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Movies like Gary's War (2008)

The best movies like Gary's War (2008) are The Roast of Tom Brady (2024), Dave Chappelle: The Unstoppable... (2025) and Held Up (1999). If Gary's War hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. The Roast of Tom Brady (2024)

    Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.

    Why it matches: Recommended by TMDB viewers · both comedy

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  2. Dave Chappelle: The Unstoppable... (2025)

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

    Why it matches: Recommended by TMDB viewers · both comedy

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  3. Held Up (1999)

    What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.

    Why it matches: Recommended by TMDB viewers · both comedy

  4. Iliza Shlesinger: War Paint (2013)

    Her innocent appearance is just a cover for Last Comic Standing winner Iliza Shlesinger's acerbic, stream-of-conscious comedy that she unleashes on an unsuspecting audience in her hometown of Dallas in "War Paint," her first stand-up special.

    Why it matches: Recommended by TMDB viewers · both comedy

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  5. Eric Andre: Legalize Everything (2020)

    Comedian Eric Andre presents his very first Netflix original stand-up special. Taking the stage in New Orleans, Andre breaks the boundaries of comedy as he critiques the war on drugs, the war on sex, and the war on fart jokes!

    Why it matches: Recommended by TMDB viewers · both comedy

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  6. Jimmy Carr: His Dark Material (2021)

    Jimmy Carr finds humor in the darkest of places in this stand-up special that features his dry, sardonic wit — and some jokes he calls "career enders."

    Why it matches: Recommended by TMDB viewers · both comedy

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  7. Kelly's Heroes (1970)

    A misfit group of World War II American soldiers goes AWOL to rob a bank behind German lines.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  8. No Time for Sergeants (1958)

    Georgia farm boy Will Stockdale is about to bust with pride. He’s been drafted. Will’s ready. But is Uncle Sam ready for Will?

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  9. Ricky Gervais: Armageddon (2023)

    Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  10. Ali G, Innit (1999)

    Ali G travels throughout Britain, interviewing unsuspecting leaders and politicians.

    Why it matches: Recommended by TMDB viewers · both comedy

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  11. Malibu Rescue: The Next Wave (2020)

    It’s summer again, and everyone’s favorite Junior Rescuers, The Flounders, are back at Tower 2. With the International Junior Rescue Championships headed to Southern California, the eyes of the entire planet are on Malibu Beach. But when Team USA falls victim to a bout of food poisoning, it’s up to Tyler, Dylan, Eric, Lizzie and Gina to represent their country in the world's most extreme lifeguard challenge!

    Why it matches: Recommended by TMDB viewers · both comedy

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  12. Cadet Kelly (2002)

    Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.

    Why it matches: Recommended by TMDB viewers · both comedy

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  13. Me Time (2022)

    With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.

    Why it matches: Recommended by TMDB viewers · both comedy

  14. Ricky Gervais: Mortality (2025)

    Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  15. Ricky Gervais: Humanity (2018)

    In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  16. Chris Rock: Never Scared (2004)

    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, and hilarious views on a host of social, political and, celebrity issues, Rock confirms his stature as the leading comic of our time.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  17. Adam Sandler: Love You (2024)

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

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  18. Jimmy Carr: Natural Born Killer (2024)

    Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. Dave Chappelle: The Dreamer (2023)

    From his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  20. Playing with Fire (2019)

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

    Why it matches: Recommended by TMDB viewers · both comedy

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Like Gary's War and something else?

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

Frequently asked questions

What are the best movies like Gary's War?

The closest matches to Gary's War are The Roast of Tom Brady (2024), Dave Chappelle: The Unstoppable... (2025) and Held Up (1999). Below are 17 more, each with the reason it matches.

What should I watch after Gary's War?

Start with The Roast of Tom Brady (2024), the closest match to Gary's War.

What is the highest-rated movie like Gary's War?

Ricky Gervais: Humanity (2018), rated 7.6/10 by 547 TMDB users.

What is the newest movie like Gary's War?

Ricky Gervais: Mortality (2025) is the most recent release on this list.

Are there English movies like Gary's War?

Yes: The Roast of Tom Brady (2024), Dave Chappelle: The Unstoppable... (2025) and Held Up (1999).

How are movies similar to Gary's War chosen?

First come films that Trakt’s viewers watch alongside Gary's War, 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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