Movies Like Penal Pen Pals

If you liked Penal Pen Pals (1999), a movie directed by Edward James, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
King Cobra (2016)
★ 5.8/10
It’s 2006, YouTube is in its infancy, and internet porn is still behind a paywall. Taking the stage name Brent Corrigan, a fresh-faced, wannabe adult video performer is molded into a star by Stephen, a closeted gay…
2
X-Rated 2: The Greatest Adult Stars of All Time (2016)
★ 6.8/10
Documentary sequel that offers a close-up look into the personal lives of the legendary porn stars who've survived the test of time and influenced popular culture. Blends rare interviews with erotic clips and…
3
Kiss of the Spider Woman (1985)
★ 7/10
The story of two radically different men thrown together in a Latin American prison cell. One is Valentin, a journalist being tortured for his political beliefs. The other is Molina, a gay window-dresser who fills…
4
Don Jon (2013)
★ 6/10
A New Jersey guy dedicated to his family, friends, and church, develops unrealistic expectations from watching porn and works to find happiness and intimacy with his potential true love.
5
Big Stan (2007)
★ 6.7/10
A weak con man panics when he learns he's going to prison for fraud. He hires a mysterious martial arts guru who helps transform him into a martial arts expert who can fight off inmates who want to hurt or love him.
6
Horrible Bosses 2 (2014)
★ 6.2/10
Dale, Kurt and Nick decide to start their own business but things don't go as planned because of a slick investor, prompting the trio to pull off a harebrained and misguided kidnapping scheme.
7
Barely Legal (2003)
★ 5.9/10
Teenager Deacon works at a video shop, and his buddies, Fred and Matt, sell the bootleg porno films he acquires. Deacon gets fired, but the pals have the bright idea of filming their own Internet porn flick in order to…
8
Lovelace (2013)
★ 6/10
Story of Linda Lovelace, who is used and abused by the porn industry at the behest of her coercive husband, before taking control of her life.
9
Porno (2019)
★ 6/10
When a group of naive teens working at a movie theater in a small Christian town discover a mysterious film hidden in its basement, they unleash an alluring succubus who gives them a sex education…written in blood.
10
The Longest Yard (1974)
★ 6.7/10
A football player-turned-convict organizes a team of inmates to play against a team of prison guards. His dilemma is that the warden asks him to throw the game in return for an early release, but he is also concerned…
11
The Shawshank Redemption (1994)
★ 8.7/10
Imprisoned in the 1940s for the double murder of his wife and her lover, upstanding banker Andy Dufresne begins a new life at the Shawshank prison, where he puts his accounting skills to work for an amoral warden…
12
X-Rated: The Greatest Adult Movies of All Time (2015)
★ 6.4/10
The evolution of adult cinema through the most influential films in history, a journey that begins in the 1970s and ends nowadays. An in-depth analysis of the success of the most prestigious erotic films, their impact…
13
Wasteman (2026)
★ 7.3/10
Taylor's hopes for a fresh start post-parole are jeopardised by cellmate Dee's arrival. As Dee takes Taylor under his wing, a vicious attack tests their bond, forcing Taylor to choose between protecting Dee and his own…
14
Jamesy Boy (2014)
★ 6.4/10
Based on the true story of teenager James Burns who goes from a suburban street gang to a maximum-security prison cell surrounded by hardened criminals. He turns his life around in prison thanks to the unexpected…
15
The Longest Yard (2005)
★ 6.7/10
Disgraced pro football quarterback Paul Crewe lands in a Texas federal penitentiary, where manipulative Warden Hazen recruits him to advise the institution's football team of prison guards. Crewe suggests a tune-up…
16
The Unforgivable (2021)
★ 7.4/10
A woman is released from prison after serving a sentence for a violent crime and re-enters a society that refuses to forgive her past.
17
Bringing Down the House (2003)
★ 6/10
Uptight lawyer Peter Sanderson wants to dive back into dating after his divorce and has a hard time meeting the right women. He tries online dating and lucks out when he starts chatting with a fellow lawyer. The two…
18
The Cable Guy (1996)
★ 6/10
When recently single Steven moves into his new apartment, cable guy Chip comes to hook him up—and doesn't let go. Initially, Chip is just overzealous in his desire to be Steven's pal, but when Steven tries to end the…
19
Buffalo '66 (1998)
★ 7.1/10
Billy is released after five years in prison. In the next moment, he kidnaps teenage student Layla and visits his parents with her, pretending she is his girlfriend and they will soon marry.
20
City Island (2009)
★ 6.9/10
The Rizzos, a family who doesn't share their habits, aspirations, and careers with one another, find their delicate web of lies disturbed by the arrival of a young ex-con brought home by Vince, the patriarch of the…