four seasons and 47 episodes on Syfy.

“Sleepers” is a tough film to watch, as it involves the systematic abuse of four young boys by guards at a youth correctional facility. (Not exactly prison, but we’ll count it.) Brad Pitt, Jason Patric, Billy Crudup and Ron Eldard play the adult versions of the boys, who seek revenge on the guards, with Kevin Bacon, Robert De Niro, Dustin Hoffman and Minnie Driver appearing in supporting roles. “Sleepers” made $165 million at the box office, received generally positive reviews, and John Williams nabbed an Oscar nod for his score.

“Con Air” only briefly takes place in prison (but is primarily set in a prison transport plane, so that counts) and holds a tragically low 55 percent rating on Rotten Tomatoes, but we’re including it here because if someone were to ask you to show them what an action movie is, “Con Air” should be the first one you hand them. Produced by Jerry Bruckheimer and starring Nicolas Cage, John Cusack, John Malkovich, Steve Buscemi and Ving Rhames, “Con Air” actually received two Oscar nods: Best Sound and Best Original Song. That song was LeAnn Rimes’  “How Do I Live,” which also received a Razzie nomination for Worst Original Song. It failed to win either award.

Another difficult film to watch, “American History X” doesn’t primarily take place in prison, but the transformation of Derek (Edward Norton) while incarcerated is a pivotal plot point in the 1998 crime drama. Edward Furlong, Elliott Gould, Stacy Keach, Beverly D’Angelo, Ethan Suplee and Fairuza Balk round out the impressive cast, but Norton received most of the praise for his portrayal of a former white supremacist and earned a Best Actor Academy Award nomination.

Stephen King has a knack for penning stories that take place in prison, as the moving 1999 fantasy film “The Green Mile” centers on the inmates and guards on death row at a Louisiana penitentiary. Tom Hanks, Michael Clarke Duncan, Sam Rockwell, James Cromwell, David Morse, Bonnie Hunt, Harry Dean Stanton, Barry Pepper and Gary Sinise star in the Oscar-nominated film that earned nods for Best Picture, Best Supporting Actor (Duncan), Best Screenplay and Best Sound. Duncan also received recognition at the Golden Globes but failed to win at either award show.

In 1966, boxer Rubin Carter was wrongfully convicted of a triple homicide and his tale was immortalized in the 1975 Bob Dylan song “The Hurricane.” Carter was eventually released in 1985, and 14 years later he was played by Denzel Washington in a film directed by Norman Jewison and based on the boxer’s biopic, “The Sixteenth Round.” Although not completely accurate, the film earned favorable reviews from critics and audiences alike, with Washington earning Best Actor nods at both the Oscars and Golden Globes and a win at the latter.

Steve Buscemi appears only briefly in the San Quentin-set crime drama “Animal Factory,” but he actually had a much larger role in the film. “Animal Factory” was Buscemi’s sophomore directorial effort, and he managed to compile a strong cast of Willem Dafoe, Edward Furlong, Danny Trejo, John Heard, Mickey Rourke and Tom Arnold. The prison escape film managed only a pathetic $43,805 at the box office but received near universal praise from critics. 

Never seen “Bronson”? Not surprising, as it made only $2.3 million at the box office. However, the biopic carries some serious star power with Tom Hardy as the lead and Nicolas Winding Refn (“Pusher,” “Drive”) as director and co-writer. Based on the true story of Britain’s most dangerous criminal, boxer Michael Gordon Peterson (aka Charles Bronson), the film was praised by critics — with Hardy receiving plenty of acclaim, even from Bronson himself.

“I Love You Phillip Morris” is a kooky story about a man named Steven (Jim Carrey) who leaves his wife, kids and normal life behind, moves to Miami, lives a new life as a gay man and makes a living as a con artist. He eventually ends up in jail and falls in love with an inmate named Phillip Morris (Ewan McGregor) and spends the rest of the film trying to get Phillip out of jail — and keep himself out as well. Although “I Love You Phillip Morris” barely made more than its budget, it was nevertheless praised by critics and audiences alike, with Carrey’s performance cited as one of the funnyman’s best roles.