Disney Dynasty – The Legend of Sleepy Hollow

By Joshie Jaxon 

Greetings, geek fans! A new Halloween post is here. I’ve loved this one since I was kids, though admittedly, part of it scared the bejeezus out of me. As a kid it was scary imagery, as an adult it’s putting myself in that situation. More on that as the show progresses. Let the geeks begin! 

Our story begins in colonial New York, a short distance from Manhattan, in a place called, say it with me now, Sleepy Hollow. It’s a quiet, quaint little down, but it’s also foreboding. It is full of twilight tales, and local superstitions. Hey, they didn’t have internet, they needed to entertain themselves. Incidentally, the story is narrated by none of than Bing Crosby. I tell you this so when I say that Bing said, you don’t think I’m using the internet. Besides, he’s got such a pleasant voice. Bing tells us that there’s a tale of a local schoolmaster who once frequented the area. A pedagogue described as a most unusual man, one might mistake for a scarecrow. Tall, lank, small head, flat on top, with a long, snipe nose. As if a weathercock were perched on his spindle neck. We get it, he’s thin. It’s colonial times. Girl needs a sammich. 

One drowsy afternoon, at the old Snooker & Schnapps Shoppe, the rustic Sleepy Hollow Boys were gathered. Their leader, Brom Bones arrives, with a “yahoo”. Bing tells us he’s a burly, roistering blade, always ready to fight or frolic. I just bet he is. He’s a prankster, but there’s no malice to them. He’s loved in the whole county. He then opens a keg, pours a round for the guys, the breaks open the lid so that his horse and the local dogs can drink too. Yes, this is still Disney. It’s the 40’s, be glad that it isn’t historically worse. As the guys finish their drinks, Brom sees Ichabod through the bottom of his glass. He says “odd bodkin! Gadzooks!” It’s so quaint, I love it. 

Time for a musical number. The library is open. “Who’s that coming, down the street? Are they shovels or are they feet? Lean and lanky. Skin and bones. With clothes a scarecrow would hate to own. Yet, he has a certain air. Debonair and devil may care. It’s the new schoolmaster, what’s his name? Ichabod. Ichabod Crane.” During this song, Ichabod is sauntering through town with his nose in a book. He managers to avoid walking under a ladder, and also turns around a black cat that attempts to cross his path. Remember that, people. It’s a character point. As he continues, he opens a gate for a woman with a tray of pies. One appears in his book, and he scarfs it down. Told ya, girl is hungry. The townspeople all agreed they’d never seen anyone like Ichabod Crane. 

The school became Ichabod’s empire. With lordly dignity, he held absolute sway. We see him peeking in kids’ lunch baskets as they’re doing their work. He sees two boys drawing a picture on their slate of him as a bird. Bing tells us that Ichabod believes in the golden maxim, “spare the rod, spoil the child”. As we see him wind up to take a swing, yes really, he notices the heaping lunch the kid has, and decides to discriminate. It’s better to stay on good terms with the kids, especially if their moms could cook. Cut to Ichabod at a student’s house, sniffing the fresh turkey that the mother just finished cooking. Are we sensing a pattern?

Ichabod is in bed writing in his food journal, again, yes, seriously, as Bing sings. Who’s the town’s ladies man? Gets around like nobody can. I dunno if he’s putting out for these moms, or just charming them for food. I’d like to think he’s a man whore. After all, you know what they say about tall, thin, guys; they have big… Appetites. We’re also told that he has creative ways of padding his limited income. *cough hooker! *cough. By means of introducing culture to the town, as their choir director. We hear the ladies sing in harmony as Ichabod “boms” some notes at them. They’re all seduced and practically swooning. Dunno if that’s in the book, or just an excuse for Crosby, either way, it’s fun. As he’s finishing, Brom is outside, and gets a dog to howl on the final note. Ichabod thinks it came from himself, but the ladies are too wet to care. They all hit the ground, captivated. Bing tells us it was only natural that Ichabod be the ridicule of Brom and his gang, but despite that, he maintained an even temperament. Rather than indulging in the ladies, he instead takes advantage of the salad on the table. He doesn’t even toss it. Not a single leaf. 

Then there was the fateful day when SHE came to town. Katrina Van Tassel. Side note, I had a teacher in middle school who claimed to be her descendant, but given how the rest of the story goes, that wouldn’t have been her last name, and therefore wouldn’t have been his. Katrina was the daughter of the richest farmer in the county. Bing describes her as a blooming lass, plump as a partridge. Ripe, melting, and rosy-cheeked. Um, that’s a little much, Bing. Town it down. He sings of her being a coquette, as we see her charm all the local men into unloading her cart, setting up a picnic, then moving it to a better location when she objects to the first. That’s kinda diva, but not in the fierce way. That’s just taking advantage. Bing confirms it by saying she’ll kiss and run, to her, a romance is fun. There’s always another to start. Tease! Ichabod is on a date, but sees Katrina and is dumbstruck. He sits on the cake, puts the chicken on his head, and starts eating his hat. Look, I know the pickins had to be slim, but she can’t be that great, can she? 

Schoolhouse, kids running wild. Book propped up at the head of the class with the beatin’ stick, er, pointer. Ichabod is busy daydreaming. Katrina, would could resist your charm. Who could resist your father’s farm? Gold in those acres, and that ain’t hay. Oh, Katrina my treasure. Treasure. That barn is a gold mine. He’d love to hit the jackpot. Alright, this is definition of gold-digger. He even goes so far as to think that daddy can’t take it with him, and once he dies, Ichabod will step in. Poor little rich girl. Ichabod will protect you. Men are pigs. Only wants her for her looks and her money. I get it, you don’t want to teach forever, but c’mon. Seriously, grow a pair and take care of yourself. 

In town, Katrina is shopping, and handing her purchases to one of the various men that are smitten with her. I’d like to point out that in To Wong Foo, a group of guys were ready to gang bang Miss Chi Chi on day one, yet these ones, despite outnumbering her, are content to carry her stuff. Yes, Disney universe vs our own, I get it. However, given that she knows what she’s doing, and Ichabod’s fantasy proves he doesn’t care about her at all as a person, the whole thing is just stupid. For the record, I don’t condone “rape culture”. I’m not saying she’s asking for it. Are we clear? Good. Ichabod seems to think brains will give him an advantage in the dating pool over the bumpkin locals. What he didn’t count on was Brom clearing them all away. Bing says it piqued and provoked Katrina. Ichabod shows up and picks up all the packages the other men had left when Brom made them leave. Katrina gives some good side-eye to Brom, then smiles at Ichabod. He begins to walk her home, but stops at a small stream in town, and takes off his coat so she can step on it and not ruin her shoes. Side bar, if she’s using him, and he’s more than willing to be used, are they still both bad people, or does that make them a perfect match? Brom ain’t having it either way, and races on his horse through the muddy water, covering Ichabod, and somehow sparing Katrina. She’s on the back of Brom’s horse as he gathers her things. Not wanting her game over, she pulls a handkerchief from her bosom, and tosses it at Ichabod. He’s not giving up! 

In fact, Ichabod is so motivated, that he beats them to Katrina’s house, on foot. Who’d have thought the smell of colonial boob would be that great? Ichabod opens the gate, and offers Katrina his arm. She glances at Brom to make sure he’s seeing this, then leans in close before the walk on. Ichabod closes the gate, forcing Brom to fall over it, and drop all of her purchases. Uh oh, you don’t mess with a girl’s shopping. Ichabod and Katrina laugh, and the former stacks all the parcels back in Brom’s arms before escorting the lady inside. Brom scrambles after them, trips, and drops everything again. Ichabod goes out again to help pick things up. Brom is mad. The lower half of Katrina’s door is closed, so second base is the limit. Kidding. He kisses her hand and waves her off. As he turns to leave, Brom takes a swing at him. Ichabod goes inside, and closes the door. A lady, unescorted during the day? Scandal! He grabs flowers off the table and hands them to her while giving her goo goo eyes. She looks up and sees Brom trying to look inside the window above the door. Katrina places a flower in Ichabod’s lapel, and pulls him close. Brom wants in! Brom smash! Until he hears a kissing noise, and starts to go mad. It’s only Ichabod kissing a flower, but still. Ichabod leaves, and Brom grabs him by his ponytail. He’s all lined up to punch him, when Ichabod waves and we hear Katrina “yoo-hoo” from the window on the upper floor. Brom dusts him off, waiting for the curtains to close. When they do, he takes a blind swing, and punches a hole through a tree. Repeat, punches a hole through a tree! Cartoon or not, this is set in the real world, so damn! 


As the Van Tassel annual Halloween frolic drew near, Katrina decides to stoke the fires of the smoldering rivalry, by personally inviting Ichabod. We see him spiffing up in front of his mirror, and “splashing” himself with chalk dust. To this day, I don’t know why. It’s not fragrant and sure wouldn’t have been back then. Anyhow, he rides the horse he borrowed for the party, whistling the whole time. 

At the party, Ichabod feels he has the edge, and prides himself on his dancing. Brom sits to the side, feeling he’s been bested. As Ichabod is being charming and graceful, Brom notices a plump wallflower. She smiles at him, and he winces. Jerk. Big girls need love too. Brom then gets the idea to dump her on the schoolmaster. He offers her to dance; she grabs him and holds on for dear life. Cause after all, as we’ve learned from the past, women are nothing without men, so she isn’t about to give up her only chance at happiness. Yes, he hits me, but you just don’t understand! Sad to say there are still some out there with this mentality. Where was I? Oh yes, the dancing. The plump girl in green is laughing at having fun. Brom manages to get her with Ichabod, but he quickly trades back, and gets away from them. Brom chases after them. He tries to leave his dance partner on a bench, but she won’t go without a fight. He manages to lock her out of the room, and begins trying to get Ichabod to fall into the cellar. Doesn’t work on both counts. She busts in the lower half of the door, and goes right for Brom. I’d like to point out that for her height, there are several moments it looks like she’s giving him head. As LeVar Burton says, you don’t have to take my word for it. 

As the evening passed, Van Tassel asked his guests to tell ghostly tales of Halloween. Ichabod, busy loading up a plate, spilled the salt, and tossed some over his shoulder. Brom knew that Ichabod was a believer in spooks and goblins. This would be his moment. Gather round, and he’ll elucidate, on what goes on outside when it gets late. Round about midnight ghosts and banshees get together for their nightly jamboree. There’s things with horns and saucer eyes. Some with fangs about this size. During this, Ichabod is eating, and looking a tad nervous. Then the guests chime in. Some are fat, and some are thin. Some don’t even wear their skin! The window is blown open, the candles go out, and a girl screams. Ichabod wraps himself up in a curtain, as Brom sings. “When the spooks have a midnight jamboree, they break it up with fiendish glee. Ghosts are bad, but the one that’s cursed is the Headless Horseman, he’s the worst. When he goes a joggin’ across the land, holding his noggin in his hand, demons take one look and groan, and hit the road for parts unknown. Beware, take care, he rides alone! There’s no spook like a spook who’s spurned. They don’t like him, and he’s really burned. He swears to the longest day he’s dead, he’ll show them that he can get a head. They say he’s tired of his flaming top, he’s got a yen to make a swap. So he rides one night each year, to find a head in the hollow here. With a hip-hip, and a clippity-clop, he’s out looking for a head to swap. So don’t stop to figure out a plan, you can’t reason with a headless man.” During the whole tale, Ichabod looks like he’s gonna wet himself, and Katrina is super amused by it. Yeah, it’s just a story, but if you don’t know that, it’s pretty damn terrifying. Think about it, someone wants to cutoff your head and keep it as their own. It’s very Mombi. Brom says if they doubt his tale is so, he met the spook a year ago. He didn’t stop for a second look, but made for the bridge across the brook, cause once you cross that bridge my friends, the ghost is through his power ends. 

Later that night, as Ichabod rides home through the hollow, he’s filled with anxiety and terror, as the details of Brom’s story are in his mind. The clouds cover the moon, and the wind is making spooky noises. He tries to whistle his way through it, but as the crickets, frogs and toads are making noise, he can’t. He swears they’re croaking his name. He runs into what looks like a ghost, but it’s just a tree with two fireflies in it. Then the croaking almost sounds like “uh oh”. A crow/raven nearly collided with his face, cawing “beware”, as we see the cemetery. Ichabod hears galloping, but his horse isn’t moving. He gets off, and tries to push it into going. When that doesn’t work, he ties pulling. He ends up falling backwards next to a log where cattails are beating against it, making the hoof noises. Ichabod laughs nervously as he discovers there was nothing to be afraid of. He even grabs some of them, and laughs maniacally, as he walks back to the horse. The horse gives himself over to laughing along with him. That is, until they hear the evil laughing of someone that isn’t them! They look over, and there’s the Headless Horseman! He pulls out a sword, and a flaming pumpkin from nowhere. Run, girl! 

The Horseman takes a swing, but Ichabod dodges it, and scrambles with the horse to get away. There’s nearly two minutes of the Horseman taking swings at Ichabod as he tries to escape. It doesn’t sound like a lot, but when you’re watching it and invested, you’re right there with him. There’s no streetlights, no cops, not a lot of people in the “new world”. It’s just you, and someone without a head, on a horse, with a sword, trying to kill you. That shit’s scary. Here’s the worst part of it, as a kid I thought, oh it’s just Brom trying to scare him, but he produces the pumpkin from nowhere, and it taking swings not just at Ichabod, but at the horse. Bing established earlier that there’s never been malice in Brom’s pranks before, which leads me to believe that in this particular cartoon universe, the Headless Horseman is real. Further evidence of this, is that when Ichabod finally makes it through the bridge, the Horseman stops. If that’s Brom, he wouldn’t feel the need to honor that part of the legend. Even though he stops at the bridge, and Ichabod makes it to the other side, the Horseman throws the flaming pumpkin at him. Ichabod had been looking back, and was paralyzed with fear, the inference is that the pumpkin hits him in the head. Now, if the Horseman can’t cross the bridge, how would the pumpkin be able to? These are the things I think about. For that matter, the Horseman just wants head. I’m sure Ichabod could have managed to give him some to keep himself alive. Hell, in a life or death situation, I’d offer it up. Gotta go with your strengths.

The next morning, Ichabod’s hat is found, and so are the remains of a pumpkin. No trace of the schoolmaster. Can’t cross the bridge. How would he have gotten rid of Ichabod? Cut to a short time in the future where Brom and Katrina are married. Bing tells us there were rumors of Ichabod still being alive, and married to a widow in another county, but the people of Sleepy Hollow wouldn’t believe it. They knew he was spirited away by the Headless Horseman. *Bing mic drop

There you have it, ladies and gents. Another glorious Halloween tale. I got another today from the stop-motion animation era. I’ve never seen it. I don’t know how good or bad it’ll be, as it’s from 1967, but I’m working on it for you. Until next time, stay geeky, and keep gabbing! 

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