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Movies like On the lollipop…

The best movies like On the lollipop… are Much Ado About Nothing (2013), Fun with Dick and Jane (1977) and The Roast of Tom Brady (2024). If On the lollipop… hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. 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
  2. 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
  3. 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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  4. Sea Scouts (1939)

    Donald is an admiral on a seagoing voyage with his nephews in which they encounter a ravenous shark.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  5. Accident Man (2018)

    Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.

    Why it matches: Recommended by TMDB viewers · both comedy

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  6. 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
  7. Wake Up, Ron Burgundy: The Lost Movie (2004)

    While Ron Burgundy's rivalry with Veronica Corningstone escalates quickly, a group of unprofessional thieves better known as 'The Alarm Clock' try to make the truth known, whatever that may mean...

    Why it matches: Recommended by TMDB viewers · both comedy

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  8. The Wedding Year (2019)

    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.

    Why it matches: Recommended by TMDB viewers · both comedy

  9. How to Irritate People (1969)

    A pre-Monty Python mockumentary, written by and presented by John Cleese, that provides tips on learning how to irritate people.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  10. 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
  11. A Knight for a Day (1946)

    By accident, Cedric (Goofy), replaces his master, Sir Loinsteak, in the armor just before the joust with champion Sir Cumference.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  12. The Errand Boy (1961)

    Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty ever finds is that he can cause havoc no matter what he does.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  13. Solid Serenade (1946)

    Tom ties up Spike and sneaks into the courtyard of the glamorous Toodles Galore with his bass, hoping to woo her with his song, much to the annoyance of a sleeping Jerry.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  14. Three O'Clock High (1987)

    Nerdy high schooler Jerry Mitchell is assigned to write an article for the school paper about the infamous new delinquent transfer student, Buddy Revell. When Jerry accidentally invades Buddy's personal space and touches him, Buddy challenges Jerry to an afterschool fight in the parking lot, which Jerry tries to avoid at all costs.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  15. His Mouse Friday (1951)

    Tom is shipwrecked on an island, which is inhabited by at least one mouse - Jerry. To thwart the hungry cat, Jerry disguises himself as a cannibal.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  16. Red Hot Riding Hood (1943)

    Tired of always playing the same roles, Little Red Riding Hood, her grandmother and the Wolf demand a new version of the tale. The story then plays out in a more contemporary urban environment, with Little Red Riding Hood working as a pin-up girl in a night club.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  17. How to Play Football (1944)

    Taking all the places on both teams, Goofy demonstrates the game of football with varying results, having problems with the coach and the goal post.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  18. Carry On Regardless (1961)

    After a bunch of no-hopers approaches an employment agency, the anarchy mounts as they do a series of odd jobs, including a chimp's tea party, trying to stay sober at a wine tasting… and demolishing a house.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. Puttin' on the Dog (1944)

    Jerry runs into a dog pound (and right on top of a napping Spike) to escape a rather mangy-looking Tom. To avoid being ripped to shreds, Tom borrows the head of a nearby dog statue. This easily fools the dogs, but not Jerry, and Tom keeps losing his newfound head...

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  20. Louis C.K.: Ridiculous (2026)

    From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  21. Chuck & Buck (2000)

    Chuck and Buck are childhood best friends whose lives have taken very different paths. While Chuck moved away and now has a real life, Buck stayed behind and developed a dangerous fixation—on Chuck's life.

    Why it matches: Similar story and style · both comedy

    Popcorn FlickMovies like this
  22. Sucker (2022)

    A troubled young man is taunted by a lollipop.

    Why it matches: Similar story and style · both comedy

  23. Earl and the Magic Lollipop (2022)

    A young man working at an empty bowling alley has a psychedelic nightmare when frequent bowler Earl offers him a magic lollipop.

    Why it matches: Similar story and style · both comedy

  24. Adventures of El Frenetico and Go Girl (1993)

    A drunken superhero and his kung-fu fighting girlfriend battle a local evil snack food king when he kidnaps a lady reporter.

    Why it matches: Similar story and style · both comedy

  25. Três Colegas de Batina (1961)

    The project of urbanization of a shantytown is endangered by lack of money. To get the necessary sum, three friars start to sing in plain clothes, incognito, also recording records and doing shows in nightclubs.

    Why it matches: Similar story and style · both comedy

  26. The Tenants (1987)

    A satirical comedy about the oddball inhabitants of a Tehran apartment building and their landlord.

    Why it matches: Similar story and style · both comedy

  27. Marriage Adventures (1959)

    Helena (Xenia Kalogeropoulou) returns to Greece after studying in Paris and on the ship home she meets Dinos (Dinos Iliopoulos). An attraction develops between them and after a while Dinos asks for her hand in marriage. Helena though cannot accept his proposal because she is pregnant.

    Why it matches: Similar story and style · both comedy

  28. The Big Fool (1967)

    Businessman Telis Birkas (Periklis Hristoforidis) decides to marry his daughter Antzela (Sasa Kastoura) with a nice guy, his accountant Dinos (Dinos Iliopoulos). Antzela though does not want to hear a word about it. Telis, decides to train Dinos in order for him to win his daughter's heart. Training does not go so well and so the call in the big guns.

    Why it matches: Similar story and style · both comedy

  29. Something Hot (1964)

    During an International Trade Fair at Thessaloniki, a mature woman, Rena (Martha Karagianni), goes there with her sister to convince her childhood friend Dinos (Dinos Iliopoulos) to have a "white wedding" so that she can inherit a large estate. Dinos though, does not accept because even though he is actually a womanizer he acts as a shy and modest man around people. Everyone there will meet a group of musicians and one of them will fall in love with the daughter of the strict manager of the company Dinos works for who is accompanied by Dinos. At some point, everyone goes to Athens where things get more complicated untill everyone finds his perfect match. In the end Rena gets her inheritance and all together they perform a musical play in a grand theater.

    Why it matches: Similar story and style · both comedy

  30. Every Cloud Has a Silver Lining (1958)

    Kostas (Dinos Iliopoulos), a small-time lawyer is tasked with accompanying Smaro (Smaroula Giouli), a young rich heiress, from the country to Athens where she wants to sell her estate. Kostas though starts a day late and Smaro goes to Athens by herself. In the end after much wandering and misunderstandings Kostas will meet Smaro who will fall in love with him.

    Why it matches: Similar story and style · both comedy

Like On the lollipop… and something else?

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

Frequently asked questions

What are the best movies like On the lollipop…?

The closest matches to On the lollipop… are Much Ado About Nothing (2013), Fun with Dick and Jane (1977) and The Roast of Tom Brady (2024). Below are 27 more, each with the reason it matches.

What should I watch after On the lollipop…?

Start with Much Ado About Nothing (2013), the closest match to On the lollipop….

What is the highest-rated movie like On the lollipop…?

Much Ado About Nothing (2013), rated 6.8/10 by 299 TMDB users.

What is the newest movie like On the lollipop…?

Louis C.K.: Ridiculous (2026) is the most recent release on this list.

Are there English movies like On the lollipop…?

Yes: Much Ado About Nothing (2013), Fun with Dick and Jane (1977) and The Roast of Tom Brady (2024).

How are movies similar to On the lollipop… chosen?

First come films that Trakt’s viewers watch alongside On the lollipop…, 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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