Movies Like Principal Wood and the Detention Hall

If you liked Principal Wood and the Detention Hall (2006), a movie directed by Keith Miller, 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
Bad Sister (2015)
★ 6.6/10
As a top student at St. Adeline's Catholic Boarding School, Zoe senses that something is not quite right about the school's new nun-- a sense proven to be true when it is revealed the "good' nun is an imposter with a…
2
Brute Force (1947)
★ 7.3/10
Timeworn Joe Collins and his fellow inmates live under the heavy thumb of the sadistic, power-tripping guard Captain Munsey. Only Collins' dreams of escape keep him going, but how can he possibly bust out of Munsey's…
3
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.
4
Mr. Turner (2014)
★ 6.6/10
Eccentric British painter J.M.W. Turner lives his last 25 years with gusto and secretly becomes involved with a seaside landlady, while his faithful housekeeper bears an unrequited love for him.
5
Fedora (1978)
★ 6.7/10
Down-on-his-luck Hollywood producer Barry 'Dutch' Detweiler attempts to lure Fedora, a famous but reclusive film actress, out of retirement, only to discover the horrifying truth behind her success.
6
Convict (2014)
★ 6.5/10
Set in the dark and old Parramatta prison built by the original convicts our lead character Ray a war veteran finds himself serving 18 months for manslaughter after defending his fiance. He soon realizes that the…
7
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…
8
The Asphalt Jungle (1950)
★ 7.5/10
Recently paroled from prison, legendary burglar "Doc" Riedenschneider, with funding from Alonzo Emmerich, a crooked lawyer, gathers a small group of veteran criminals together in the Midwest for a big jewel heist.
9
Plunder Road (1957)
★ 6.9/10
A spectacular heist starts to unravel as the crooks take it on the lam.
10
Mickey's House of Villains (2002)
★ 7.3/10
The villains from the popular animated Disney films are gathered at the House of Mouse with plans to take over. Soon, the villains take over the house and kick out Mickey, Donald and Goofy. It's all up to Mickey and…
11
Nancy Drew and the Hidden Staircase (2019)
★ 6.3/10
Nancy Drew, a smart high schooler with a penchant for keen observation and deduction, stumbles upon the haunting of a local home. A bit of an outsider struggling to fit into her new surroundings, Nancy and her pals set…
12
From Straight A's to XXX (2017)
★ 5.9/10
When a change of circumstances leaves Miriam unable to pay her college tuition, she makes a surprising decision: to start performing in adult films, using the pseudonym Belle Knox. Miriam lies to her family and her…
13
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.
14
Step Up (2006)
★ 6.9/10
Delinquent Tyler Gage receives the opportunity of a lifetime after vandalizing a performing arts school, gaining him the chance to earn a scholarship and dance with up-and-coming dancer Nora.
15
The United States of Leland (2003)
★ 6.5/10
A withdrawn young man, Leland Fitzgerald is imprisoned for the murder of a mentally disabled boy, who also happened to be the brother of his girlfriend, Becky. As the community struggles to deal with the killing, Pearl…
16
Dog Pound (2010)
★ 7.2/10
Three juvenile delinquents arrive at a correctional center and are put under the care of an experienced guard.
17
My Policeman (2022)
★ 7.5/10
In the late 1990s, the arrival of elderly invalid Patrick into Marion and Tom’s home triggers the exploration of seismic events from 40 years previous: the passionate relationship between Tom and Patrick at a time when…
18
In the Blood (2014)
★ 5.8/10
When her husband goes missing during their Caribbean vacation, a woman sets off on her own to take down the men she thinks are responsible.
19
The Trouble with Angels (1966)
★ 6.7/10
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and…
20
The Odd Life of Timothy Green (2012)
★ 7/10
A childless couple bury a box in their backyard, containing all of their wishes for an infant. Soon, a child is born, though Timothy Green is not all that he appears.