Disney’s “The Legend of Sleepy Hollow” is an Underappreciated Halloween Classic

The 1949 Disney film is a lot more sinister than most people probably remember.

When I was growing up, one cartoon terrified me more than any other, and that was Disney’s The Legend of Sleepy Hollow. Originally the second half of a “package film” — Disney produced quite a few of these during the 1940s as a means of cutting costs, and this one also included a short adaptation of The Wind in the Willows — by the time I was growing up it was regularly shown on its own. In fact, it wasn’t until I was all grown up that I even realized that had originally been conjoined with the adaptation of the popular children’s book by Kenneth Grahame. Every time that it came on TV, I felt a sense of dread, because I knew what was coming.

For those who haven’t seen it, The Legend of Sleepy Hollow is narrated by none other than the crooner extraordinaire Bing Crosby, whose mellifluous tones guide the viewer through this animated adaptation of Washington Irving’s classic tale about the gangly schoolmaster Ichabod Crane, who comes to the town of Sleepy Hollow and begins to develop a romance with the beautiful and wealthy Katrina van Tassel. Unfortunately for Ichabod, he’s confronted by Brom Bones, a blustering and muscular village youth who has his own ambitions where Katrina is concerned. Even more unfortunately, he runs afoul of the Headless Horseman while riding home from the autumn dance and, by the end, he has disappeared from Sleepy Hollow.

It’s hard to express just how much this film frightened me as a kid. It’s truly one of the most tightly-woven and brilliantly executed scenes that I’ve ever seen in a children’s film, and I can’t imagine that I’m the only kid who found themselves white-knuckled with fear as Ichabod tries desperately to escape from the Headless Horseman and his all-too-sharp sword. It was one of those cartoons that I absolutely dreaded watching, and I can only imagine how frustrated my mom must have been at my unwillingness to watch Sleepy Hollow except under duress.

I was reminded of this primordial fear while recently watching it with my mom. Even now, when I’m within spitting distance of 40, I still felt a faint tremor of superstitious dread as Ichabod started plodding home from the dance, for I knew what Ichabod different: that something wicked this way comes.

Now, I’ll be the first to admit that I’m not the biggest fan of most of the package films of the 1940s, most of which don’t hold up particularly well (especially compared to the classics that came before and after). In fact, I find The Wind in the Willows one of the more underwhelming of Disney adaptations, and there are, in my considered opinion, many other superior adaptations of Grahame’s novel. The Legend of Sleepy Hollow, on the other hand, is a testament to what Disney could achieve when he really put his mind to it, capturing the bit of darkness that always lurks in the American folkloric imagination.

What makes this sequence of the film particularly effective is its place in the narrative. Right before Ichabod begins his journey back home, he (and the viewer) have been treated to a rousing musical sequence in which the mischievous — and slightly malicious — Brom Bones torments the obviously frightened and flustered Crane with a rousing song about the dangers of riding home late at night. Immediately afterward, Crane and his sluggish horse make their way through the forest, and the tension slowly mounts as he encounters frogs whose croaks sound suspiciously like a chorus of “Headless Horseman” and a raven that seems to screech “Beware!”

The best part, however, comes when Ichabod mistakes the sound of cattails pounded against a rotten log for the sound of hoofbeats. After he and his slovenly horse erupt in laughter, they are joined by someone much more terrifying, the Horseman himself.

It has to be said that the Headless Horseman is a brilliantly rendered piece of animation, capable of truly stunning feats of physical action, as when he and his red-eyed steed leap from a towering hill, cape billowing like a malevolent set of wings. This is a creature that one could well believe has come straight from the pits of Hell to bring misery to the stork-like schoolmaster of Sleepy Hollow.

The terror of the Headless Horseman.

Eventually, Ichabod manages to escape from the Horseman by fleeing across the bridge, the place where, as Brom Bones sings, “his power ends.” Unfortunately for Crane, the Horseman isn’t satisfied with having chased him out of his domain, and he throws his glowing pumpkin head at him, and the screen erupts in flames before going dark.

Of course, viewers are supposed to assume that the Headless Horseman isn’t real at all, that’s he’s merely the young tough Brom Bones attempting to scare Ichabod out of Sleepy Hollow so that he can gain the beautiful Katrina’s hand in marriage (which he does). Upon my recent rewatch, however, I noticed that there’s actually a lot more ambiguity about this than meets the eye. Crosby’s narrator intones that there were many rumors that Ichabod, having fled the terrors of Sleepy Hollow, ended up marrying a wealthy widow, and the animation shows him seated around a table with a brood of children that look just like him.

However, Crosby also reminds us that the people of Sleepy Hollow know the truth about his fate, that he was “spirited away” by the Headless Horseman, never to be seen again. The film then cuts to the Horseman on his steed, laughing maniacally. It’s unclear whether this is the same demonic being that chased Ichabod or just a projection of the villagers’ devoutly superstitious belief in his part in the schoolmaster’s disappearance. This dovetails neatly with a similarly disconcerting moment earlier, when Ichabod, having had the misfortune to land on the Horseman’s steed, gazes into the ghoul’s collar and is greeted with nothing more than a maniacal laugh. The viewer can’t help but wonder: what did Ichabod see? The fact that we don’t know, and that he certainly didn’t see Brom’s head, suggests that this may, in fact, be a supernatural creature. And, even if it was Brom in the guise of the Horseman, the fact that he seems to genuinely want to hurt him — that sword of his looks awfully sharp, and he wields it with almost lethal intent — this is certainly a lot darker than most people readily acknowledge.

There is, then, a fundamental instability within the film’s own narrative about the status of the Horseman, one highlighted by the fact that Crosby’s narrator exclaims that he’s getting out of there. It’s precisely this little bit of menace that makes The Legend of Sleepy Hollow a perfect treat every Halloween.


The study of the screen.

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