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Home»Entertainment
Entertainment

4 Weirdest Children’s Movies of All Time, Ranked: ‘Labyrinth’ and More

June 7, 20265 Mins Read
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The summer of 2026 began with a baffling animated adaptation of the classic English class novel Animal Farm, George Orwell‘s critique of totalitarianism.

Why distributor Angel Studios thought today’s children would be interested in a creepy-looking CGI animal movie about proletariat rebellion is a true mystery (they could just watch Chicken Run, after all), and across-the-board negative reviews quickly put that sickly Animal to sleep.

One positive result from that film’s disastrous release is that it got Watch With Us thinking about some of the weirdest children’s movies of all time.

From a deranged Wizard of Oz sequel to a Jim Henson classic, we ranked the top weirdest children’s movies of all time.

4. ‘Son of the Mask’ (2005)

When family man and aspiring cartoonist Tim Avery (Jamie Kennedy) finds a mysterious mask delivered by his dog, Otis, he dons the mask at a Halloween party and finds himself developing strange powers. Meanwhile, his pregnant wife, Tonya (Traylor Howard), gives birth to a baby who is imbued with the powers of the mask. Together, dog and baby use the mask to create chaos for Tim and Tonya, who try to contain the damage being wrought. At the same time, the mask’s owner, Norse god Loki (Alan Cumming), seeks to get his artifact back, but only ends up causing more problems.

Those who were children in 2005 distinctly remember seeing TV ads for Son of the Mask and feeling deeply unsettled, despite the fact that the movie is billed as a family-friendly sequel to the Jim Carrey movie The Mask from 1994. What results is a catastrophe in just about every aspect, and one which effectively ended Kennedy’s acting career after giving him the unfair expectation of following Carrey’s performance. Cacophonous, unfunny and creepy in the worst ways, Son of the Mask is unforgettable in all the wrong ways.

3. ‘Chitty Chitty Bang Bang’ (1968)

At the request of his two young children, Jemima (Heather Ripley) and Jeremy (Adrian Hall), eccentric inventor Caractacus Potts (Dick Van Dyke) sets out to restore a broken-down race car and rename it Chitty Chitty Bang Bang. During their first trip in the car — accompanied by candy company heiress Truly Scrumptious (Sally Ann Howes) — Caractacus tells Jeremy and Jemima a fantastical story in which Chitty has magical powers, and is instrumental in battling a kid-hating Baron (Gert Fröbe) and his henchman known as the Child Catcher (Robert Helpmann).

If your parents showed you Chitty Chitty Bang Bang when you were a kid, it’s likely that you probably don’t remember the somewhat intricate plot, because you were too busy being traumatized by the Child Catcher. Helpmann’s performance as the Child Catcher is iconic, but it’s almost too good. While the movie features some unforgettable songs and a great performance by the always delightful Van Dyke, Chitty Chitty Bang Bang is largely looked back on with fear by grown-up kids for the terrifying Child Catcher and his giant net.

2. ‘Labyrinth’ (1986)

In a moment of frustration, young Sarah (Jennifer Connelly) wishes that her baby half-brother Toby (Toby Froud) would be whisked away by the goblins from her book, The Labyrinth. But what Sarah doesn’t realize is that her wish carries very real consequences, and thus Toby really does disappear. The Goblin King Jareth (David Bowie) appears before Sarah, informing her that she has thirteen hours to solve his labyrinth or her little brother will be turned into a goblin forever. After Sarah accepts Jareth’s quest, she finds herself on a fantastical journey in which she meets various strange, helpful and malevolent creatures.

Labyrinth is a terrific film, but it’s also a very unnerving one, and kids’ movies that are good but also scary are necessary in building character. Directed by none other than Jim Henson and filled with creations from his Creature Shop, Labyrinth might be a little spooky and unsettling at times, but it’s a childhood classic for many who grew up with it; an enchanting, unique fantasy with gorgeous special effects and an antagonist performance that feels tailor-made for Bowie.

1. ‘Return to Oz’ (1985)

This unofficial sequel to the 1939 Wizard of Oz classic combines elements of multiple Frank L. Baum novels to create a disturbing dark fantasy film. Return to Oz follows Dorothy Gale (Fairuza Balk) in the aftermath of her journey to Oz, and her insistence on having gone there troubles her Aunt Em (Piper Laurie) and Uncle Henry (Matt Clark). So, what do they do? They bring poor Dorothy to a sanatorium. Dorothy quickly escapes and is transported back to Oz, but it’s not all songs and sunshine anymore. The Yellow Brick Road is reduced to rubble, and the Emerald City is in ruins. It’s up to Dorothy to save Oz and her friends, who have been turned to stone.

Return to Oz might actually be too creepy for a kids’ movie, with some genuinely terrifying imagery courtesy of its dark narrative and the characterization of a creature known as the “Wheelers.” But while Return to Oz was a bit too weird to receive a rosy place in people’s childhood memories, it has gained an adult cult following. In particular, fans of the Oz books view it as a more faithful interpretation, but ultimately, Return to Oz is an incredibly unique film overall, with technical craft and filmmaking flair that finds greater appreciation in mature audiences.

Read the full article here

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