7 Things You Didn’t Know About the Legend of Sleepy Hollow

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There’s More to This Classic Disney Film Than You Realized

To get in the Halloween Spirit, we decided to rent the classic 1949 Disney cartoon, The “Legend of Sleepy Hollow” – and it was nothing like we remembered.

If it’s been years since you watched the cartoon, you may be in for a few surprises as an adult viewer. Here are some things we discovered watching the cartoon as adults.


You Can’t Just Rent it on Its Own

The Legend of Sleepy Hollow is actually the second half of a film called “The Adventures of Ichabod and Mr.Toad.” You can rent the film through the Disney Movies Anywhere App or Amazon.com.


Celebrity Narration

Bing Crosby provided the narration and voices for the film’s main characters. Famous for his warm voice, and Christmas albums, Crosby recorded “The Legend of Sleepy Hollow” during the height of his film and singing career.


Beauty and The Beast Similarities

Pay close attention to the opening scene of the animated film. Ichabod Crane walks through the streets of his small town with his nose stuck in a book, just like Belle does during the opening scene of “Beauty and the Beast.” Both characters are described as peculiar by the towns people, and it’s acknowledged that they don’t quite fit in. If Brom Bones seems familiar to you it’s probably because he bares a striking resemblance to Gaston. Both characters are seen as bullies, in desperate pursuit of the prettiest girl in town.


Katrina Bares a Resemblance to Another Disney Character

Disney characters often bare similarities to each other. For example, Alice from “Alice in Wonderland” has the same face as Wendy from “Peter Pan.” Disney’s famous Nine Old Men worked on both films, and both films starred Kathryn Beaumont. In “The Legend of Sleepy Hollow,” Katrina Van Tassel bares a striking resemblance to Cinderella. It was just one year after “The Legend of Sleepy Hollow” was released that Disney debuted the animated classic “Cinderella,” so its safe to say animators were working on both at the same time.


Ichabod Crane is NOT a Good Guy

You might remember Ichabod Crane as the protagonist of the film. He’s intelligent, charming and confident – despite being bullied daily by Brom Bones and his crew. What you might not remember about Ichabod Crane is his womanizing ways. He prays on the single and widowed women of the town, charming them with his wit and dreamy voice to secure free meals. Ichabod’s always hungry, and it appears as though there’s no shortage of women ready to feed his insatiable appetite.

When Ichabod meets town beauty, Katrina Van Tassel, he’s enamored by more than just her beauty. Ichabod fantasizes about marrying rich, and taking over Katrina’s father’s fortune upon his death. If the fact that he’s a gold digger wasn’t bad enough, he’s also a horrible teacher. He’s too busy dreaming up ways to creep on Katrina to teach his class of impressionable children.


The Headless Horseman Barely Appears in the Film

While the story of Sleepy Hollow is supposed to be all about the Headless Horseman, he plays a very small part in the film. It’s not until the very end of the film that Ichabod meets the Horseman in the graveyard on his way home from the Van Tassel’s. Their exchange is swift, and the film is over before you can comprehend why you thought this movie was so scary as a kid.


There’s No Clear Ending

The narrator provides viewers with a dual ending. We see the Headless Horseman chuck his Jack-o-Lantern head at Ichabod, and then the screen goes black. The narrator tells us Ichabod was never heard from again. The audience is left with a choice, to believe the rumors that Ichabod married a widow in a neighboring town – or that his soul was spirited away on Halloween Night by the Headless Horseman.

Moral of the story, things you remember watching as a kid may hold a completely different meaning to you as an adult.

Michelle McKinley is a journalist and digital marketer from Los Angeles, CA. She earned her Journalism degree from Pepperdine University, and has been writing for the web since 2003. She’s a life-long Disney fan who travels and writes about her experiences for fun.

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