40 Best Prison Movies You Can’t Escape From

40 Best Prison Movies You Can’t Escape From

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Prison movies are a prominent genre of movies that span several other subgenres. To qualify for this list, a film must be centered on the escape, both tonally and practically, emphasizing the circumstances that necessitate the escape, the process of planning and strategizing the escape (including through teamwork), the actual escape, being pursued or recaptured, and/or a general atmosphere of fear, fascism, paranoia, and injustice.

There are a lot of prison movies available. While some movies use fantasy and science fiction to create beautiful works of escape, prison movies make a concerted effort to depict the drama that exists in our actual world. Anyway, continue reading as I present you the 40 best prison movies you really must watch.

1. Escape From Alcatraz (1979)

40 Best Prison Movies Zou Can’t Escape From (2021 Update)

Alcatraz is one of the world’s most famous prisons. It is located just off the coast of San Francisco and is now a tourist attraction and museum. It was a jail from the 1930s through the 1960s and is brimming with fascinating stories. This film recounts how the three inmates escaped. It was hailed as one of the greatest films of its day and stars the legendary Clint Eastwood.

The actual account of three convicts attempting a daring escape from Alcatraz Island’s famed jail. Although no one had ever escaped before, bank robber Frank Morris (Clint Eastwood) orchestrated this intricately organized, and ultimately successful, escape. This supposedly impregnable federal jail, which held Al Capone and “Birdman” Robert Stroud, was only breached once in twenty-nine years by three convicts who went missing.

2. Brute Force (1947)

A 1947 film noir about life behind the gates of Westgate Prison, the gritty melodrama focuses on the terrible reality of the American prison system in the 1940s and remains pertinent 70 years later.

Warden A. J. Barden is a weak man in Westgate Penitentiary, and the institution is truly run by the arrogant and cruel Captain Munsey, who controls the convicts via brutality, terror, and betrayal. Following Tom Lister’s death, instigated by Captain Munsey, the convicts lose their privileges, and the remainder of the cell R-17 gang, led by Joe Collins, is sent to hard and insalubrious labor in the drain pipe.

Joe employs an effective battle plan in his attempt to escape, attacking the penitentiary’s tower from the outside with his troops and from the inside with the squad led by Gallagher. The plot, however, fails, resulting in carnage.

3. Birdman of Alcatraz (1962)

While the 1962 prison picture “Birdman of Alcatraz” is mostly dramatized, the protagonist, Robert Stroud, was based on a true story. As the movie demonstrates, Stroud (also played by Burt Lancaster) was a convicted killer who spent the majority of his life in solitary confinement at Kansas’ Leavenworth Prison and the eponymous Alcatraz.

As a prisoner in Leavenworth, Robert Stroud has a series of conflicts with guards and fellow inmates. When Stroud murders a guard, he is condemned to death, and it is only through his mother’s emotional intercession that his sentence is commuted to life in solitary confinement.

While he is serving his sentence in boredom and sorrow, he comes upon a defenseless young sparrow in the exercise yard one day. Stroud quickly develops a passion for bird care, which provides him with a new purpose in life but also results in fresh disputes with prison officials.

4. The Shawshank Redemption (1994)

Based on another Stephen King novel, this film is so beloved that some believe it is one of the greatest films of all time (not just prison movies). Andy Dufresne is the protagonist of the narrative after he is convicted of murdering his wife and her boyfriend. When cinema aficionados consider the prison genre, this is frequently the first film that springs to mind.

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Andrew Dufresne, a hotshot financier, is sentenced to Shawshank Prison for the murder of his wife. He maintains optimism over the years and ultimately earns the respect of his fellow convicts, particularly long-term criminal “Red” Redding, a black marketeer, and develops influence within the jail. Andrew eventually accomplishes his goals on his terms.

5. The Great Escape (1963)

40 Best Prison Movies Zou Can’t Escape From (2021 Update)

The Great Escape, a three-hour-long epic based on actual events about a group of Allied(/Antifa) inmates attempting a massive escape from a Nazi POW camp, has it all—and everyone!

A group of allied escape artist-type POWs is all confined to an “escape-proof” camp. Their leader decides to attempt the annihilation of several hundred at once. The first part of the film is a comedy, with the inmates outwitting their jailers to build the escape tunnel. The second part is a great adventure as they escape occupied Europe via aircraft, trains, and boats.

6. Cool Hand Luke (1967)

Paul Newman has a lengthy and brilliant cinematic career, but the 1967 prison drama “Cool Hand Luke” may be his most memorable picture. Newman portrays Lucas “Luke” Jackson, a decent and pleasant convict who can’t manage to keep away from the chain gang and out of jail — but not for a lack of trying.

Lucas Jackson is a natural-born world changer, a man with more guts than intellect, a man who refuses to play by the rules. Luke quickly wins respect and becomes an idol after being sent to a prison camp for a misdemeanor.

He had some fun in jail doing things just for the sake of it, but when his mother dies, the Bosses put him in the box out of fear he might attend the burial. When he escapes, he runs and runs and runs, and the bosses attempt to break him but he would not yield.

7. Escape From New York (1981)

In the future, crime has spiraled out of control, and Manhattan in New York City has been transformed into a maximum security jail. All of the city’s bridges are mined, a huge wall is constructed along the seashore, and a large police force army is stationed there to apprehend or kill any attempted escapees. While en way to a summit meeting between China and the Soviet Union, the President aboard Air Force One is forced to evacuate in an escape pod after a female terrorist seizes control of the jet and crashes it into a downtown skyscraper.

A new prisoner, ex-soldier Snake Plissken, is promised his freedom provided he enters, frees the President, and discovers a recording with vital conference information. Snake accepts, but to secure his cooperation, he is injected with a small yet very explosive microcapsule that will be detonated only if his mission is a success. Snake must venture into a decrepit city teeming with immoral criminals and succeed – for the sake of his own life.

8. Papillon (1973)

“Papillon,” written and directed by Dalton Trumbo and starring Steve McQueen and Dustin Hoffman, is the story of two men’s persistent attempts to evade arrest in French Guiana. Despite its high production costs, “Papillon” comfortably exceeded the budget, grossing more than $53 million at the box office.

Based on the actual story of Henri Charriere, alias Papillon, which translates as ‘butterfly’ in French (the character even sports a large tattoo of a butterfly). Papillon, a minor crook, is wrongfully accused of murder and condemned to life in a French prison colony called ‘Guiane’ (French Guiana, South America). Papillon is desperate to escape, but each effort is met with difficulty, ultimately culminating in his recapture. He continues to attempt escape after being sentenced to solitary prison.

9. Escape Plan (2013)

Ray Breslin is a well-known expert in prison break operations at maximum-security institutions. He co-owns a business with Lester Clark and works with employees and pals Abigail and Hush. Breslin’s escape strategy is based on three fundamental principles: familiarity with the layout, adherence to the routine, and obtaining internal or external backing for the escape. Then he provides his customer with a report outlining the system’s faults. Breslin and his crew are paid five million dollars by CIA agent Jessica Miller to evaluate a state-of-the-art facility.

Breslin accepts the challenge but soon discovers he has been duped. Hobbes, the sadistic jail ward, pays special attention to Breslin, acting on his client’s instructions and using his right arm Drake to break Breslin. However, prisoner Rottmayer develops a relationship with Breslin and assists him in devising a plan to escape and ascertain who betrayed him. Will they be successful in their endeavors?

10. The Experiment (2001)

40 Best Prison Movies Zou Can’t Escape From (2021 Update)

The film is based on the controversial 1971 “Stanford Prison Experiment.” In a research facility, a mock jail is put up, replete with cells, bars, and surveillance cameras. Twenty male volunteers are engaged for two weeks to portray inmates and guards.

The ‘prisoners’ are segregated and required to adhere to seemingly modest regulations, while the ‘guards’ are instructed to maintain order without resorting to physical violence. Everybody has the right to leave at any moment and forfeit the money. At first, both groups’ moods are uneasy and quite assertive. However, quarrels quickly develop, and the wardens resort to more severe punishments to maintain their control.

11. The Longest Yard (1974)

Three times, the 1974 comedy “The Longest Yard” was recreated, but that is no reflection on the original. The film, which stars Burt Reynolds, follows Paul “Wrecking” Crewe (Reynolds), a former NFL quarterback who is imprisoned for stealing a sports vehicle and assembles a team of prisoners to take on the prison guards in a game of football.

Paul Crewe (Reynolds), a former football star, spirals out of control after being discovered shaving points to wager on games. Crewe is sentenced to prison after making some poor choices, and the warden has his eye on him to coach their semi-pro club. Crewe finds himself among the dregs of the prison labor after refusing to comply with the chief guard’s coercive request.

Finally, the warden decides to repurpose him and assigns him the duty of assembling an all-inmate football team for a tune-up game against the guards. Crewe unites his troops and pushes the guards through their paces in an all-out roughed-up guard on the prisoner football game.

12. Midnight Express (1978)

Billy Hayes, an American college student, is apprehended on October 6, 1970, attempting to transport narcotics out of Turkey. Turkish courts decide to punish him severely, condemning him to almost thirty years in jail.

The jail atmosphere is unpleasant in every way, with a nasty prison guard named Hamidou in charge, who takes pleasure in torturing the captives for any reason. Hayes has two avenues for release: through his lawyer’s, family’s, and the American government’s pleas, or by the “Midnight Express.”

13. The Green Mile (1999)

For prison officer Paul Edgecomb, it’s simply another day on the Green Mile. That is until the colossal John Coffey is dispatched there. Unlike the huge behemoth that Coffey appears to be, he is a gentle soul. While keeping an eye on Coffey, Edgecomb discovers that there is more to Coffey than meets the eye.

14. In the Name of the Father (1993)

Based on the actual tale of Gerry Conlon (Daniel Day-Lewis), a Belfast teenager who was wrongfully accused of bombing two pubs outside of London along with family members and friends. A story of a man and his son, who battled for justice to clear his father’s name.

15. Con Air (1997)

40 Best Prison Movies Zou Can’t Escape From (2021 Update)

Few years are lived to the hilt in the manner which Nicolas Cage did in 1997. CON AERIAL AND FACE/OFF Incredible. He portrays “recently paroled ex-con and former United States Ranger Cameron Poe,” who is on his way to a new life of liberty.

Cameron Poe, a highly decorated Army Ranger, returns to Alabama to visit his wife Tricia, only to encounter a few inebriated regulars at the bar where she works. Cameron unintentionally kills one of the drunks and is sentenced to seven years in federal prison for involuntary manslaughter. He now qualifies for parole and may return to his wife and daughter.

Unfortunately for Cameron, he is forced to share a prison jet with some of the country’s most dangerous criminals, who seize control of the aircraft and are now plotting their escape. Cameron must devise a means to thwart them while continuing to play along. Meanwhile, US Marshal Vince Larkin is attempting to assist Cameron in escaping and apprehending the criminals, commanded by Cyrus “The Virus” Grissom.

16. Bronson (2008)

In 1974, a brash 19-year-old called Michael Peterson decided he wanted to make a name for himself and attempted to steal a post office with a handmade sawn-off shotgun and a mind full of fantasies.

Peterson was arrested quickly and was sentenced to seven years in prison. He has already served 34 years in prison, 30 of which have been spent in solitary confinement. During that time, Michael Petersen the kid faded away and his celebrity alters ego, ‘Charles Bronson,’ took center stage. Bronson’s thoughts – a harsh critique on celebrity culture

17. Get the Gringo (2012)

A getaway driver on his way to the arid Mexican border with almost $2 million in loot stashed in the boot of his car ends up in the notorious “El Pueblito” prison. As the only American detainee in the hazardous town of prisoners, the driver quickly earns the moniker “The Gringo” and learns firsthand what it’s like to be a foreigner in a world of crooks.

To survive in this pit where everyone is aware of the huge reward, the Gringo will have to establish an odd alliance with an uncommon ally: a streetwise ten-year-old child who possesses a strange immunity in this insane environment. Now, with a massive target on his back and a limited amount of time remaining, will the Gringo be able to save himself and obtain the money?

18. A Prophet (2009)

Malik El Djebena, an illiterate eighteen-year-old Franco-Algerian, is sentenced to six years in jail for attacking police officers. Alone and without money, Malik finds himself exposed to a corrupt and violent society divided between Corsican and Muslim gangs.

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César Luciani, a powerful Corsican mobster, coerces him into killing the Muslin Reyeb and then supports and protects him within his gang. Malik becomes friends with Ryad, who teaches him to read and write. The two become closest friends. Meanwhile, César employs Malik to assist him outside of jail in his dubious gambling operation. Malik also learns how to distribute narcotics and rises through the ranks of César’s mafia’s hierarchy.

19. Law Abiding Citizen (2009)

The family of Clyde Shelton is brutally killed. The perpetrators are apprehended. However, as a result of the faulty procedure, District Attorney Nick Rice has only circumstantial evidence. As a result, he arranges for one of them to testify against the other. Shelton is not pleased when he learns of this.

Ten years later, the condemned individual is scheduled for death but something goes wrong; his execution is botched and he suffers. They discover that the machine has been tampered with. And the other is discovered dead, brutally murdered. Rice suspects Shelton and arranges for his arrest.

Shelton first agrees to a plea bargain with Rice but later reverses his decision. Shelton does not appear to be finished; he appears to be blaming the entire system and declaring war on it, going after everyone involved in his family’s case. Rice must therefore halt him, but Shelton is far ahead of him.

20. American History X (1998)

40 Best Prison Movies Zou Can’t Escape From (2021 Update)

While this film does not take place largely in jail, it is a byproduct of incarceration. Two brothers who are active in neo-Nazi and white supremacist movements appear in the film. After being imprisoned and reformed, the individual tries to protect his brother from further brainwashing by these harmful organizations. Not only is the film extremely popular, but it has also been utilized for educational reasons throughout the United States.

Derek Vinyard is a white supremacist gang leader and a skinhead. He is sentenced to three years in jail for murdering two black guys who attempted to steal his truck. Prison allows him to reflect on his life, and upon his release, he resolves to avoid the hatred and prejudice of his past. He disassociates himself from the group and seeks to live a regular life. His prior acts and biases, on the other hand, may have affected his younger brother.

21. 12 Monkeys (1995)

A claimant to be a time traveler from the distant year 2035, James Cole—a delusory prisoner in a 1990 mental institution—feels driven to carry out his vital mission: to save the world from a lethal viral agent capable of annihilating billions.

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However, when Cole’s psychiatrist, Dr. Kathryn Railly, begins to suspect that there is more to him than meets the eye, a fateful meeting with another inmate—the insane Jeffrey Goines—sets in motion a series of incomprehensible events, balancing the past and the present, sanity, and insanity. While all evidence now points to the radical activist group known simply as the Army of the Twelve Monkeys, is the reality Cole so eloquently depicts actual or is it only a distressing but subjective hallucination?

22. O Brother, Where Art Thou? (2000)

The film, loosely based on Homer’s “Odyssey,” follows Ulysses Everett McGill and his pals Delmar and Pete through their picaresque adventures in 1930s Mississippi.

They are sprung from a chain gang and are attempting to reach Everett’s house to collect the buried cash from a bank heist when they come face to face with a succession of odd people. Among them are sirens, a cyclops, bank robber George “Baby Face” Nelson (who is enraged by his moniker), a governor campaigning and his opponent, a KKK lynch mob, and a blind prophet who warns the three that “the riches you seek shall not be the treasure you find.”

23. Shot Caller (2017)

Jacob is enjoying the good life: a great profession and a loving family. However, his world is turned upside down when he is condemned to prison following a tragedy. On the inside, he immediately discovers that he must adjust to the prison system’s severe conditions. However, if Jacob is liberated, will he be able to find atonement or will his decisions lead to his demise?

24. Felon (2008)

Wade Porter, a family guy, is enjoying the American Dream with his fiancée Laura and their kid Michael: they own a lovely house, he has secured a loan to expand his business, and they are about to marry. Their fantasy becomes a nightmare, however, when Wade accidentally murders a burglar who came into their house in the middle of the night while mowing his lawn.

He is brought to trial and accepts the prosecutor’s plea bargain, receiving a three-year jail term. During the bus ride, an incident occurs, and Wade is falsely accused and transferred to the highest security wing, which is commanded by the unscrupulous Lieutenant Jackson. John Smith, Wade’s cellmate who was condemned to life in prison for avenging his family’s murder, befriends Wade, offers valuable counsel, and instills faith in Wade that he will return to his family.

25. Escape Plan: The Extractors (2019)

40 Best Prison Movies Zou Can’t Escape From (2021 Update)

Ray Breslin, the Houdini of breakouts, finds himself in the impregnable Latvian jail known as the “Devil’s Station” to recover Daya, the abducted daughter of a prominent Hong Kong computer billionaire.

Ray and his team—Hush, Trent DeRosa, and the businessman’s bodyguard, Bao—must penetrate the guarded property before the determined kidnapper begins murdering the captives. This time, though, it’s personal, and Ray now has an additional motive to win at any costs. Is it possible for the Extractors to make it happen?

26. Dead Man Walking (1995)

“Dead Man Walking” received four Academy Award nominations, including one for Susan Sarandon as Best Actress, one for Sean Penn as Best Actor, and one for Tim Robbins as Best Director.

On Death Row, a condemned killer and the nun who befriends him. The depiction of carefully drawn people and their interactions as the days, hours, and minutes count down to the condemned man’s death elicits strong emotions.

While Matthew Poncelet and Sister Prejean urgently seek a stay of execution from the governor or the courts, scenes from the heinous crime are intercut, eventually revealing the truth about what occurred. Along with her material assistance, the nun seeks to reach out spiritually and serve as a guide to salvation.

27. Sleepers (1996)

Four youngsters growing up in Hell’s Kitchen commit a prank that results in the death of an elderly man. Sentenced to no less than one year at the Wilkinson Center in upstate New York, the four friends undergo profound changes as a result of the beatings, humiliation, and sexual abuse they endure at the hands of the guards supposed to protect them. Thirteen years later, a chance encounter results in an opportunity for vengeance against the Wilkinson Center and its guards.

28. The Last Castle (2001)

When three-star General Irwin is transferred to a maximum security military prison, Colonel Winter, the prison’s warden, can’t help but admire the highly decorated and experienced soldier. Irwin has been demoted from his position but not from his renown for disobedience during a mission. Colonel Winter, who rules the jail with an iron hand, admires the General greatly but employs very different tactics to maintain discipline.

After a brief while, Irwin becomes aware of Winter’s inhumane treatment of the convicts. He intends to teach Winter a lesson by seizing control of the institution and removing his arrogant attitude. When Winter decides to join what he still considers to be a game, it may be too late to win.

29. The Rock (1996)

Eighty-one vacationers are taken captive by a gang of rogue Marine commandos who acquire a cache of chemical weapons. Their commander, a former highly decorated general, has demanded a ransom payment of one hundred million dollars as reparation to the families of Marines killed in clandestine missions and therefore denied compensation.

Alternatively, he has threatened to launch fifty rockets with lethal VX nerve gas onto the San Francisco Bay region. An elite S.E.A.L. team is created with the assistance of a Federal Bureau of Investigation chemical warfare expert (Stanley Goodspeed) and a previous Alcatraz escapee (John Patrick Mason) to breach the terrorists’ fortifications on Alcatraz and eliminate the rocket threat before time runs out.

30. The Escapist (2008)

40 Best Prison Movies Zou Can’t Escape From (2021 Update)

Frank Perry is a fourteen-year-old institutionalized prisoner serving a life sentence without parole. When his estranged daughter is diagnosed with a terminal illness, he is desperate to reconcile with her before it is too late. He devises an innovative escape strategy and joins a dysfunctional gang of escapists – misfits with specialized talents necessary for their daring scheme and bonded by their desire to escape their hell hole existence. Much of the action takes place beneath London’s tunnels, sewers, and underground rivers.

31. The Hurricane (1999)

Rubin Carter, a boxer who was wrongly convicted of a triple homicide in 1966, had his story immortalized in the 1975 Bob Dylan song “The Hurricane.” Carter was ultimately released in 1985, and Denzel Washington portrayed him in a film produced by Norman Jewison and based on the boxer’s biography, “The Sixteenth Round,” 14 years later.

This documentary chronicles the rise of Rubin “Hurricane” Carter, an African-American boxer who overcame a difficult upbringing to become a strong contender for the middle-weight boxing championship. His aspirations are dashed, however, when he is charged with triple murder and sentenced to three natural-life sentences. Despite becoming a cause celebre and his tenacious efforts to establish his innocence through his memoirs, he has become disillusioned after years of unsuccessful efforts.

This changes when an African-American youngster and his Canadian mentors read his book and become convinced enough of his innocence to strive for his exoneration. Hurricane and his friends quickly discover, however, that their struggle pits them against a racist system that has benefitted from this atrocity and has no intention of reversing it.

32. The Defiant Ones (1958)

The Defiant Ones is one of those well-intentioned, old-school analyses of American race relations that attributes racial tensions to “mutual hate” rather than to blazing, systemic white supremacy.

Two prisoners, John ‘Joker’ Jackson – who is white – and Noah Cullen – who is black – flee when the vehicle transporting them is sideswiped and driven off the road during a violent downpour. They despise one another, yet being tied together compels them to work together. Their objective is to drive 60 miles north to the location where Noah formerly worked and catch a train that Noah hopes is still operating on that route.

While the local Sheriff attempts to arrest them – despite the efforts of a well-intentioned but rather rule-obsessed and humorless State police captain – Joker and Noah establish an unusual relationship and a level of loyalty that is uncharacteristic of their circumstances.

33. The Old Man and the Gun (2018)

The film is based on David Grann’s New Yorker article on real-life serial jail escapee and career bank robber Forrest Tucker.

While he may not appear to be one, Forrest Tucker has spent his whole life as a criminal, an adept escape artist, and a skilled bank robber. Without a doubt, Tucker’s flawless plan is based on his perfect sense of dress, his steadfast conviction in never resorting to violence, being courteous, and robbing just enough money, always with a huge smile on his lips.

Then, following a successful heist, Forrest meets Jewel, a damsel in despair, and the two have an innocent romance. However, dedicated Forrest and his crew have already attracted the notice of Detective Hunt, who sets out on a quest to locate and apprehend the thieves. Is Tucker capable of renunciation his previous self and reforming for the sake of the good-hearted Jewel?

34. The Grand Budapest Hotel (2014)

The Grand Budapest Hotel, Wes Anderson’s most pastel film, is a master at recreating the many aesthetics of Weimar-era Eastern Europe, featuring a jail breakout scenario that is as amusing as it is nerve-wracking.

The Grand Budapest Hotel was formerly located in the remote regions of Eastern Europe, in the erstwhile Republic of Zubrowka. A writer recalls staying at the hotel during the off-season many years ago and the stories he learned about the property’s history from the elderly proprietor, Mr. Zero Moustafa (F. Murray Abraham). He informs the young writer about his acquisition of the hotel and the property’s original concierge, M. Gustave (Ralph Fiennes).

Young Zero (Tony Revolori) is a lobby boy at the time and accompanies Gustave to a will reading following the death of one of their frequent visitors. She leaves a priceless artwork to Gustave, but when the woman’s son contests the will, Gustave and Moustafa take the picture, precipitating a chain of events that culminates in Moustafa’s current situation.

35. The Fugitive (1993)

Dr. Richard Kimble, a well-known Chicago surgeon, has discovered that his wife, Helen, has been brutally killed in her own house. The police apprehended Kimble and charged him with murder. Then, Kimble was tried, convicted, and sentenced to death (without Justification). However, Kimble’s conveyance wrecked on the route to prison.

Kimble manages to evade capture and is now on the run. Kimble is pursued by Deputy Samuel Gerard of Chicago. Meanwhile, Kimble begins his inquiry to ascertain who murdered his wife and to ensnare Gerard and his crew as well.

36. A Man Escaped (1956)

Robert Bresson’s gripping jail escape thriller will raise your heart rate to dangerous levels. It follows an imprisoned French Resistance soldier, Lt. Fontaine (François Leterrier), as he attempts to escape from a Nazi concentration camp during WWII, scared and feeble.

Lieutenant Fontaine, a captured French Resistance soldier, awaits a definite death sentence for espionage in a desolate Nazi jail in Lyon, France. Faced with malnutrition and paralyzing dread, he must devise an incredible escape plan, compounded by the dilemma of who to trust and what lies outside the little part of the jail they are kept in.

37. American Me (1992)

While “American Me” is not an accurate portrayal of the Mexican Mafia’s power grab in the California Prison System during the 1950s and 1960s, it is a compelling narrative about Montoya Santana, a Los Angeles youngster who joins a gang and ends up spending the most of his life behind bars. Edward James Olmos directs and acts in the crime drama, which garnered positive reviews at Cannes but failed to generate enough money to cover its $16 million budget.

This epic depiction of thirty years of Chicano gang life in Los Angeles centers on a kid called Santana, who forms his gang with his buddies Mundo and the Caucasian-but-acting-Hispanic J.D. They are quickly imprisoned for a break-in. Santana re-enters problems and immediately transfers from reform school to jail, where he spends eighteen years and becomes the leader of a strong gang both within and outside the institution. When he is eventually released, he attempts to make sense of the violence in his life in a society that has changed significantly since he was last there.

38. I am a Fugitive from a Chain Gang (1932)

I Am a Fugitive from a Chain Gang is a depressing film from Hollywood’s early talkie years about an aimless WWI veteran (Paul Muni) who ends up ruining his entire life after robbing a bank—for which he is sentenced to prison, assigned to a chain gang, and eventually escapes—only to discover that, even once free, he has no future.

James Allen, a returning soldier who refuses to return to the old industrial grind, degenerates into a hobo. He gets railroaded into an extraordinarily cruel chain gang as a result of his innocent involvement in thievery. Finally fleeing, he finds success in the construction industry…and a greedy girlfriend Marie who threatens to expose him if he does not marry her. When he meets and falls in love with Helen, things spiral out of control.

39. Stir Crazy (1980)

Gene Wilder and Richard Pryor feature in “Stir Crazy” as two Hollywood aspirants who are falsely accused of bank robbery and sentenced to 125 years in prison. Of course, the two comics continue to cause havoc behind bars in this 1980 Sidney Poitier-directed comedy that earned more than $100 million domestically — more than any other picture directed by an African-American at the time.

Skip and Harry are arrested and imprisoned in a western jail after being falsely accused of bank robbery. The two eastern lads struggle to adjust to their new lives until the warden discovers Skip’s innate ability to ride broncos in time for the next inter-prison rodeo.

40. Kiss of the Spider Woman (1985)

“Kiss of the Spider Woman,” directed by Brazilian Héctor Babenco, is based on the 1976 Manuel Puig book of the same name. “Kiss of the Spider Woman,” a story of revolution, love, and treachery set in a Brazilian jail, earned rave reviews, and Hurt was nominated for an Academy Award and a BAFTA for his performance as transsexual convict Luis Molina.

Luis Molina and Valentin Arregui share a jail cell in South America. Luis, a transgender man, is convicted of immoral activity, while Valentin is imprisoned for political reasons. Luis creates love films to escape reality, while Valentin attempts to focus on the problem at hand. The two guys develop an understanding and respect for one another throughout their time together.

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