The Legend of Sleepy Hollow, on Odyssey Network
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This aired in 1999, but I didn't see it until 2019, on DVD. I should say I don't think I've ever actually read Washington Irving's story, so I don't know how closely this adheres to it, though I suspect it's quite likely closer to it than most of the other adaptations I've seen. It begins with a man named Knickerbocker arriving at a pub in the town of Sleepy Hollow. He tells the locals that he travels around, recording stories that people tell him in his journal. So they tell him the story of their own local legend...
That story begins with a man named Ichabod Crane arriving in Sleepy Hollow, hoping to get a position as a school teacher. Which he does, but only because no one else wants the job. And no one in town much cares whether their kids go to school or not. But he also organizes a church choir and teaches some of the local women to sing. Most notable among them is Mrs. Van Tassel, whose husband is the richest person in town. (But from a modern perspective, that's not saying much.) Ichabod's main interest is wooing the Van Tassels' daughter, Katrina (Rachelle Lefevre). As the old folks telling the story to Knickerbocker say, she was the most beautiful girl in town, and basically every single man wanted to be with her, but she was dating a blacksmith named Brom Bones. However, Brom wanted to move away from Sleepy Hollow and make his own fortune somewhere even farther from civilized society than that small town, while Katrina wanted to travel to more cultured places; especially Amsterdam, which is where the founders of Sleepy Hollow had come from. So it's not hard for Ichabod to ingratiate himself with Katrina, since he himself was more cultured and better educated than anyone in town. (Though I dare say not everything he claimed to know was accurate.) Meanwhile, Ichabod claims not to be afraid of supernatural things (saying he knows all about them because he read a book by Cotton Mather). But it's obvious that he actually is scared of such things. Especially after learning the local legend of the Headless Horseman.
Well, I don't want to say too much else about the plot. Except that for the most part, there's nothing scary or Halloween-ish about it, and I'm not even sure there's anything supernatural. Most of the movie is just about character development and interactions, and different motivations. The climax of the movie involves Ichabod traveling home from a harvest celebration, and encountering the Headless Horseman... though that seemed to be a prank played by Brom and at least one of his friends. It's possible the real Headless Horseman shows up, but the reason I'm not convinced of that is because throughout the film, there are several times we see Ichabod's vivid imaginings, most of which are pleasant for him. It's not hard for me to believe this final, decidedly unpleasant encounter might have been just another one of those daydreams. In any event, I enjoyed the movie for its focus on the characters, particularly Katrina. She's obviously intelligent and strong-willed, with surprisingly modern ideas and sensibilities, for her time. And easily the most likable character in the story.
movies: The Adventures of Ichabod and Mr. Toad *
TV: The Legend of Sleepy Hollow (1999) * The Hollow * Sleepy Hollow