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Movies Like The Winslow Boy

If you liked The Winslow Boy (1999), a drama movie directed by David Mamet, 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. 1What 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…

  2. 2Won'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…

  3. 3The Rainmaker

    The Rainmaker (1997)

    ★ 7/10Also drama

    Fresh out of law school and desperate for work, idealistic rookie Rudy Baylor takes on a powerful insurance company accused of denying a dying boy’s claim. Teaming up with a scrappy, unlicensed paralegal, he finds…

  4. 4Hamilton

    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.

  5. 5Night 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.

  6. 6On the Basis of Sex

    On the Basis of Sex (2018)

    ★ 7.3/10Also drama

    Young lawyer Ruth Bader Ginsburg teams with her husband Marty to bring a groundbreaking case before the U.S. Court of Appeals and overturn a century of sex discrimination.

  7. 7Living

    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…

  8. 8Skin

    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.

  9. 9Hamlet

    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…

  10. 10Gigi & Nate

    Gigi & Nate (2022)

    ★ 7.6/10Also drama

    A young man with a bright future suffers a near-fatal accident and recreates his new life with the help of an unlikely animal friend.

  11. 11Coach 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.

  12. 12Dead Poets Society

    Dead Poets Society (1989)

    ★ 8.3/10Also drama

    At an elite, old-fashioned boarding school in New England, a passionate English teacher inspires his students to rebel against convention and seize the potential of every day, courting the disdain of the stern…

  13. 13A Man for All Seasons

    A Man for All Seasons (1966)

    ★ 7.3/10Also drama

    A depiction of the conflict between King Henry VIII of England and his Lord Chancellor, Sir Thomas More, who refuses to swear the Oath of Supremacy declaring Henry Supreme Head of the Church in England.

  14. 14Oliver!

    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…

  15. 15Newsies

    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…

  16. 16Peterloo

    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…

  17. 17Blue 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…

  18. 18God's Not Dead 2

    God's Not Dead 2 (2016)

    ★ 6.2/10Also drama

    When a high school teacher is asked a question in class about Jesus, her reasoned response lands her in deep trouble and could expel God from the public square once and for all.

  19. 19Denial

    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.

  20. 20The Pelican Brief

    The Pelican Brief (1993)

    ★ 6.6/10Also drama

    A law student's theory about the recent deaths of two Supreme Court justices embroils her in a far-reaching web of murder, corruption, and greed.

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