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Movies Like The Winslow Boy

If you liked The Winslow Boy (1948), a drama movie directed by Anthony Asquith, 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. 1The Winslow Boy

    The Winslow Boy (1999)

    ★ 6.8/10Also drama

    In pre-WWI England, a youngster is expelled from a naval academy over a petty theft, but his parents raise a political furor by demanding a trial.

  2. 2Oliver!

    Oliver! (1968)

    ★ 7/10Also drama

    Musical adaptation of Charles Dickens' Oliver Twist, a classic tale of an orphan who runs away from the workhouse and joins up with a group of boys headed by the Artful Dodger and trained to be pickpockets by master…

  3. 3Living

    Living (2022)

    ★ 7/10Also drama

    London, 1953. Mr. Williams, a veteran civil servant, is an important cog within the city's bureaucracy as it struggles to rebuild in the aftermath of World War II. Buried under paperwork at the office and lonely at…

  4. 4Night and the City

    Night and the City (1950)

    ★ 7.5/10Also drama

    Londoner Harry Fabian is a second-rate con man looking for an angle. After years of putting up with Harry's schemes, his girlfriend, Mary, becomes fed up when he taps her for yet another loan.

  5. 5What Maisie Knew

    What Maisie Knew (2013)

    ★ 7.1/10Also drama

    In New York City, six-year-old Maisie is caught in the middle of a bitter custody battle between her self-absorbed parents—an aging rock singer mother and a distracted art dealer father. As both quickly marry new…

  6. 6Won't Back Down

    Won't Back Down (2012)

    ★ 6.2/10Also drama

    Jamie Fitzpatrick and Nona Alberts are two women from opposites sides of the social and economic track, but they have one thing in common: a mission to fix their community's broken school and ensure a bright future for…

  7. 7Hamlet

    Hamlet (2009)

    ★ 7.3/10Also drama

    David Tennant stars in a film of the Royal Shakespeare Company's award-winning production of Shakespeare's great play. Director Gregory Doran's modern-dress production was hailed by the critics as thrilling…

  8. 8Newsies

    Newsies (1992)

    ★ 6.7/10Also drama

    A week in the life of the exploited, child newspaper sellers in turn-of-the-century New York. When their publisher, Joseph Pulitzer, tries to squeeze a little more profit out of their labours, they organize a strike…

  9. 9Blue Chips

    Blue Chips (1994)

    ★ 6.1/10Also drama

    Pete Bell, a college basketball coach is under a lot of pressure. His team isn't winning and he cannot attract new players. The stars of the future are secretly being paid by boosters. This practice is forbidden in the…

  10. 10Coach Carter

    Coach Carter (2005)

    ★ 7.6/10Also drama

    Based on a true story, in which Richmond High School head basketball coach Ken Carter made headlines in 1999 for benching his undefeated team due to poor academic results.

  11. 11Peterloo

    Peterloo (2018)

    ★ 6.7/10Also drama

    An epic portrayal of the events surrounding the infamous 1819 Peterloo Massacre, where a peaceful pro-democracy rally at St Peter’s Field in Manchester turned into one of the bloodiest and most notorious episodes in…

  12. 12Belle

    Belle (2013)

    ★ 7.1/10Also drama

    Dido Elizabeth Bell, the illegitimate, mixed-race daughter of a Royal Navy admiral, plays an important role in the campaign to abolish slavery in England.

  13. 13Hamilton

    Hamilton (2025)

    ★ 7.8/10Also drama

    Presenting the tale of American founding father Alexander Hamilton, this filmed version of the original Broadway smash hit is the story of America then, told by America now.

  14. 14Finding Neverland

    Finding Neverland (2004)

    ★ 7.3/10Also drama

    During a writing slump, playwright J.M. Barrie meets a widow and her four children, all young boys—who soon become an important part of Barrie’s life and the inspiration that lead him to create his masterpiece. Peter…

  15. 15Denial

    Denial (2016)

    ★ 6.8/10Also drama

    Acclaimed writer and historian Deborah E. Lipstadt must battle for historical truth to prove the Holocaust actually occurred when David Irving, a renowned denier, sues her for libel.

  16. 16Oliver Twist

    Oliver Twist (2005)

    ★ 6.8/10Also drama

    An orphan endures a harsh life in a workhouse before fleeing to London, where he falls in with a gang of juvenile pickpockets led by the criminal Fagin, and eventually finds a better life, exposing the cruelties of…

  17. 17Skin

    Skin (2009)

    ★ 6.4/10Also drama

    Based on the true story of a black girl who was born to two white Afrikaner parents in South Africa during the apartheid era.

  18. 18Blackmail

    Blackmail (1929)

    ★ 6.5/10Also drama

    London, 1929. Frank Webber, a very busy Scotland Yard detective, seems to be more interested in his work than in Alice White, his girlfriend. Feeling herself ignored, Alice agrees to go out with an elegant and…

  19. 19Fast Girls

    Fast Girls (2012)

    ★ 6/10Also drama

    A street smart runner develops an intense rivalry with an equally ambitious wealthy young athlete.

  20. 20A Taste of Honey

    A Taste of Honey (1961)

    ★ 7.1/10Also drama

    While out to avoid spending time with her narcissistic and promiscuous mother, sixteen-year-old Jo has a brief affair that leaves her pregnant and abandoned. When her mother remarries, Jo's only support becomes her…

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