March 2, 2024

Gabbing Geek

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Jenny’s 31 Days of Halloween! – The Legend Of Sleepy Hollow

"With a hip-hip and a clippity-clop He's out lookin' for a top to chop So don't stop to figure out a plan You can't reason with a headless man!"

Welcome to my 31 Days of Halloween! Each day in October I will be watching a Halloween(ish) movie which includes anything that helps get me into the spooktacular mood of the season. While watching each movie, I’ll record my inner ramblings for everyone to view. This is a true baring of my soul people! Just kidding, it’s not – but it will be a true honest-to-god reaction to everything I’m seeing. So if “inner monologue” articles are not your thing – maybe you pass this up. For those of you sticking with me, the genre I’ll be watching will revolve around Halloween themes, including (but not limited to): Thrillers, Horror, Suspense, and of course Disney Classics! So buckle up campers, it’s going to be a bumpy ride!



Man do I love Disney’s: The Legend of Sleepy Hollow – the retelling of Washington Irving’s story set in a tiny New England town.  

When my brothers and I were kids, and before 31 Days of Halloween on ABC Family/Freeform (whatever you want to call it), my mother had a line up of Halloween movies ready at the waiting. You see, my mom was a teacher, and if there was anything she knew how to do, it was keep kids busy. 

During the Halloween season, Disney cartoons were a staple in our house. And – throughout the years, there was no shortage of them. And – when we get closer to Halloween itself, I’ll be reviewing a TV Special called “Disney’s Halloween Treat,” which is a collection of all the Disney Halloween cartoons, but like I said, I’ll do that another day. 

What I love about this story is that, for one, it’s narrated by Bing Crosby. Every descriptive adjective about Ichabod Crane is delicately sung by one of the best crooners of all time. And, in my humble opinion dear old Ichabod Crane is of the most underutilized characters in Disney’s line-up. Ichabod reminds me of what Scrooge would/should have looked like when he was young, only kinder – but I digress. 

What’s beautiful and wonderful about this little cartoon is that all the spooky storytelling is done through song and sounds. The art plays on our anxiety of haunted images, while the whistles in the background raise the hair on the back of our necks. It’s so simple, yet so brilliantly done. And the lanky and emotive Ichabod is the perfect subject to visualize our own fears if we too were riding through the woods at midnight on Halloween .

So, when the star of the show: The Headless Horseman, finally shows up – we’re already primed for a full-blown nightmare meltdown. And Disney doesn’t hold back. The Horseman is essentially a faceless demon villain – but between his maniacal laugh, and ruthless goal to chop some heads, he’s one of the best villains in the Disney Vault. I think the song from the ending of the movie sums him up perfectly: 

“With a hip-hip and a clippity-clop
He’s out lookin’ for a top to chop
So don’t stop to figure out a plan
You can’t reason with a headless man!”

There is definitely no reasoning with a headless man. 

Anyway – I love the charm and creativity of this little vignette – and if you get a chance to watch it this season, I hope you’re filled with the same kind of Halloween nostalgia that is only worthy of a cartoon seen again through your younger, more innocent self.