1. Con Air (1997)
When Piper (Taylor Schilling) is loaded into prison transport to be flown off to an unknown destination in the first episode of Season 2, she ends up meeting a genial fellow inmate named Lolly, played by Lori Petty. But when Nicolas Cage’s Cameron Poe boards a prison plane on his way to be released after serving time in Con Air, he’s not so lucky. This 1997 action flick might be the only Cage movie in which the weirdness of his performance (“Why couldn’t you put the bunny back in the box?”) is equalled by the fierce scenery chewing of his co-stars, including John Malkovich, Ving Rhames, Danny Trejo, Dave Chappelle, and Steve Buscemi.
2. Greenfingers (2000)
If you’re pining for more stories of gardening behind bars after Season 2’s introduction of Red’s (Kate Mulgrew) shed, this British comedy stars Clive Owen as Colin Briggs, a hardened prisoner who learns that his true calling is plants, and becomes a softer, friendlier human being in the process. Introduced to gardening by his cellmate, Colin ends up competing in the posh Hampton Court Palace Flower Show after attracting the attention and support of aristocratic celebrity gardener Georgina Woodhouse (Helen Mirren).
3. The Shawshank Redemption (1994)
Institutional corruption and the sadistic side of power is a theme in both Orange Is The New Black and The Shawshank Redemption, though Shawshank’s warden Samuel Norton (Bob Gunton) reveals himself to be far more of a monster under the pious exterior than anyone on the series (which presents a human side to all of its characters). But while Andy Dufresne’s (Tim Robbins) integrity and perseverance in the face of the warden’s hypocrisy and cruelty do eventually allow him to triumph, there’s no such clear-cut justice on the show, which suggests that everyone gets warped and compromised by the system.
4. Caged Heat (1974)
Women in prison stories used to be synonymous with exploitation films, like this 1970s feature distributed by schlock king Roger Corman’s New World Pictures. And that means sadistic wardens, predatory lesbians, and all the trashy stereotypes that Orange Is The New Black digs into and subverts. Written and directed by Jonathan Demme, Caged Heat was the Silence of the Lambs filmmaker’s debut, and contains its own satire of the genre along with some social commentary — as well as all the expected gratuitous nudity and over-the-top violence.
5. A Prophet (2009)
On the show, Piper’s transformation from naive newcomer to hardened “lone wolf” continues, but she’s got at least another season ahead of her before she’s running gangs and shanking rivals. This terrific French film doesn’t take nearly as long to show the journey of Malik El Djebena (Tahar Rahim) from timid fish to kingpin, but still feels epic. Nineteen years old and illiterate at the start, Malik learns the ropes and also learns about his heritage behind bars, becoming a power in his own right and challenging the Corsican mafia that initially used him as a pawn. A Prophet’s portrait of prison life depicts a vividly multicultural France of the sort that doesn’t usually show up on screen.
6. One Flew Over the Cuckoo’s Nest (1975)
Psych is a scary place in Orange Is The New Black — worse than SHU, which is saying something. But Mac McMurphy (Jack Nicholson) has to learn the hard way that the mental institution isn’t a comfier alternative to serving out his time in prison in One Flew Over the Cuckoo’s Nest. Mac installs himself as the ward’s leader, rallying the fellow patients and rebelling against the iron rule of Nurse Ratched (Louise Fletcher). But when you’re a prisoner, there’s an end to your sentence, whereas when you’re a patient, you’re there until you’re “better,” and Mac and Nurse Ratched differ in opinion on whether there’s anything he needs to be cured of.
7. Chopper (2000)
Like Orange Is The New Black creator and inspiration Piper Kerman, the late Mark “Chopper” Read wrote books about his prison experiences. But Chopper was far from the reformed dabbler in illegal activity that Kerman is — he was an outsized Australian who claimed to have killed 19 people. Andrew Dominik’s fictionalized film about Chopper’s life calls into question the glamour and prestige society can attach to notorious criminals, while centering on a breakout performance in the title role from Eric Bana, who was better known as a comedian at the time.
8. Escape from Alcatraz (1979)
The characters in Orange Is The New Black are in a minimum security prison serving out sentences that, for the most part, seem to be on the shorter side. Most are anxious to return to their lives and loved ones outside of Litchfield, so it’s taken until the second season for the idea of escape and becoming a fugitive to even really be raised. But for Frank Morris (Clint Eastwood), the prospect of escaping from the eponymous notorious island penitentiary is the only alternative to the crushing nature of living and possibly dying there. Based on a true story, Escape from Alcatraz is also an ode to inmate ingenuity, as Frank and his cohorts come up with a plan to break out.
9. I Love You Phillip Morris (2009)
Piper’s on-and-off, behind-bars, and before-them romance with Alex (Laura Prepon) continues to be a central part of her prison experience in Orange Is The New Black. The love story between con man Steven Jay Russell (Jim Carrey) and fellow inmate Phillip Morris (Ewan McGregor) in this 2009 movie is goofier, but no less fraught and dysfunctional. Steven’s deep and genuine feelings for the sweet-natured Phillip don’t stop him from compulsively lying and committing crimes, dragging the two of them in and out of jail to Phillip’s increasing distress.
10. Bronson (2008)
The more we see of the formidable Vee (Lorraine Toussaint), the major new addition to Orange Is The New Black in its second season who shakes up things for all the other inmates, the more it seems like some people are actually best suited for life behind bars. That’s also the case for the title character of Bronson, a career prisoner played by Tom Hardy. This fictionalized portrait of a real man, directed by Drive’s Nicolas Winding Refn, shows Bronson as someone who believes that being an unpredictable, violent criminal is his true calling.
11. The Experiment (2001)
Inspired by the Stanford prison experiment, Oliver Hirschbiegel’s film about what happens when 20 volunteers are hired by a psych professor to play guards and prisoners is an accelerated, extra-dark take on the abuses of power that Orange Is The New Black depicts so well. The Litchfield guards and administration may not go to the extremes of the character played by Justus von Dohnányi in The Experiment, but the themes remain the same — when people are stripped of rights, there’s nothing they can do to protect themselves, and the capacity for cruelty exists in everyone, especially when it carries no consequences.
12. Hunger (2008)
The hunger strike storyline in Season 2 of Orange Is The New Black is mostly played for laughs, even as it sends one character off to be force-fed against her will. Hunger, the first film from 12 Years A Slave director Steve McQueen, depicts the far more serious protest that was carried out by Bobby Sands (played by an excellent, pre-Magneto Michael Fassbender) and other Irish republican prisoners in 1981. A nearly dialogue-free first half shows the brutal conditions in the Maze Prison and the inmates’ resistance before the focus narrows in on Sands and the terrible physical toll of his decision.
13. Cool Hand Luke (1967)
The arrival of the babbling would-be activist Brook Soso (Kimiko Glenn) at Litchfield in Season 2 is an amusing play on someone who sees herself as Paul Newman in Cool Hand Luke, standing up to the system and rallying her fellow prisoners together, but who’s actually driving everyone nuts. Then again, Newman’s a lot more charming than the oblivious Soso in one of his iconic roles, confronting the Captain (Strother Martin), eating 50 hard-boiled eggs, and generally being one of the best-looking people to be part of a big screen chain gang.
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