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How Disney’s The Legend of Sleepy Hollow Tricks (and Treats) Us

Once Upon a Record

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For once you cross that bridge, my friends, the ghost is through, his power ends.

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Considered the first great American ghost story, Washington Irving's The Legend of Sleepy Hollow has been a staple of Halloween since the 19th century.

Disney might not have been the first to bring it to the big screen, but is there's still the best?

This is The Adventures of Ichabod (and Mr. Toad).

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Although I didn’t discuss them in my video, I have two Sleepy Hollow albums - one Disney, one not - as well as a Disneyland 45:

The Legend of Sleepy Hollow and Rip Van Winkle - Disneyland Records DQ-1285: The Legend of Sleepy Hollow and Rip Van Wi...
The Legend of Sleepy Hollow & Rip Van Winkle - Mr. Pickwick Records SPC-5156: The Legend of Sleepy Hollow & Rip Van Wink...
The Headless Horseman / Ichabod Crane - Disneyland Records LG-762: The Legend of Sleepy Hollow (LG-762) | Vin...
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You can find my complete series of Disney Deep Dive videos here:

Ep. 1 - The Music of Walt Disney: The Music of Walt Disney: More than just a...
Ep. 2 - Escape to Witch Mountain: Escape to Witch Mountain just keeps on giving
Ep. 3 - Country Bear Jamboree: The surprising legacy of Disney's Country ...
Ep. 4 - Snow White and the Seven Dwarfs: Snow White never got better than this
Ep. 5 - The Music of Fess Parker: How Fess Parker helped shape Disney's Wild...
Ep. 6 - Mary Poppins: Bringing Mary Poppins home for the first time
Ep. 7 - The Music of Soarin' over California: When Disney hired the perfect composer
Ep. 8 - The Shaggy Dog: It's time to rewatch Disney's original Sha...
Ep. 9 - The Music of The Hobbit (1977): The forgotten soundtrack of The Hobbit (1977)
Ep. 10 - The Tale of Disney's two Robin Hoods: When Disney Made the Same Robin Hood Movie...
Ep. 11 - The One and Only, Genuine Original Family Band: Why Doesn't Disney Want Us to Watch The On...
Ep. 12 - The Jungle Book: Disney’s Jungle Book Could Have Been Very ...
Ep. 13 - Peter Pan: The Mystery Hidden in Disney’s Peter Pan
Ep. 14 - The Gnome Mobile: The Gnome-Mobile is One Wild Ride
Ep. 15 - Pete's Dragon: We Should Probably Talk About Pete's Dragon
Ep. 16 - The Music of EPCOT Center: Why Epcot Center Felt So Unique
Ep. 17 - Lady and the Tramp: Lady and the Tramp Deserves More Credit
Ep. 18 - Bedknobs and Broomsticks: Bedknobs, broomsticks and Disney's Witchy ...
Ep. 19 - The Moon-Spinners: The Moon-Spinners Never Had a Chance
Ep. 20 - The Legend of Sleepy Hollow: How Disney’s The Legend of Sleepy Hollow T...
Ep. 21 - Tron: Video
Ep. 22 - Something Wicked This Way Comes: The Disney Halloween Movie You Forget to W...
Ep. 23 - Alice in Wonderland: Video
Ep. 24 - Mickey's Christmas Carol: Why We Always Come Back to Mickey’s Christ...
Ep. 25 - The Black Cauldron:
Ep. 26 - The Parent Trap: Video
Ep. 27 - The Love Bug: The Unrivaled Success of The Love Bug
Ep. 28 - The Apple Dumpling Gang: Disney's Most Unlikely 1970s Hit: The Appl...
Ep. 29 - The Rescuers: Disney Needed The Rescuers

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Chapters:
00:00 - Intros / Is Disney’s Sleepy Hollow still the best?
03:53 - Washington Irving
05:57 - Walt Disney and Bing Crosby
07:11 - Sleepy Hollow's main characters
08:34 - Halloween night
13:57 - The Package Era / Conclusions

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Be sure to check out my original YouTube channel - @disneyrecordlandwhere you will find my complete collection of restored children's albums.

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#AdventuresOfIchabod #LegendOfSleepyHollow #BingCrosby #DisneyPackageEra #DisneyVideoEssay

20 Comments

@GeoffBosco 1 year ago

My 5X great grandfather was the pastor of the Old Dutch Church when The Legend of Sleepy Hollow was published. He's mentioned in the story, but not by name: when the narrator tells us that Ichabod was second in learning in the entire village "only to the parson," He was talking about Thomas Gibson Smith who is buried five feet behind the church to this day.

@kelleyceccato7025 11 months ago

It always tickles me that Disney, known for sanding off the hard edges of the fairy tales it adapts, managed to give us the most book-accurate adaptation of Washington Irving's tale.

@kerplop 1 year ago

I watch “Ichabod and Mister Toad” every Halloween season. It’s so unique to the usual Disney formula.

@ttintagel 1 year ago (edited)

I know it's silly, but as a New Yorker I always feel a little swell of local pride whenever the Headless Horseman gets a mention. Your Draculas and your Frankensteins are great and all, but he's our homegrown monster!

@tknoff87 1 year ago

one thing that makes it great for me is watching Ichabod fight with his horse to get out of the valley really feels like one of those nightmares you get where you know you are in danger and trying to leave and you just can't move fast enough. It gives the scenes a great sense of tension between the silliness and that little bit of anxiety i get watching it because it trule feels like one of those nightmares

@ShanaReviews 11 months ago (edited)

small correction: Brom in the short isn't portrayed as a town bully, he's presented in narration as the town hero of sorts and is well liked by everyone, we even see he lets the animals part take in the spoils he brings back before Ichabod comes into town.

the only reason he's seen as a bully is because of his rivalry with Ichabod.

also, fun fact: Brom and Sleepy Hollow's art style played a vital role in inspiring the look of Beauty and the Beast, but also Brom's role in this short, inspired Gaston's role and the idea to have Gaston be presented as the town hero but go all in on making him the villain compared to Brom being the town hero.

@KevyNova 11 months ago

When Tim Burton’s Sleepy Hollow first came out, I was not happy that instead of a gangly looking schoolteacher, they made Ichabod a handsome police man. But then I went to see it out of curiosity and was thoroughly pleased with Burton’s unique twist on the story. Now I watch it every year.

@susanmacdonald4288 1 year ago

The explanation that the chase with the horseman is in Ichabod's head doesn't hold water, because Gunpowder is as terrified as he is.

@christopherwaldrop5293 1 year ago

I think of this as one of Disney's best films, period. Years later when I finally read Irving's original story I was impressed by how closely the adaptation followed it, keeping it short and straightforward and leaving just the right amount to our imagination.

@SequentiallyCompact 1 year ago

The Tim Burton Sleepy Hollow is a solid flick. No need to defend your taste in films with that one.

@Tigerlily.279.J 1 year ago

This film has been an October tradition for me since I was a kid. It’s so charming and whimsical, yet suspenseful and chilling. One of my favorites.

@tomowens7499 1 year ago

I have worked in the animation industry 37 years so far, worked at nearly every studio at one point or another on lots of great projects (and some duds)... Sleepy Hollow is to me the greatest cartoon ever made. it's gorgeous art, killer animation, great layouts (the vertical pan down to the roadway as Ichabod enters the hollow is a particularly good one) great music and lyrics... the film works on multiple levels, it's sophisticated enough that repeat viewings reveal more (as a kid I didn't grasp that Katrina is using Ichabod to make Brom jealous)... it is perfection

@RylanSmith-dc1pf 1 year ago

I’m a huge Bing Crosby fan and the legend of sleepy hollow is pretty much the only way modern audiences are introduced to him outside of Christmas music. For me, legend of sleepy hollow is so nostalgic and watching it is a Halloween tradition

@TomMSTie1138 1 year ago (edited)

I've watched this film practically ever Halloween my whole life, and it never really dawned on me before that none of the three characters are likable. It really gives the story a subtle nuance.

@deltonmcclary7341 1 year ago

Every October 1st, this bad boy is pulled out!!

@TheCommenterDragon 1 year ago

I freaking love the Disney adaptation of "The Legend of Sleepy Hollow", It's one of my all-time favorite incarnations of Washinton Irving's classic spooky tale! It certainly has good quality animation for a late 1940's film.

One of my favorite parts of the disney version, is when Ichabod is inside the hollow, and his paranoia starts making him hear animals talk, I mean the way the frog sounds when he croaks "Headless Horseman" always scared the crap out of me. And of course the Headless Horseman's laugh still lives rent free in my head to this day!

@bensalisbury6535 1 year ago

This and the Tim Burton one is a must watch every year for Halloween. Love this version such a classic.

@aaronwashington1973 11 months ago

I still remember seeing the cartoon on TV in the 70s and being terrified

I’m totally with you. Sleepy Hollow is the end. I’ll be all for me.

@hattree 1 year ago

This film was owned in 16mm by my school district, and I saw it at least once every Halloween for 8 years in grade school. The songs from this live in my head.

@englishpro.laboulaye691 11 months ago (edited)

I am fascinanted by this film . I saw it as a child and I have watched it I can't tell how many times. I have been using it in my English classes for the last 6 years, and I never get tired of it. Most of my students have not seen it before, and they get as delighted as I do.