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Movies like The Winslow Boy (1958)

The best movies like The Winslow Boy (1958) are The Duke (2021), The Madness of King George (1994) and Oslo (2021). If The Winslow Boy hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. The Duke (2021)

    In 1961, a 60-year-old taxi driver steals Goya’s portrait of the Duke of Wellington from the National Gallery in London. It was the first (and remains the only) theft in the Gallery’s history. What happens next becomes the stuff of legend.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  2. The Madness of King George (1994)

    Aging King George III of England is exhibiting signs of madness, a problem little understood in 1788. As the monarch alternates between bouts of confusion and near-violent outbursts of temper, his hapless doctors attempt the ineffectual cures of the day. Meanwhile, Queen Charlotte and Prime Minister William Pitt the Younger attempt to prevent the king's political enemies, led by the Prince of Wales, from usurping the throne.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  3. Oslo (2021)

    The true story of negotiations between implacable enemies — the secret back-channel talks, unlikely friendships and quiet heroics of a small but committed group of Israelis, Palestinians and one Norwegian couple that led to the 1993 Oslo Peace Accords.

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

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  4. Adventures of a Mathematician (2021)

    The warmhearted story of Polish immigrant and mathematician Stan Ulam, who moved to the U.S. in the 1930s. Stan deals with the difficult losses of family and friends all while helping to create the hydrogen bomb and the first computer.

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

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  5. Savage House (2026)

    Against the backdrop of 18th century England, a massive pox outbreak, and Jacobite uprising – Sir Chauncey Savage and Lady Savage blindly pursue a better life. It's not without a tinge of irony that their family name is the Savages, for this is a Savage House indeed, filled with duels, decadence, and bloodshed.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  6. Krush Groove (1985)

    Russell Walker is a young, successful manager of rap performers, handling acts for the Krush Groove label, including Run-DMC and The Fat Boys. When Run-D.M.C. has a hit record and Russell needs more money to press more copies, he borrows it from a street hustler and soon regrets his decision.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  7. Lady Windermere's Fan (1925)

    A society woman believes her husband is having an affair, a misconception which may have dire personal consequences for all involved.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  8. Oranges and Sunshine (2010)

    The story of Margaret Humphreys, a social worker from Nottingham, who uncovers one of the most significant social scandals in recent times – the forced migration of children from the United Kingdom to Australia and other Commonwealth countries. Almost singlehandedly, Margaret reunited thousands of families, brought authorities to account and worldwide attention to an extraordinary miscarriage of justice.

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

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  9. Radium Girls (2020)

    Young women toiling in a factory are exposed to hazardous material which takes a disastrous toll on their health.

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

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  10. Chloe and Theo (2015)

    A young woman, Chloe, living by her wits on the streets of New York City, has a chance meeting with a wise Inuit Eskimo, Theo, who was sent to New York by his elders to provide a message to the people of the world – We either change our destructive was or be destroyed by them. Chloe, who has been searching for something to believe in, becomes inspired by Theo and , with the help of a kind lawyer, Monica, the three of them present Theo’s story to the United Nations in hopes of creating a better future for all of us.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

  11. Giant (2026)

    Follows Prince Naseem Hamed from his humble beginnings on the tough working-class streets of Sheffield and his discovery by Ingle, himself a steel industry worker turned boxing trainer. Their unlikely partnership, Naz’s unorthodox style, cocky persona, and sheer dominance in the ring propelled them to the top of boxing’s elite and unprecedented levels of global superstardom, all in the face of the rampant Islamophobia and racism of ’80s and 90’s Britain.

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

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  12. Julia (1977)

    At the behest of an old and dear friend, playwright Lillian Hellman undertakes a dangerous mission to smuggle funds into Nazi Germany.

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

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  13. Munich - The Edge of War (2021)

    At the tense 1938 Munich Conference, former friends who now work for opposing governments become reluctant spies racing to expose a Nazi secret.

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

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  14. Tyler Perry's Madea's Family Reunion - The Play (2002)

    The fireworks begin when Madea’s family gathers for her granddaughter’s wedding. As usual, Madea rules the roost, as she and her neighbor, the wacky Mr. Brown, deliver nonstop laughs. Live, love, rejoice...it’s Madea’s Family Reunion!

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  15. Juniper (2021)

    When a self-destructive teenager is suspended from school and asked to look after his feisty alcoholic grandmother as a punishment, the crazy time they spend together turns his life around.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

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  16. Landline (2017)

    A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  17. Goltzius & the Pelican Company (2012)

    Hendrik Goltzius, a late-16th-century Dutch printer and engraver of erotic prints, seduces the Margrave of Alsace into paying for a printing press to make and publish illustrated books.

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

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  18. Treasure (2024)

    A music journalist accompanies her father, a charmingly stubborn Holocaust survivor, on a journey to his homeland. While she's eager to make sense of her family's past, her dad has an agenda of his own.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

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  19. For the Boys (1991)

    Talented USO entertainer Dixie Leonard and comedian Eddie Sparks deal with their relationship over the course of 5 decades from World War II to the Vietnam War era to their twilight era in the 90's.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

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  20. Grace of My Heart (1996)

    Philadelphia teenager Edna Buxton wins a talent contest during the early rock 'n' roll era, changes her name to Denise Waverly and moves to New York City to make it big. Though she flops as a recording artist, fast-talking record producer Joel Millner recognizes her songwriting talent and teams her with struggling songsmith Howard Caszatt.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

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  21. Trenck, der Pandur (1940)

    Film about the fictitious adventures of Franz Freiherr von Trenck, who lived during the times of empress Maria Theresia of Austria garnished with espionage and twisted love affairs.

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

  22. Chicago (2002)

    Murderesses Velma Kelly and Roxie Hart find themselves on death row together and fight for the fame that will keep them from the gallows in 1920s Chicago.

    Why it matches: Similar story and style · both comedy & drama

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  23. Pandora's Box (1929)

    The rise and inevitable fall of an amoral but naive young woman whose insouciant eroticism inspires lust and violence in those around her.

    Why it matches: Similar story and style · both drama

    Worth the HypeMovies like this
  24. A Few Good Men (1992)

    When cocky military lawyer Lt. Daniel Kaffee and his co-counsel, Lt. Cmdr. JoAnne Galloway, are assigned to a murder case, they uncover a hazing ritual that could implicate high-ranking officials such as shady Col. Nathan Jessep.

    Why it matches: Similar story and style · both drama

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  25. Curse of the Golden Flower (2006)

    During China's Tang dynasty the emperor has taken the princess of a neighboring province as his wife. She has borne him two sons and raised his eldest. Now his control over his dominion is complete, including the royal family itself.

    Why it matches: Similar story and style · both drama

    Worth the HypeMovies like this
  26. Čekanky (1940)

    Intern Plichta arrives to work at a country estate, where there is a strict ban on marriage for officials, issued by the count. However, Plichta meets Jiřina Krátká on the way, falls in love with her and intends to marry her. Adjunct Ptáček and intern Ráček are also vying for Jiřina. All the officials already have brides in mind, whom they call chicaneries. The news of the count's death causes a stir, and twelve merry-making parties are planned at the estate at once...

    Why it matches: Similar story and style · both comedy

  27. Closer (2004)

    The relationships of two couples become complicated and deceitful when the man from one couple meets the woman of the other.

    Why it matches: Similar story and style · both drama

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  28. Him and His Sister (1931)

    Postman Brabec is a welcome guest of the revue theatre for his sense of humor, and he brings his director Holt letters from female admirers every day. Holt's fans include Brabec's sister Anny. The girl would like to join the theatre, but for the time being works as a maid for the actress Velden. A new revue is being rehearsed, the name of the author is secret. Veldenová will return the role just before the premiere because she doesn't like it. The quick-witted Brabec introduces the director to his sister, who knows all the parts by heart.

    Why it matches: Similar story and style · both comedy

  29. His Majesty's Adjutant (1933)

    Lieutenant Patera, who unfortunately became involved in a scandalous affair in the highest circles of the Habsburg monarchy, is transferred from his sentence to the backwater garrison in Munich.

    Why it matches: Similar story and style · both comedy

  30. I‘ll Marry Off My Wife (1941)

    The film is about a slightly crazy botany professor Ducánek, who is so busy with his scientific experiments that he has completely forgotten that he is married. Neither his housekeeper Veronika nor his friend Potužník knew about the existence of his capricious wife, the operetta diva Lucy. However, when his wife returns home after seven years in remorse, Ducánek takes a complicated action to elegantly get rid of his wife...

    Why it matches: Similar story and style · both comedy

Like The Winslow Boy and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like The Winslow Boy?

The closest matches to The Winslow Boy are The Duke (2021), The Madness of King George (1994) and Oslo (2021). Below are 27 more, each with the reason it matches.

What should I watch after The Winslow Boy?

Start with The Duke (2021), the closest match to The Winslow Boy.

What is the highest-rated movie like The Winslow Boy?

A Few Good Men (1992), rated 7.6/10 by 4,417 TMDB users.

What is the newest movie like The Winslow Boy?

Savage House (2026) is the most recent release on this list.

Are there English movies like The Winslow Boy?

Yes: The Duke (2021), The Madness of King George (1994) and Oslo (2021).

How are movies similar to The Winslow Boy chosen?

First come films that Trakt’s viewers watch alongside The Winslow Boy, 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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