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Movies Like The Great Gildersleeve

If you liked The Great Gildersleeve (1942), a comedy movie directed by Gordon Douglas, 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. 1Fun with Dick and Jane

    Fun with Dick and Jane (1977)

    ★ 6.6/10Also comedy

    When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.

  2. 2Little Big League

    Little Big League (1994)

    ★ 6/10Also comedy

    When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take…

  3. 3Rookie of the Year

    Rookie of the Year (1993)

    ★ 6.2/10Also comedy

    When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.

  4. 4Thunderstruck

    Thunderstruck (2012)

    ★ 6.2/10Also comedy

    After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.

  5. 5Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry

    Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)

    ★ 7.1/10Also comedy

    Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.

  6. 6John Mulaney: Kid Gorgeous at Radio City

    John Mulaney: Kid Gorgeous at Radio City (2018)

    ★ 7.9/10Also comedy

    John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.

  7. 7Easy Money

    Easy Money (1983)

    ★ 6/10Also comedy

    To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.

  8. 8Stewie Griffin: The Untold Story

    Stewie Griffin: The Untold Story (2005)

    ★ 6.9/10Also comedy

    The maniacal baby of the Griffin family, Stewie, meets his future self. In doing this he discovers that his future image is not what he has anticipated because of a near death experience.

  9. 9Playing with Fire

    Playing with Fire (2019)

    ★ 6.6/10Also comedy

    A crew of rugged firefighters meet their match when attempting to rescue three rambunctious kids.

  10. 10Chris Rock: Never Scared

    Chris Rock: Never Scared (2004)

    ★ 7.5/10Also comedy

    Chris Rock, the three-time Emmy Award-winner, comedian, actor, and host of HBO's acclaimed The Chris Show, stars in his fourth solo stand-up special for HBO, Chris Rock: Never Scared. Featuring his unique, insightful…

  11. 11The Wedding Year

    The Wedding Year (2019)

    ★ 5.9/10Also comedy

    A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.

  12. 12Fist Fight

    Fist Fight (2017)

    ★ 6/10Also comedy

    When one school teacher gets the other fired, he is challenged to an after-school fight.

  13. 13Adam Sandler: Love You

    Adam Sandler: Love You (2024)

    ★ 6.3/10Also comedy

    Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.

  14. 14Bill Burr: Drop Dead Years

    Bill Burr: Drop Dead Years (2025)

    ★ 7.2/10Also comedy

    In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.

  15. 15Monkey Business

    Monkey Business (1952)

    ★ 6.7/10Also comedy

    Research chemist Barnaby Fulton works on a fountain of youth pill for a chemical company. One of the labs chimps gets loose in the laboratory and mixes chemicals, but then pours the mix into the water cooler. When…

  16. 16The Three Stooges

    The Three Stooges (2012)

    ★ 5.8/10Also comedy

    Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the…

  17. 17The Hangover Part III

    The Hangover Part III (2013)

    ★ 6.2/10Also comedy

    This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off.

  18. 18Jackass Presents: Bad Grandpa

    Jackass Presents: Bad Grandpa (2013)

    ★ 6.2/10Also comedy

    86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.

  19. 19The Distinguished Gentleman

    The Distinguished Gentleman (1992)

    ★ 6/10Also comedy

    A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows…

  20. 20Dave Chappelle: The Unstoppable...

    Dave Chappelle: The Unstoppable... (2025)

    ★ 6.7/10Also comedy

    Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.

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