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Movies like Henry VIII & Trump: History Repeating? (2020)

The best movies like Henry VIII & Trump: History Repeating? (2020) are 9/11: Inside the President's War Room (2021), The Princess (2022) and Cover-Up (2025). If Henry VIII & Trump: History Repeating? hooked you with its documentary and history, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. 9/11: Inside the President's War Room (2021)

    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.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Popcorn FlickMovies like this
  2. The Princess (2022)

    Decades after her untimely death, Princess Diana continues to evoke mystery, glamour, and the quintessential modern fairy tale gone wrong. As a symbol of both the widening fissures weakening the British monarchy and the destructive machinery of the press, the Princess of Wales navigated an unparalleled rise to fame and the corrosive challenges that came alongside it. Crafted entirely from immersive archival footage and free from the distraction of retrospective voices, this hypnotic and audaciously revealing documentary takes a distinctive formal approach, allowing the story of the People’s Princess to unfold before us like never before.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Popcorn FlickMovies like this
  3. Cover-Up (2025)

    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.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Worth the HypeMovies like this
  4. The Unknown Known (2013)

    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.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Popcorn FlickMovies like this
  5. The Untold History Of The United States (2012)

    Oliver Stone charts the history of the United States from the Second World War to the present.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Absolute CinemaMovies like this
  6. Making Waves: The Art of Cinematic Sound (2019)

    The history of cinematic sound, told by legendary sound designers and visionary filmmakers.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Popcorn FlickMovies like this
  7. The War Room (1993)

    A behind-the-scenes documentary about the Clinton for President campaign, focusing on the adventures of spin doctors James Carville and George Stephanopoulos.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Popcorn FlickMovies like this
  8. The Green Book: Guide to Freedom (2019)

    In 1936, Victor H. Green (1892-1960) published The Negro Motorist Green Book, a book that was both a travel guide and a survival manual, to help African-Americans navigate safe those regions of the United States where segregation and Jim Crow laws were disgracefully applied.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Worth the HypeMovies like this
  9. The Black Power Mixtape 1967-1975 (2011)

    Examines the evolution of the Black Power Movement in US society from 1967 to 1975. It features footage of the movement shot by Swedish journalists in the United States during that period and includes the appearances of Angela Davis, Bobby Seale, Huey P. Newton, Eldridge Cleaver, and other activists, artists, and leaders central to the movement.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Worth the HypeMovies like this
  10. Apollo: Missions to the Moon (2019)

    National Geographic's riveting effort recounts all 12 crewed missions using only archival footage, photos and audio.

    Why it matches: Recommended by TMDB viewers · both documentary & history

    Worth the HypeMovies like this
  11. My Mom Jayne (2025)

    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 complex woman.

    Why it matches: Recommended by TMDB viewers · both documentary

    Absolute CinemaMovies like this
  12. Come See Me in the Good Light (2025)

    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.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  13. Avatar: The Deep Dive - A Special Edition of 20/20 (2022)

    An inside look at one of the most anticipated movie sequels ever with James Cameron and cast.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  14. I Am Heath Ledger (2017)

    The life and career of an actor, artist, and icon. His own journey through his own camera.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  15. Boys State (2020)

    This raucous journey into the heart of democracy captures an unusual rite of passage: 1,100 teenage boys from across Texas coming together to build a representative government from the ground up.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  16. As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000)

    A compilation of over 30 years of private home movie footage shot by Lithuanian-American avant-garde director Jonas Mekas, assembled by Mekas "purely by chance", without concern for chronological order.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  17. Shawn Mendes: In Wonder (2020)

    A portrait of singer-songwriter Shawn Mendes' life, chronicling the past few years of his rise and journey.

    Why it matches: Recommended by TMDB viewers · both documentary

    Absolute CinemaMovies like this
  18. Fuck (2006)

    A documentary on the expletive's origin, why it offends some people so deeply, and what can be gained from its use.

    Why it matches: Recommended by TMDB viewers · both documentary

    Popcorn FlickMovies like this
  19. Get Me Roger Stone (2017)

    From his days of testifying at the Watergate hearings to advising recent presidential candidate Donald Trump, Roger Stone has long offended people on both sides of the political fence as a force in conservative America. Outspoken author, pundit, ahead of his time election strategist, this is his story.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  20. Lewis Capaldi: How I'm Feeling Now (2023)

    An intimate, all-access documentary that will chronicle Lewis Capaldi's journey from a scrappy teen with a viral performance to a Grammy-nominated pop star.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  21. Plutocracy III: Class War (2017)

    The early struggles of the working class are placed under a microscope in Plutocracy III: Class War, the latest chapter in an exceptionally well produced series which explores the origins of America's growing economic divide.

    Why it matches: Similar story and style · both history & documentary

  22. Postcard (Or, from afar, you are a mirage) (2024)

    "The palm trees on the reverse are a delusion; so is the pink sand". This line, taken from a poem by Margaret Atwood, lights the path traced in "Postcard". As the years go by, landscapes transform, take on new meanings, and hold onto joys that will never be regained. The sea and the beach, once stages of happy summers, romances, and encounters, will turn into concentration camps or centers of detention and torture. This occurs across different times and places. In this piece, I embark on a journey through some of my works that explore the relationship between testimony, spaces, and time, engaging in dialogue with the beautiful film directed by Alejandro Segovia in 1972.

    Why it matches: Similar story and style · both documentary

  23. Syria's Woman at the Top (2026)

    Lyse Doucet speaks to Hind Kabawat, Syria's minister for social affairs and labour and the only female minister in the transitional government.

    Why it matches: Similar story and style · both documentary

  24. Blood Amber (2017)

    Somewhere in Myanmar is a forest rich in amber and controlled by the Kachin Independence Army (KIA). Most of its inhabitants work in a mine, digging the earth night and days in the hope of finding the precious ore that will get them out of poverty. But on top of the excruciating hardship of the work, they also have to fear an attack from the army.

    Why it matches: Similar story and style · both documentary

  25. Pouvoir Oublier (2025)

    Pouvoir Oublier is a political documentary first constructed from the words of the speakers whose lives changed on the tragic day of May 10, 1972 in Sept-Îles. Their word will be juxtaposed with archival material from the events, some of which are unpublished, which will reflect the collective euphoria in which Sept-Îles and all of Quebec were then bathed.

    Why it matches: Similar story and style · both documentary

  26. Stockholm Bloodbath (2024)

    In 1520, the notorious and power-hungry Danish King Christian II is determined to seize the Swedish crown from Sten Sture, no matter what it takes. Meanwhile, sisters Freja and Anne make a solemn promise to seek revenge on the men who brutally murdered their family. Everything comes to a head in the heart of Stockholm, where the sisters are drawn into a ruthless political struggle between Sweden and Denmark that culminates in a mass execution, presided over by the mad King "Christian the Tyrant," known as the Stockholm Bloodbath.

    Why it matches: Similar story and style · both history

    Popcorn FlickMovies like this
  27. 49 Up (2006)

    49 Up is the seventh film in a series of landmark documentaries that began 42 years ago when UK-based Granada's World in Action team, inspired by the Jesuit maxim "Give me the child until he is seven and I will give you the man," interviewed a diverse group of seven-year-old children from all over England, asking them about their lives and their dreams for the future. Michael Apted, a researcher for the original film, has returned to interview the "children" every seven years since, at ages 14, 21, 28, 35, 42 and now again at age 49.In this latest chapter, more life-changing decisions are revealed, more shocking announcements made and more of the original group take part than ever before, speaking out on a variety of subjects including love, marriage, career, class and prejudice.

    Why it matches: Similar story and style · both documentary

    Worth the HypeMovies like this
  28. Bethune: The Making of a Hero (1993)

    True story of Norman Bethune, a medical doctor who fought for justice in China during Mao's rise to power.

    Why it matches: Similar story and style · both history

  29. Persecution Blues: the Battle for the Tote! (2011)

    In 2010, the iconic Tote Hotel – last bastion of Melbourne’s vibrant music counterculture – was forced to close by unfair laws. Filmed over 7 years, “Persecution Blues” depicts the struggle of more than 20,000 fans – and the bands who inspire them – to preserve their history and protect their future, and puts the audience on the front line of an epic-scale culture war.

    Why it matches: Similar story and style · both documentary

  30. The End of America (2008)

    Based on her book of the same name, Naomi Wolf presents controversial evidence that America has begun a frightening descent into dictatorship and fascism. American democracy, as we know it, is under attack. By examining the chilling parallels between the current state of our nation and the ascent of dictators and fascism in other once-free societies, Wolf urges viewers to open their eyes to the horrors that lie ahead. From the increased use of paramilitary groups to the construction of secret prisons and the targeted suspension of the rule of law, the warning signs are all there for people to wake up and finally take notice.

    Why it matches: Similar story and style · both documentary

Like Henry VIII & Trump: History Repeating? and something else?

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Frequently asked questions

What are the best movies like Henry VIII & Trump: History Repeating??

The closest matches to Henry VIII & Trump: History Repeating? are 9/11: Inside the President's War Room (2021), The Princess (2022) and Cover-Up (2025). Below are 27 more, each with the reason it matches.

What should I watch after Henry VIII & Trump: History Repeating??

Start with 9/11: Inside the President's War Room (2021), the closest match to Henry VIII & Trump: History Repeating?.

What is the highest-rated movie like Henry VIII & Trump: History Repeating??

I Am Heath Ledger (2017), rated 7.4/10 by 233 TMDB users.

What is the newest movie like Henry VIII & Trump: History Repeating??

Syria's Woman at the Top (2026) is the most recent release on this list.

Are there English movies like Henry VIII & Trump: History Repeating??

Yes: 9/11: Inside the President's War Room (2021), The Princess (2022) and Cover-Up (2025).

How are movies similar to Henry VIII & Trump: History Repeating? chosen?

First come films that Trakt’s viewers watch alongside Henry VIII & Trump: History Repeating?, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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