Skip to content

Movies like Milton Jones: Milton Impossible (2023)

The best movies like Milton Jones: Milton Impossible (2023) are Held Up (1999), The Happiest Days of Your Life (1950) and Thunderstruck (2012). If Milton Jones: Milton Impossible hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. 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

  2. The Happiest Days of Your Life (1950)

    Nutbourne College, an old established, all-boys, boarding school is told that another school is to be billeted with due to wartime restrictions. The shock is that it's an all-girls school that has been sent. The two head teachers are soon battling for the upper hand with each other and the Ministry. But a crisis (or two) forces them to work together.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  3. Thunderstruck (2012)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  4. Adventures in Public School (2018)

    A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  5. Much Ado About Nothing (2013)

    A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  6. Fun with Dick and Jane (1977)

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

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  7. Sextuplets (2019)

    Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  8. Bill Burr: Drop Dead Years (2025)

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

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  9. 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
  10. Class Rank (2017)

    Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  11. Shane Gillis: Beautiful Dogs (2023)

    In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  12. Anuvahood (2011)

    Kenneth (who likes to call himself Kay) begins to realise he's just another wannabe bad boy... even less than a loser in fact. After quitting his job at Laimsbury's, Kay vows to become a respected gangster... or cry trying. A pulls-no-punches, coming-of-age story, centering on one directionless hopeless "shotter", who finds his true worth in the face of urban adversity.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  13. The Rutles: All You Need Is Cash (1978)

    The story of the rise and fall of the Pre-Fab Four.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  14. Clear History (2013)

    Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  15. Bill Burr: Walk Your Way Out (2017)

    No-nonsense comic Bill Burr takes the stage in Nashville and riffs on fast food, overpopulation, dictators and gorilla sign language.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. Moonwalkers (2015)

    What if Apollo 11 never actually made it? What if, in reality, Stanley Kubrick secretly shot the famous images of the moon landing in a studio, working for the US administration? This is the premise of a totally plausible conspiracy theory that takes us to swinging sixties London, where a stubborn CIA agent will never find Kubrick but is forced to team up with a lousy manager of a seedy rock band to develop the biggest con of all time.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  17. The TV Set (2007)

    As a writer named Mike struggles to shepherd his semi-autobiographical sitcom into development, his vision is slowly eroded by a domineering network executive named Lenny who favors trashy reality programming. The irony, of course, is that every crass suggestion Lenny makes improves the show's response from test audiences and brings the show a step closer to getting on the air.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  18. 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
  19. 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

    Popcorn FlickMovies like this
  20. Taylor Tomlinson: Have It All (2024)

    Can Taylor Tomlinson have it all? From dating woes to dream jobs to inventive dirty talk, she shares life's ups and downs in this stand-up comedy special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this

Like Milton Jones: Milton Impossible and something else?

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

Frequently asked questions

What are the best movies like Milton Jones: Milton Impossible?

The closest matches to Milton Jones: Milton Impossible are Held Up (1999), The Happiest Days of Your Life (1950) and Thunderstruck (2012). Below are 17 more, each with the reason it matches.

What should I watch after Milton Jones: Milton Impossible?

Start with Held Up (1999), the closest match to Milton Jones: Milton Impossible.

What is the highest-rated movie like Milton Jones: Milton Impossible?

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

What is the newest movie like Milton Jones: Milton Impossible?

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

Are there English movies like Milton Jones: Milton Impossible?

Yes: Held Up (1999), The Happiest Days of Your Life (1950) and Thunderstruck (2012).

How are movies similar to Milton Jones: Milton Impossible chosen?

First come films that Trakt’s viewers watch alongside Milton Jones: Milton Impossible, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

↑ ↓ to move · Enter to open · Full search page