This Oscar-Nominated Movie Is Already One Of The Best Prison Films Ever Made

Bronson stars Tom Hardy as Michael Peterson, a tougher-than-nails guy who gets seven years in the slammer for robbing a jewelry store. It turns out that being in jail both suits him perfectly and doesn't suit him at all. Peterson has a penchant for picking fights with guards and fellow prisoners. That lands him in solitary confinement, where he shifts his personality, morphing into “Charles Bronson.” Letting his new identity out of solitary only leads to violence that escalates to a whole other level.

Hardy is magnificent in a tough role. Bronson is based on a true story, one that's hard to believe because it doesn't seem logical that someone could be so uncontrollably violent. The actor sidesteps that issue by making the character's twisted psychology come alive. Director Nicholas Winding Refn gives the picture a great, gritty style, while also staging the fighting sequences with the necessary brutality. All in all, this is a gripping portrait of a remarkably disturbed individual. 

Clint Eastwood made a career playing cops like Dirty Harry Callahan, so it's fun to see him on the other side of the law in Escape from Alcatraz. He plays Frank Morris, a criminal who is sent to Alcatraz prison because he's already broken out of several other jails. Of course, he fully intends to break out of this one, too, especially after clashing with the no-nonsense warden (Patrick McGoohan). He rallies a team of fellow cons to help him pull off a complex, daring escape.

Eastwood is typically good, and typically laconic, in Escape from Alcatraz. The secret to making a story like this work is having an antagonist who's just as interesting as the hero. McGoohan fulfills that requirement perfectly. The scene where the warden first meets Frank and lays down all the rules is a masterpiece of tone. Instead of coming off as stereotypically evil, he makes it powerfully, abundantly clear that he will give no leniency on anything. That makes us want to see Frank succeed. Crisp direction from Don Siegel keeps the tension mounting. 

Director Greg Kwedar's Sing Sing is an inspiring true story about the power of art and theater to bring hope and meaning to the lives of the prisoners at Sing Sing prison. Colman Domingo plays Divine G, a wrongfully convicted man who spends his time trying to win his release and leading the Rehabilitation Through the Arts program, in which incarcerated people put on Shakespeare plays.

While the movie is a beautiful tribute to the human spirit, it also does not shy away from the darker realities of life in prison and how dehumanizing the system can be. This combination makes it one of the most honest and emotionally impactful movies about prison life ever made.

Mark “Chopper” Read is a real person, known at one point as Australia's most notorious criminal. Eric Bana plays him in Chopper, a look at the hard life and times of this troubled man. His stint in prison is marked by violence. He intentionally violates rules set by two of the prison's gangs. He gets stabbed by his best friend and barely bats an eyelash. And when he wants to get transferred to a psychiatric unit, he arranges to have his own ears cut off.

Bana is chilling in the role, capturing Chopper's volatile temper and seeming lack of any kind of moral compass. The actor was known for comedy at the time, so the role marked a significant transition in his career. The back half of the movie finds Chopper out on the streets, but prison hovers over the story nonetheless, because we know that for as explosive as he is, time behind bars only made him more so. Few cinematic convicts are as terrifying as he is, thanks to Bana's extraordinary work. 

William Holden won an Academy Award for Billy Wilder's Stalag 17. He plays Sgt. Sefton, one of the prisoners in a German POW camp. He has an established reputation for making little deals with the guards. This leads him to become suspect #1 when two other prisoners are shot dead while attempting to escape. Somebody clearly ratted them out. Sefton proclaims his innocence and vows to find the real culprit, all while facing the wrath of his fellow detainees.

Holden's strong performance is obviously one of the movie's prime selling points. Beyond that, it has a screenplay that's darkly funny, as befitting Wilder. Including humor in a film set in a POW camp might sound sketchy, but the movie puts a lot of emphasis on human interactions and motivations, so there is an opportunity to laugh on that count. Wilder's direction is another highlight. He keeps the pace brisk, expertly balancing out the demands of the plot with his desire to dive into characterization. Stalag 17 is one of his finest works. 

Denzel Washington received an Oscar nomination as Best Actor for The Hurricane. It was the only nomination the film received, but that doesn't mean it isn't one of the most impactful films of 1999. The actor portrays Rubin "Hurricane" Carter, a former championship boxer who got three life sentences for a series of killings he did not commit. The film looks at his efforts to hold on to hope while a group of Canadians work to get his case overturned. 

Directed by Norman Jewison, The Hurricane features one of Washington's most finely-tuned performances. He brings passion, pride, and honor to Rubin Carter, along with a refusal to surrender his dignity. The details of how the Canadians worked tirelessly to clear Carter's name are like something out of an intricately scripted legal thriller. Of course, they succeeded in real life, and this dramatization of both their fight and Carter's insistence that God would lead him to freedom proves inspiring.