In a small village in New York, Ichabod Crane, stork-like itinerant school-master, woos the fair (and rich) Katrina Van Tassel with his charm, wit, erudition, and surprisingly competent dancing, much to the chagrin of his rival for her heart, Brom Bones. But Brom knows that Ichabod is a very superstitious fellow - a bit of a 'fraidy cat, really - so at a party for Katrina's father, Brom lays it on thick with a ghost story about a horseman who rides the nearby woods every Halloween night, looking to take a replacement for his missing head. Ichabod's fear of the story makes him lose face in front of his beloved Katrina, but he could lose a lot more when he meets the Horseman on his ride home.
This Disney animated short was a staple of my Halloweens growing up. It seems like every year this would come on TV and I would get myself nice and spooked by the real and imagined terrors of Ichabod's harrowing ride through the woods. The sky darkens, the woods seem to close in on him, voices seem to call out, "Ichabod..." and "Horseman..." And then the terrible phantom appears, riding a pitch black horse, cloak rippling in the wind, a long knife in one hand and a flaming Jack-o-Lantern in the other. Terrifying.
The first half of this cartoon is a bouncy, silly, cute romp with all the great animation that comes along with the Disney name. Ichabod, though a bit too scheming to be a fully noble protagonist, is a likable fellow, and it's fun to see him charming the ladies in town while in search of a good meal until he becomes smitten with Katrina. Then, amazingly, he bests his stronger, more attractive rival Brom at every turn, at least until the end.
I assume that this all pretty much jibes with Washington Irving's story (maybe I'll read it someday), so the credit can be given to the original author for subverting the trope of the put-upon underdog finally getting a chance to win the fair maiden's heart by using his wits to overcome his rival's strength. Here we have the opposite - despite being a creepy-looking, nebbish goof, Ichabod wins and wins and wins until Brom has a moment to find his one weakness and put him in his place. It's a great role-reversal.
(Wikipedia says that Katrina was only using Ichabod to make Brom jealous, but I never read that into the characterization. It's certainly possible, maybe even likely, and maybe I'm a naive dunce for thinking the nerd could be the big ladies' man, but I like to think Katrina isn't quite so conniving. Your mileage may vary.)
So indeed, the first half of huge cartoon is a fun, funny lark. But when the Halloween party starts, everything starts to change. It's nighttime. The colors are muted. The sky is overcast. There are, subtly, Jack-o-Lanterns on the scene. And from when Brom tells his ghost story on to the end, it becomes about as frightening as a kids' cartoon can get.
Despite the scrambling and clowning around with Ichabod's borrowed nag, the ride through the woods is relentlessly frightening. The Headless Horseman is one of Disney's scariest images, along with Maleficent from Sleeping Beauty, the Queen of Hearts from Alice in Wonderland, The Ghost of Christmas-Yet-to-Come in Mickey's Christmas Carol, and The Jonas Brothers.
Tying together all of the humor, horror, and 40s-style music is the legendary voice of Bing Crosby. He croons, he scats, he narrates, and he delivers lines for the characters in his rich baritone that emphasizes both the frightening and the playful parts with equal aplomb. Bing is always a welcome presence, and here he gives his all for something that must have been an odd project for him - a cartoon where he plays all the roles and sings all the songs, and that goes from comedy to horror in a short 30-minute span. Bing is just great.
It was so much fun to revisit this memory from my childhood. I don't know if Disney Channel bothers to show it anymore on Halloween - after all, they have a million original television shows, both live action and cartoon, that they can create new, safe, not-at-all-scary Halloween episodes out of until the cows come home. But I will be happy to watch this classic piece of literary horror blended with brilliant cartooning with my family for many, many Halloweens to come.
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