Movies Like History's Hardest Prisons: Debt and Damnation

If you liked History's Hardest Prisons: Debt and Damnation (2009), a documentary and history movie directed by David Wilson, 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
McQueen (2018)
★ 7.4/10Also documentary
Alexander McQueen's rags-to-riches story is a modern-day fairy tale, laced with the gothic. Mirroring the savage beauty, boldness and vivacity of his design, this documentary is an intimate revelation of McQueen's own…
2
The Unknown Known (2013)
★ 6.8/10Also documentary and history
Former United States Secretary of Defense Donald Rumsfeld discusses his career in Washington D.C. from his days as a congressman in the early 1960s to planning the invasion of Iraq in 2003.
3
Making Waves: The Art of Cinematic Sound (2019)
★ 6.9/10Also documentary and history
The history of cinematic sound, told by legendary sound designers and visionary filmmakers.
4
The Soviet Story (2008)
★ 7.3/10Also documentary and history
“The Soviet Story” is a story of an Allied power, which helped the Nazis to fight Jews and which slaughtered its own people on an industrial scale. Assisted by the West, this power triumphed on May 9th, 1945. Its…
5
Red Army (2015)
★ 7.4/10Also documentary and history
A documentary highlighting the Soviet Union's legendary and enigmatic hockey training culture and world-dominating team through the eyes of the team's Captain Slava Fetisov, following his shift from hockey star and…
6
13th (2016)
★ 7.8/10Also documentary
An in-depth look at the prison system in the United States and how it reveals the nation's history of racial inequality.
7
The Work (2017)
★ 7.5/10Also documentary
Set entirely inside Folsom Prison, The Work follows three men during four days of intensive group therapy with convicts, revealing an intimate and powerful portrait of authentic human transformation that transcends…
8
Maternal Instinct (2026)
★ 7.2/10Also documentary
Police pull over a woman who claims she just gave birth. But the baby — and the blood — aren't hers. Twisted lies unravel in this true-crime documentary.
9
Fuck (2006)
★ 6.4/10Also documentary
A documentary on the expletive's origin, why it offends some people so deeply, and what can be gained from its use.
10
9/11: Inside the President's War Room (2021)
★ 6.9/10Also documentary and history
Experience the events of September 11, 2001 through the eyes of President Bush and his closest advisors as they personally detail the crucial hours and key decisions from that historic day.
11
Cover-Up (2025)
★ 7.2/10Also documentary and history
He's devoted his career to uncovering stories the powerful want buried. From My Lai to Abu Ghraib, dig into the life's work of journalist Seymour Hersh.
12
The Untold History Of The United States (2012)
★ 8.2/10Also documentary and history
Oliver Stone charts the history of the United States from the Second World War to the present.
13
Come See Me in the Good Light (2025)
★ 7.1/10Also documentary
In an intimate and joyful story of love in the face of loss, celebrated poets Andrea Gibson and Megan Falley find strength—and unexpected hilarity—in what might be their final year together.
14
Ronaldo (2015)
★ 7/10Also documentary and history
Filmed over 14 months with unprecedented access into the inner circle of the man and the sport, this is the first official and fully authorised film of one of the most celebrated figures in football. For the first time…
15
Above Majestic (2018)
★ 7.4/10Also documentary
A look at the origins, history and conspiracies behind the "Majestic 12", a clandestine group of military and corporate figureheads charged with reverse-engineering extraterrestrial technology.
16
Capitalism: A Love Story (2009)
★ 7.1/10Also documentary and history
Michael Moore comes home to the issue he's been examining throughout his career: the disastrous impact of corporate dominance on the everyday lives of Americans (and by default, the rest of the world).
17
Elstree 1976 (2015)
★ 6.2/10Also documentary
A documentary about ten very different lives connected by having appeared onscreen wearing masks or helmets in Star Wars.
18
The Accountant of Auschwitz (2018)
★ 6.9/10Also documentary and history
Oskar Gröning, known as the "Accountant of Auschwitz," was charged with the murder of 300,000 Jews. When he took the stand in 2015, at the age of 94, his trial made headlines worldwide.
19
My Mom Jayne (2025)
★ 8/10Also documentary
Through deeply personal interviews with her siblings and an examination of the photographs, letters, and belongings left behind, Mariska assembles a new portrait of her mother Jayne Mansfield, an extraordinary and…
20
The Mystery of D.B. Cooper (2020)
★ 6.3/10Also documentary and history
This documentary brings to life the stories of four people believed by their family and friends to be “DB Cooper,” a man who hijacked a 727 flying out of Seattle and jumped from the plane over the wilds of Washington…