5 Best Prison TV Shows Of All Time, Ranked

While it may not be as glamorous as mobsters or dragons, prison can make for some pretty compelling television. Incarceration is always a ripe source of conflict, especially when a bunch of flawed and angry characters are all cooped up together in the same oppressive space.

We've decided to compile the five best prison TV shows of all time. To determine which TV shows would make the cut, we examined reviews, Rotten Tomatoes scores, and awards. As well, we've also factored in their impact on the industry, the uniqueness of their premises, and the good old-fashioned entertainment value they provide. Basically, these are five prison shows you won't want to miss. If every prison show that was ever made got into a brawl in the prison yard, then these ones would probably come out on top.

• Cast: Benicio Del Toro, Patricia Arquette, Paul Dano
• Show Creator(s): Brett Johnson, Michael Tolkin
• Rating: TV-MA
• Aired: 2018
• Rotten Tomatoes Score: 89%
• Where to Watch: Paramount+

If you thought Ben Stiller only directed outrageous comedies like "Tropic Thunder," this prison drama will show you what a wide range he has. "Escape at Dannemora" stands out from the competition because it's inspired by a true story almost too bizarre to believe. In this show, two inmates (Benicio Del Toro and Paul Dano) escape from a maximum security prison by tunneling through the walls, thanks to the help of the prison seamstress (Patricia Arquette) who smuggles them tools and equipment inside frozen meat – all while having a passionate affair with both men.

"Escape from Dannemora" is a deliciously twisted tale starring deliciously twisted characters. Benicio Del Toro and Paul Dano are perfectly cast as the charismatic Matt and the hard-working Sweat, respectively. Meanwhile, Arquette's Tilly is a fascinating character, a seemingly-innocent character who demonstrates a shocking capacity for manipulation. "Escape at Dannemora" is well-crafted and cinematic in a way few TV shows are. This slow-burn series takes a while to get going, but once the daring escape unfolds, it is well worth the wait.

• Cast: Riz Ahmed, John Turturro, Bill Camp
• Show Creator(s): Richard Price, Steven Zaillian
• Rating: TV-MA
• Aired: 2016
• Rotten Tomatoes Score: 94%
• Where to Watch: HBO Max

Most prison shows give readers a clear idea of who the main character is and why they're in prison – either they're guilty, or they're innocent. But in "The Night Of," not even the protagonist knows the answer to that question. In this TV show, Pakistani-American Naz (Riz Ahmed) wakes up after a drug-induced haze to find the girl beside him brutally murdered. For law enforcement, it seems obvious Naz is guilty, so he is sent to Rikers Island prison to await trial. For Naz, who has no memory of that night, it is not so simple. Repeatedly throughout the show, both Naz and the viewers wonder if maybe he could have committed the murder.

"The Night Of" is beautifully shot and engrossing. Riz Ahmed rightfully won an Emmy Award for his portrayal of a man who is transformed by his time in prison. His co-star John Turturro crafts an instantly iconic character in Stone, the defense lawyer with eczema who can't resist looking after strays (figuratively and literally). What makes the series so unique is the way it constantly keeps audiences guessing. The ending of "The Night Of" never conclusively answers the question of Naz's innocence, leaving viewers to ponder that for themselves.

• Cast: Ernie Hudson, Terry Kinney, J.K. Simmons, Lee Tergesen
• Show Creator(s): Tom Fontana
• Rating: TV-MA
• Aired: 1997-2003
• Rotten Tomatoes Score: 93%
• Where to Watch: HBO Max

HBO's first hour-long drama series changed television forever. "Oz" follows the inmates of Oswald Maximum Security Prison, better known as "Oz" or "The Emerald City." The series rounds up an amazing cast, including Edie Falco, Christopher Meloni, and Rita Moreno. In particular, J.K. Simmons is unforgettable as the sadistic Vern Schillinger, while Harold Perrineau anchors the show with his frank monologues. It's a credit to the series that it manages to juggle the stories of so many different warring factions in the prison and give equal hearing to each.

Make no mistake, "Oz" is not for the faint of heart. This gritty series features a shocking amount of violence and misery. But as the show unfolds, it proves that it's got substance, too. "Oz" has plenty to say about toxic masculinity, our justice system, and our society. This HBO show's realism and willingness to tackle uncomfortable themes head-on are unrivaled. Dare we say it, "Oz" is so groundbreaking that almost every major Prestige TV show, from "The Sopranos" to "Game of Thrones," owes it a debt.

• Cast: Taron Egerton, Paul Walter Hauser, Greg Kinnear, Ray Liotta
• Show Creator(s): Dennis Lehane
• Rating: TV-MA
• Aired: 2022
• Rotten Tomatoes Score: 98%
• Where to Watch: Apple TV

Another prison show based on a true story, "Black Bird" is a must-see. When Jimmy Keene (Taron Egerton) faces 10 years in prison, he is offered a way out. If he can befriend serial killer Larry Hall (Paul Walter Houser) in prison and get him to confess to his murders, Keene will be released, knowing that he has stopped a killer from walking free. So Keene must navigate a dangerous dance with a serial killer who could see through his act at any moment.

It's actually incredible how many details from the show were drawn straight from real life, from the FBI agent posing as Keene's girlfriend so she could visit him in prison, to the moment Keene attacks a fellow inmate for turning off the TV. Fans who watch this show can marvel at two talented actors at the top of their game. It's fascinating, watching Taran Egerton walk the tightrope between playing two very different roles: the tough-guy persona Keene adopts in the presence of Larry, and the man underneath who knows he is trapped in a cage with a monster. Meanwhile, Paul Walter Hauser went to great lengths to get inside the head of this serial killer, even capturing his distinctive high-pitched voice. The result is a performance that's downright chilling (even if the intense experience left Paul Walter Hauser in tears).

• Cast: Taylor Schilling, Kate Mulgrew, Uzo Aduba, Danielle Brooks, Taryn Manning
• Show Creator(s): Jenji Kohan
• Rating: TV-MA
• Aired: 2013-2019
• Rotten Tomatoes Score: 90%
• Where to Watch: Netflix

Perhaps the best prison show of all time is "Orange Is the New Black." Based on the autobiography about the author's experience in a woman's prison, "Orange is the New Black" follows Piper (Taylor Shilling), the naive new girl who believes she doesn't belong in prison. Over the course of seven seasons, Piper not only accepts her place among the inmates but embraces it and stands in solidarity with them. The series boasts an absolutely stacked cast, with more outstanding performances than we could possibly name here (though we'd like to give a shout-out to Danielle Brooks, Uzo Adoba, and Natasha Lyonne).

Nominated for Emmy Awards both as a comedy and a drama, "Orange Is the New Black" combines the best of both worlds. The chemistry between the ladies in prison carries much the same warmth of the cast of a classic sitcom, and humor blooms in unexpected places in this show. Yet "Orange Is the New Black" also doesn't shy away from the tragic stories of these characters and the unfairness of the institution. "Orange is the New Black" is more realistic and more human than almost any other prison show. Nothing better exemplifies the show's authenticity than its opening credits. The title sequence features not the show's cast but instead photos of real-life inmates, reminding viewers that this is far more than just Piper's story.