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Movies like Messing Around (1989)

The best movies like Messing Around (1989) are Fun with Dick and Jane (1977), Jim Jefferies: Freedumb (2016) and Driver's Ed (2026). If Messing Around hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. 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
  2. Jim Jefferies: Freedumb (2016)

    Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  3. Driver's Ed (2026)

    A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  4. Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)

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

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  5. 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
  6. John Mulaney: Kid Gorgeous at Radio City (2018)

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

    Why it matches: Recommended by TMDB viewers · both comedy

    Absolute CinemaMovies like this
  7. Mr. Bones (2001)

    A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  8. 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
  9. The Fixer Uppers (1935)

    Stan and Ollie are greeting card salesmen who agree to help a woman put a spark in her loveless marriage by making her husband jealous.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  10. Oliver the Eighth (1934)

    Barbershop owners Stan and Ollie answer an ad in the newspaper from a wealthy widow looking for a husband. Ollie only mails in his response and is invited to the widow's mansion. Stan discovers his unmailed letter and insists on tagging along. At the mansion, the widow's creepy butler informs them that the woman is crazy. She was once jilted by an Oliver and now her hobby is marrying Olivers and then slitting their throats. Now the boys must figure out how to escape.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  11. 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
  12. 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

  13. The Ladies Man (1961)

    After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with all these females?

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  14. 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
  15. Duplex (2003)

    When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. Trailer Park Boys: Don't Legalize It (2014)

    Out of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty deal. Meanwhile, Ricky’s dope growing business is under a major threat when the government announces a plan to legalize marijuana. Bubbles reluctantly joins them on his own quest to claim an inheritance left to him by his long-lost parents.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  17. 2 Minutes of Fame (2020)

    An up-and-coming stand-up comic moves to L.A. to pursue a film career after video clips of his act make him an online sensation.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  18. London Calling (2025)

    After fleeing the UK from a job gone wrong, a down on his luck hitman is forced to babysit the son of his new crime boss and show him how to become a man.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. Die, Mommie, Die! (2003)

    Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her husband. However, Angela's manipulative daughter, gay son and alcoholic maid are not going to make it easy for her.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  20. 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

Like Messing Around and something else?

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

Frequently asked questions

What are the best movies like Messing Around?

The closest matches to Messing Around are Fun with Dick and Jane (1977), Jim Jefferies: Freedumb (2016) and Driver's Ed (2026). Below are 17 more, each with the reason it matches.

What should I watch after Messing Around?

Start with Fun with Dick and Jane (1977), the closest match to Messing Around.

What is the highest-rated movie like Messing Around?

John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.

What is the newest movie like Messing Around?

Driver's Ed (2026) is the most recent release on this list.

Are there English movies like Messing Around?

Yes: Fun with Dick and Jane (1977), Jim Jefferies: Freedumb (2016) and Driver's Ed (2026).

How are movies similar to Messing Around chosen?

First come films that Trakt’s viewers watch alongside Messing Around, 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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