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Movies like The Creepy Pegman and The Upsidedown Woman (1993)

The best movies like The Creepy Pegman and The Upsidedown Woman (1993) are Chips Ahoy (1956), Beat the Devil (2002) and Naughty or Nice (2012). If The Creepy Pegman and The Upsidedown Woman hooked you with its fantasy, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Chips Ahoy (1956)

    Chip and Dale are starving in their tree home when they notice a plentiful supply of acorns on an island in a lake. To get to the island, they borrow a miniature model ship of Donald's to sail on. The irate Donald, however, doesn't appreciate them stealing his ship and makes several attempts to get it back and thwart their scheme to get to their acorn paradise. Chip and Dale are, of course, always one step ahead of Donald.

    Why it matches: Recommended by TMDB viewers · both fantasy

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  2. Beat the Devil (2002)

    The Driver drag-races the Devil, in order to earn James Brown his soul.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Worth the HypeMovies like this
  3. Naughty or Nice (2012)

    Krissy Kringle receives a delivery intended for Santa Claus. A magical book that shows if a person has been naughty or nice. She uses the book's power to find out about those around her, which leads to some very unusual and unintended results. Krissy realizes that everyone has some good and some not so good in them.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Popcorn FlickMovies like this
  4. Thru the Mirror (1936)

    Mickey has been reading Alice in Wonderland, and falls asleep. He finds himself on the other side of the mirror, where the furniture is alive.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Worth the HypeMovies like this
  5. Pirates of the Caribbean: Tales of the Code: Wedlocked (2011)

    Wenches Scarlett and Giselle fix each other up for their wedding, in which they would each marry their groom. Upon realizing that both their grooms were the same man, Jack Sparrow, the two wenches found themselves in an auction led by the Auctioneer. This short film serves as a prequel to The Curse of the Black Pearl, and explains just why Jack Sparrow's boat the Jolly Mon was seen sinking at the beginning of the whole story; why the wenches were so upset with him; and how Cotton lost his tongue.

    Why it matches: Recommended by TMDB viewers · both fantasy

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  6. The Fantastic Flying Books of Mr. Morris Lessmore (2012)

    After a hurricane levels his city, a young man wanders into a mysterious library where books literally come to life. This film won the Oscar for Best Animated Short Film in 2012.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Worth the HypeMovies like this
  7. Under the Sea: A Descendants Story (2018)

    Mal emerges from the shadows of a mystical forest onto a dark coastline where she crosses paths with Dizzy.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Worth the HypeMovies like this
  8. Kristin's Christmas Past (2013)

    Kristin, a cynical 34-year-old, drinks a mysterious champagne on Christmas Eve and wakes up seventeen years in the past, sharing a room with her 17-year-old self. Given the chance to change the worst Christmas of her life, she attempts to fix past mistakes, only to discover surprising truths about her family that may help her mend her present-day relationships.

    Why it matches: Recommended by TMDB viewers · both fantasy

  9. Borrowed Hearts (1997)

    Single mom Kathleen Russell (Roma Downey) and her daughter Zoey pretend to be Kathleen's boss's "family" so he can close a major business deal with the mysterious Mexican financier Javier Del Campo.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Popcorn FlickMovies like this
  10. Marvel One-Shot: All Hail the King (2014)

    A documentary filmmaker interviews the now-famous Trevor Slattery from behind bars.

    Why it matches: Recommended by TMDB viewers · both fantasy

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  11. Two of a Kind (1983)

    God has had enough of the bad behavior and attitude of humankind, and has decided to start it all over. It is up to a struggling inventor and a bank teller, both with very amateur criminal minds, to save the world by falling in love.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Popcorn FlickMovies like this
  12. Dr. Strange (1978)

    A psychiatrist becomes the new Sorcerer Supreme of the Earth in order to battle an evil Sorceress from the past.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Popcorn FlickMovies like this
  13. Destino (2003)

    Short film to a song of love lost and rediscovered, a woman sees and undergoes surreal transformations. Her lover's face melts off, she dons a dress from the shadow of a bell and becomes a dandelion, ants crawl out of a hand and become Frenchmen riding bicycles. Not to mention the turtles with faces on their backs that collide to form a ballerina, or the bizarre baseball game.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Worth the HypeMovies like this
  14. Do You Like to Read? (2012)

    The librarian of the town of New Penzance introduces six animated segments illustrating Suzy's favorite books.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Popcorn FlickMovies like this
  15. Lou (2017)

    A lost-and-found box holds a mysterious and unseen monster within.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Worth the HypeMovies like this
  16. DC Showcase: The Phantom Stranger (2020)

    Jess joins her friends at a party in a dilapidated mansion hosted by the mysterious Seth. When odd things begin to happen to Jess and her friends, the Phantom Stranger intervenes to save her from a dreary fate.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Popcorn FlickMovies like this
  17. The Willoughbys (2020)

    When the four Willoughby children are abandoned by their selfish parents, they must learn how to adapt their Old-Fashioned values to the contemporary world in order to create something new: The Modern Family.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Worth the HypeMovies like this
  18. Mythica: A Quest for Heroes (2014)

    Stuck in a life of indentured servitude, Marek dreams of becoming a wizard. When she meets the beautiful priestess Teela in need of help, she offers her assistance and provides a motley troupe. Together they go in search of Teela's sister, who was kidnapped by a wild ogre.

    Why it matches: Recommended by TMDB viewers · both fantasy

  19. DC Showcase: Death (2019)

    Vincent, an artist with unresolved inner demons, meets a mysterious girl who helps him come to terms with his creative legacy… and eventual death.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Absolute CinemaMovies like this
  20. Pinocchio (2009)

    The enchanted story of Pinocchio.

    Why it matches: Recommended by TMDB viewers · both fantasy

    Popcorn FlickMovies like this
  21. Indústrias Reunidas Machiavelli (2019)

    Agripino and Sandoval roam around their workplace, Machiavelli Incorporated, a venture which they plan to expand whatever the costs.

    Why it matches: Similar story and style · both fantasy

  22. Daydreaming So Vividly About Our Spanish Holidays (2022)

    Hungry for sun, light and warmth, a group of teenagers embark on a dream trip to the Balearic Islands.

    Why it matches: Similar story and style · both fantasy

  23. To Carry Underneath (2021)

    A harvester must safely carry her eggs across a difficult and threatening landscape.

    Why it matches: Similar story and style · both fantasy

  24. Narcose (2014)

    Deep water freediving exposes its practitioners to a form of narcosis, which induces several symptoms, among which a feeling of euphoria and levity that earned this phenomenon its nickname of "raptures of the deep". The short film relates the interior journey of Guillaume Néry, the apnea world champion, during one of his deep water dives. It draws its inspiration from his physical experience and the narrative of his hallucinations.

    Why it matches: Similar story and style · both fantasy

  25. Rain in the Sunshine (2013)

    Schoolboy Hinata has a big crush on his classmate Shigure, but is too shy to tell her. On the day Shigure is leaving, Hinata flies off on the wings of a bird chasing after her to tell how he feels!

    Why it matches: Similar story and style · both fantasy

  26. The Case of Patient Paul Edward Kelley (2015)

    A psychologist faces the case that will challenge his foolproof technique: the patient needs to forget something that he cannot remember. In this mental challenge, every step towards healing is a step beyond the edges of reason.

    Why it matches: Similar story and style · both fantasy

  27. OSARU-CHAN (2021)

    When two brothers steal a valuable heirloom from an elderly Japanese woman, they unknowingly awaken her demigod son, Osaru, who does not take kindly to thieves.

    Why it matches: Similar story and style · both fantasy

  28. The Myth of the Water Goddess (2022)

    A little girl will have to sing to the mythical goddess of water so that this valuable liquid can reach her community.

    Why it matches: Similar story and style · both fantasy

  29. The Graduation of Edison (2019)

    Minh lives in a village where every child is born with a tree on their heads, except for him. On graduation day, students who have turned 18 will get their tree cut to signify adulthood. Problems arise when Minh’s sister decides to keep hers.

    Why it matches: Similar story and style · both fantasy

  30. The Ugly Duckling (1968)

    A stop-motion puppet animation adaptation of Hans Christian Anderson's tale The Ugly Duckling.

    Why it matches: Similar story and style · both fantasy

Like The Creepy Pegman and The Upsidedown Woman and something else?

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Frequently asked questions

What are the best movies like The Creepy Pegman and The Upsidedown Woman?

The closest matches to The Creepy Pegman and The Upsidedown Woman are Chips Ahoy (1956), Beat the Devil (2002) and Naughty or Nice (2012). Below are 27 more, each with the reason it matches.

What should I watch after The Creepy Pegman and The Upsidedown Woman?

Start with Chips Ahoy (1956), the closest match to The Creepy Pegman and The Upsidedown Woman.

What is the highest-rated movie like The Creepy Pegman and The Upsidedown Woman?

Lou (2017), rated 7.5/10 by 441 TMDB users.

What is the newest movie like The Creepy Pegman and The Upsidedown Woman?

Daydreaming So Vividly About Our Spanish Holidays (2022) is the most recent release on this list.

How are movies similar to The Creepy Pegman and The Upsidedown Woman chosen?

First come films that Trakt’s viewers watch alongside The Creepy Pegman and The Upsidedown Woman, 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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