Thoughts on The Legend of Sleepy Hollow

Shortly after finishing reading what is perhaps Washington Irving's most well-known work, I told my partner, Ike: "The thing about reading the classics is they're always so much weirder than the popular conception makes them out to be." The original text doesn't deviate much from the tale as I've seen/heard it play out through this or that adaptation/homage seen at such and such a time(s) in my life (so imprecise a time, in such uncalculated moments, that the recollection is swathed in dream). But, while it doesn't deviate from the tale as I've somehow internalized it (the Legend, as it were) it is still weird.

The Multiplicity of Ichabod Crane and Sleepy Hollow

Like I said, I don't know when I first encountered the story. I have a vague recollection of Disney's Ichabod - not the Disney film The Adventures of Ichabod and Mr. Toad, mind you, as I can't say with certainty that I've seen it to completion, and I have no memories of Mr. Toad - no, I just mean Ichabod Crane as depicted by Disney in that particular film. I must have seen it at some point, but I remember nothing save for this unforgettable character design - which, as it turns out, originated in the mind of Washington Irving. I was surprised (read: pleasantly horrified) to discover that Disney's Ichabod was staunchly faithful to his original description, practically lifted from the text.

The absolutely iconic Ichabod Crane.

The cognomen of Crane was not inapplicable to his person. He was tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame most loosely hung together. His head was small, and flat at top, with huge ears, large green glassy eyes, and a long snipe nose, so that it looked like a weather-cock perched upon his spindle neck to tell which way the wind blew.

Borderline body horror. A caricature of a human being, perfect for cartoon adaptation. If anything, Disney played down the full extent of Crane's bizarre physiognomy. Irving goes on to say:

To see him striding along the profile of a hill on a windy day, with his clothes bagging and fluttering about him, one might have mistaken him for the genius of famine descending upon the earth, or some scarecrow eloped from a cornfield.

In these descriptions of Crane, every detail is meant to emphasize his ludicrous character. When I read the above-quoted section to Ike, he said, "I feel like normally you'd put the genius of famine AFTER the scarecrow..." It's a perplexing choice, to be sure, but that's the point: To end the sentence comparing him to a "genius of famine" would leave a stronger impression, yes, but Irving uses anticlimax to humorous effect. The juxtaposition and particularly the order of these two images is unexpected and playfully jarring.

Irving goes to a far extreme by comparing Crane to a "genius of famine," summoning the image of an unnaturally gaunt and gangly character, with an undertone of menace as he "descends upon the earth." If the sentence ended on that note, you would be left with the impression of a frightful character. But Crane is not meant to be an intimidating person, so Irving softens the blow by evoking the image of an errant scarecrow, out of place but ultimately harmless.

It's also worth noting, I think, how the combination of concrete but cartoonish descriptions with metaphorical ones paints Crane's appearance in a nearly impressionistic style: more emotionally vivid than realistic. With this in mind, Irving's use of anticlimax takes on another meaning: simulating Crane's impression on the mind. By beginning with the "genius of famine," Irving establishes that Crane is so utterly and platonically gangly and gaunt he might - at first glance - strike fear into the hearts of onlookers. By ending on "scarecrow," we see him in a new light: unthreatening, foolish, silly.

Moreover, if a scarecrow managed to "elope" from a cornfield (blown perhaps by a particularly strong gust of Autumn wind) it might appear - at first glance, or from the corner of the eye - very much like a "genius of famine descending upon the earth." The tricks our eyes (and minds) play on us is certainly a theme of The Legend of Sleepy Hollow, and arguably the main source for its supernatural elements. More on this in the next section.

The story is full of humorous descriptions; I wish I had time to highlight them all. One of my favorites is this description of Ichabod Crane riding a horse:

He rode with short stirrups, which brought his knees nearly up to the pommel of the saddle; his sharp elbows stuck out like grasshoppers'; he carried his whip perpendicularly in his hand, like a sceptre, and as his horse jogged on, the motion of his arms was not unlike the flapping of a pair of wings.

Humorous as it remains to be, Crane's characterization can be viewed from multiple angles; he may be more reminiscent of a cartoon than a human being, but he is definitely not "flat." His quirks, both in appearance and in personality, are so peculiarly described as to vividly inspire the imagination, and in my own experience, while the image I conjured looked and behaved like no person I'd ever met, he still felt human. It is Irving's execution of this character - showing him in different situations - that makes Ichabod Crane come alive. Viewing his later actions in light of his initial characterization yields multiple interpretations, adding intrigue and depth to the character.

Take this description of his pedagogy:

Truth to say, he was a conscientious man, and ever bore in mind the golden maxim, "Spare the rod and spoil the child." Ichabod Crane's scholars certainly were not spoiled.

...he administered justice with discrimination rather than severity; taking the burden off the backs of the weak, and laying it on those of the strong. Your mere puny stripling, that winced at the least flourish of the rod, was passed by with indulgence; but the claims of justice were satisfied by inflicting a double portion on some little tough wrong-headed, broad-skirted Dutch urchin, who sulked and swelled and grew dogged and sullen beneath the birch.

Does Crane read as champion of the underdog, or a teacher on a power trip abusing his position? The implication seems, to me, that Crane identifies himself with the "puny stripling," and may be meting out justice to those who remind him of his childhood bullies - this is mere speculation, not based on text, but it's a reading I find very compelling.

Crane, an adult, seems to insert himself into schoolyard politics by taking a side. It reeks, to me, of wish fulfillment. While in the schoolhouse, he metes out punishment disproportionately against the strong, wielding his institutional power as schoolmaster like "the rod" he flogs the kids with. But as an adult, Crane still sees this dynamic of strong vs. weak playing out around him.

Before going on: It is worth mentioning the decision to specify the stronger children as Dutch while omitting the ethnicity of the weaker kids. There is a large Dutch presence throughout the story, overall, though I don't know enough about the context of Dutch-American settlements and interactions with non-Dutch Americans to form a reading out of this specific detail. Still, I think it's likely no coincidence that Ichabod Crane falls for a Dutch girl, Katrina Van Tassel, and his rival for her affections is a burly, rascally Dutchman, Brom, who bears some resemblance to the pupils Crane chooses to bully. The Dutch angle of the story (no, not that Dutch angle) is one that I would need to do more research to explore; it might warrant another essay to elaborate on it.

Strong contrasts are at the center of this story, namely the supernatural vs. the mundane and the strong vs. the weak.

Weakness is sometimes, but not always, conflated with femininity. Crane himself is somewhat effeminate, and I'm not referring to his gangly appearance. Rather, he socializes a lot with women, and seems to get along with them better than the local men. His favorite company seems to be that of old women, who share his superstitions.

He is not without his charms, being somewhat sensitive and possessing a sweet singing voice. His education tends to draw the respect of women, but earns him little from other men. Because Crane's work doesn't pay particularly well, he uses his favor with the town's women to couch-surf and get free meals. Granted, it's not really "free" as he provides soft services in exchange - singing lessons, or babysitting.

Burly Brom Van Brunt, on the other hand, is a mischievous troublemaker, yet admired by both men and woman of the town on account of his charisma.

Other men besides these two vied for the favor of Katrina Van Tassel, but in the end it narrows down to these two suitors who couldn't be more different. That Crane and Van Brunt are capable of competing in the same league is baffling to everyone, especially Brom himself. Brom tries to coax Ichabod into a physical confrontation, in which he knows there will be no contest, but Ichabod is well aware of this and never allows it to come to blows. Instead, he focuses on courting Katrina and for that matter her father, a wealthy farmer whose estate and financial assets seem to attract Ichabod to Katrina more than her fair looks.

Ichabod is smart. He is not physically strong or handsome, but he knows how to play to his strengths, or use his position, in order to get what he wants.

Ultimately, it's not enough. "The strong" triumph over "the weak." There is a great amount of ambiguity, here, but Katrina seems to reject Ichabod, and then Brom, under the guise of the Headless Horseman, seems to run him out of town - unless you take the perspective that the ghost of the Headless Horseman really did kill him.

But then what?

What's the Point?

The issue I've always had with Sleepy Hollow is that, in the end, I wasn't sure what "the point" of the story was, or what I was meant to take away. In what was perhaps the naive simplicity of childhood, I always thought that Crane was killed by the Headless Horseman (or scared dead from his superstitious fear) on the way home from the party. This seemed disconnected from the story's love triangle plot, even if Brom told Ichabod the story to scare him, which I think he did in the Disney movie.

But Ichabod Crane is not actually killed in the book, at least not definitively. He's believed dead by the townsfolk (who never recover his body, only a shattered pumpkin and his tricorn hat) but then we have this tidbit of hearsay in the end:

...an old farmer, who had been down to New York on a visit several years after, and from whom this account of the ghostly adventure was received, brought home the intelligence that Ichabod Crane was still alive; that he had left the neighborhood partly through fear of the goblin and Hans Van Ripper, and partly in mortification at having been suddenly dismissed by the heiress; that he had changed his quarters to a distant part of the country; had kept school and studied law at the same time; had been admitted to the bar; turned politician; electioneered; written for the newspapers; and finally had been made a justice of the Ten Pound Court.

It certainly sounds plausible. So things did not turn out too badly for Ichabod Crane... or did they?

The old country wives, however, who are the best judges of these matters, maintain to this day that Ichabod was spirited away by supernatural means; and it is a favorite story often told about the neighborhood round the winter evening fire. ...The schoolhouse being deserted soon fell to decay, and was reported to be haunted by the ghost of the unfortunate pedagogue and the plowboy, loitering homeward of a still summer evening, has often fancied his voice at a distance, chanting a melancholy psalm tune among the tranquil solitudes of Sleepy Hollow.

The point of Sleepy Hollow (which utterly escaped me in my youth) is liminality, multiplicity, ambiguity. Like Schrodinger's cat, Ichabod Crane is in a way both alive and dead.

Consider both of these potentialities as you read the conclusion of Brom's side of the tale:

Brom Bones, too, who, shortly after his rival's disappearance conducted the blooming Katrina in triumph to the altar, was observed to look exceedingly knowing whenever the story of Ichabod was related, and always burst into a hearty laugh at the mention of the pumpkin; which led some to suspect that he knew more about the matter than he chose to tell.

Is this the hearty laugh of a rascal, or a murderer? I find the "rascal" interpretation to be best supported by the text, as well as the most fitting somehow. The other possibility is that Brom actually went so far as to murder Crane while disguised as the Headless Horseman, or else Brom wasn't involved and the Headless Horseman really spirited poor Ichabod away. While I find it unlikely that Ichabod Crane died at all, there are a few things Washington Irving might be doing here by sowing doubt as to his fate.

First, I consider Irving's tale to be like a diptych in stereoscopic 3D:

If you close one eye, you can see a story about a simple quarrel between two men over a woman, which results in the rejection and humiliation of one and the triumph of the other.

Close the other eye and you see the sinister mists of Sleepy Hollow, its shady characters, and its Revolutionary legends enclosing Crane, an outsider, and swallowing him whole.

But you are meant to look at the whole image, with both eyes, in order to get the full picture. As a kid, I didn't really "get" Sleepy Hollow because I had one eye shut; watching the story shift in meaning as a grown-up has been part of the fun.

Coincidentally, as a kid I also used to peek over my 3D glasses, or alternate closing my right eye or my left, just to see what it really looked like - I had an awareness of, and a desire to see past, the "trick." Such awareness I lacked when it came to Sleepy Hollow: I saw what exactly what I thought I saw at the time.

Instead of an optical illusion, Irving crafts a literary one. Because this is fiction, Ichabod Crane getting spirited away by the ghost of a Hessian soldier is just as plausible as Ichabod Crane skipping town to save face.

At the same time, because this is fiction, the mundane reading is more compelling to me. You'd think it'd be the opposite, that fiction is the one place to embrace fantasy; I agree with you, but the chief fantasy entertained in nearly all literature is that of meaning and significance. If the Headless Horseman is really a spectral entity rather than a person playing a prank, what is the point of this story? Why include all that about Brom and Katrina? If we try to connect that part of the story to its ending, what did Ichabod do to merit his fate? Was the love triangle plotline an irrelevant preamble, a separate episode, a red herring?

As a fiction, the mundane reading of the story makes the most sense. In this reading, all of the events leading up to Ichabod's disappearance are relevant and connected, which we expect from well-crafted fiction. If the events of Sleepy Hollow were real life, the mundane reading would still make the most sense, but just because the alternative is impossible, not because the mundane version is more fitting. Things that happen in real life often aren't "fitting."

But isn't that strange?

By virtue of being fiction, readers are predisposed to expect events in the story to be meaningful. For a great example of a story taking full advantage of this, see Nabokov's "Signs and Symbols". But because this is fiction there is actually no logical reason to prefer a mundane reading over a supernatural one: both are equally plausible, and equally fantastic, because (it's obvious but I can't stress it enough) this is fiction, and the text itself is thoroughly ambiguous. My preference for one reading over another isn't logical: it's purely aesthetic, and that just weirds me out the more I think about it.

What does it say about me, that in growing up I tossed out the fantasy of ghosts for the fantasy of everything making sense and happening for a justifiable reason? Which fantasy is the more delusional?

I think this is the main "point" of Sleepy Hollow, and why I encourage the "Schrodinger's Crane" reading. If we favor either reading to the absolute exclusion of the other, what we have either way is a disappointing story that doesn't seem to have much of a place in the popular imagination, let alone "American Literature," if you ask me. It doesn't matter if Ichabod is dead or alive or if the Horseman was real or not - not really. If you read the story exclusively one way or the other, tell me: what's the point of reading all of that?

And yes, that question is rooted in aesthetics again. But I am still rejecting the idea that an aesthetic argument can serve as evidence to support a specific interpretation of events in a fictional story: only textual evidence can do that, and the text is ambiguous.

Rather, I am using an aesthetic argument to justify my noncommitment to any interpretation of the story itself in favor of interpreting Washington Irving's intent. Sorry Roland Barthes, but if I kill the author in this one, there isn't much substance left. The story has good prose and mood, but the narrative at face-value, whichever way you look at it, is just not very compelling. (My idea of a compelling ambiguous ending would be if both possibilities were equally interesting; see Frank Stockton's "The Lady, or The Tiger?" for a good example.)

I could just say Sleepy Hollow is bad, but I'd rather be a naively generous reader than an arrogantly lazy one.

If I assume Sleepy Hollow is art, I need to look for craftsmanship. I expected to find this in the plot, but I find the plot(s?) of Sleepy Hollow to be unaesthetic, unsatisfactory. Not particularly entertaining or edifying when taken as a whole, on its own, in a vacuum. It is literally unconventional in that it thwarts many typical story conventions. We need to take a step back, or (to use the metaphor from earlier) look at it with both eyes at once.

And if you think I'm reaching here, I again urge you to read Nabokov's "Signs and Symbols". If you take that story at face-value, it is fairly unimpressive - interesting, perhaps, but it doesn't say much. But if you accept that the craft of the story lies not in its plot but its rejection of plot, it takes on new meaning. It makes you a more self-conscious reader.

Nabokov's story features the parents of a mentally ill young man, with a conspiratorial sort of paranoia that causes him to see everything that happens to him as significant or meaningful, viewing his own life in terms of the conventions of plot. Irving's story features the acutely superstitious Crane, who is himself swallowed up in local superstition. If we accept that both stories are challenging the reader's expectations of fiction (which Nabokov's definitely is, pretty uncontroversially) then we might have to own that Irving did it with more subtlety and skill.

By encouraging parallel readings, Irving might be calling attention to our expectations about fiction, which are not grounded in reality, but in mutually agreed upon convention.

While we're all aware that fiction is fiction, this is nonetheless a little trippy. I think this is because we like tidy little narratives, and since the time of at least Aristotle we've been trying to work out the formula of a satisfying ending. I think Aristotle would say Sleepy Hollow lacks catharsis. I think it lacks a meaningful "arc," which might amount to a different way of saying more or less the same thing. We've clearly come to identify what makes a story resonate with humans, but perhaps we've catered to that desire for so long we've come to conflate satisfying that desire with the purpose of fiction itself. Is Sleepy Hollow a bad story because it doesn't give me catharsis, a narrative arc, or whatever we want to call that "high" we get from our favorite stories? If we define stories by these criteria, maybe.

Maybe stories don't have to be satisfying, though. Even if it's unconventional, something about Sleepy Hollow has had staying power in our collective imaginations.

And this longevity seems unconnected to everything I've just pointed out.

Sleepy Hollow lives on, I think, because of its spooky atmosphere and iconic characters. I think if it didn't have those elements, no one would enjoy it enough to adapt it to film, or spend the amount of time I have dragging an interpretation out of it.

The Nice Guy in the Room

I think the most interesting results of leaving the story open-ended are meta-textual, regardless of whether Washington Irving intentionally crafted it this way. But there are some in-text benefits to the Schrodinger's Crane aproach, as well. We already covered that the scene with Brom and Katrina getting married, with Brom's knowing smile at the mention of Crane, can be understood differently depending on whether or not Brom took part in the Headless Horseman incident, and whether or not Ichabod was dead.

I think we can also ask if the story is drawing a comparison between its parallel endings. Could it be that Ichabod's defeat and subsequent embarrassment are comparable to his dying and leaving behind a mournful ghost? I find this somewhat compelling when paired with the idea of Ichabod as a vengeful schoolmaster, getting back at his own bullies by inflicting punishment on others.

A very consistent feature of Ichabod Crane is his relationship to power. Crane is not a strong man. He is educated, and smart, but I don't know if he's that smart. He is not handsome. He has not been endowed with many gifts, and what he's had he's had to earn. I don't think that in itself is pathetic. I think it's actually quite respectable.

What's pathetic is that Crane seeks out positions of authority in part to exercise power over others he'd otherwise have no power over. Brom has power and influence because he is physically strong and charismatic, not because of formal authority. Brom derives power from popularity and physical strength, while Ichabod derives power largely from social position. I think it's part of why he wants to marry Katrina: her father is wealthy, and his wealth would increase his status.

It's not bad for Ichabod to want to better his lot in life. But both his position as schoolmaster and, possibly later, as justice, put him in the position of punishing others. Maybe it's just me, but I don't see him as someone driven by strong morals. I think he just likes being judgmental. He often ingratiates himself to others (mostly women) to get what he wants, so I'm not sure he sees himself as above others. But I think he has some resentment and envy towards people who he sees as having what he doesn't. Putting himself in a position to punish others to air his insecurities is the part that feels pathetic to me.

Tying it back to Ichabod as a ghost: whether Ichabod is dead or alive is less important than the fact that he is unable to move past his insecurities. Ultimately, he never gets over being bested by Brom - maybe an extension of never getting over getting bullied in school, but this isn't textual, so we'll focus on Brom as a proxy for his insecurities. Because Katrina rejects him he leaves Sleepy Hollow, finding a job that lets him exert power over others; or, after he is killed by the Headless Horseman, he haunts the abandoned schoolhouse (notably NOT the spot where he died) because he is unable to move past that place, which allowed him to exert power over others.

But does this make Sleepy Hollow an elaborate tale of nerds versus jocks? Is that really what this boils down to? Thanks, Washington Irving, I hate it.

Tale as old as time?

Seriously, though, rivalry between men who view themselves in terms of the weak and the strong is central to the story. It is about the homosocial relationships (namely rivalries) that arise out of men trying to compete on the stage of "hegemonic masculinity" which posits a man's self-worth in his physical strength and his ability to "get" women and attain status.

In the "mundane" ending, Ichabod leaves on account of his rejection and subsequent humiliation. While he was made to feel small, his education and perseverance allow him to get a more high-status job, while as far as we know Brom and Katrina just stay in Sleepy Hollow, perhaps happily married.

In this version of the story, Ichabod gets a good outcome: he leads what sounds like a successful life. I am glad this wasn't another story where we lift someone up at the expense of everyone who ever did that person wrong. That sort of spiteful irony imparts the wrong message.

...Yikes.

I think it's cool Ichabod has the courage to try his hand at wooing Katrina, even though he knows he couldn't beat Brom if it came down to a fight. But just cause he got rejected by the hottest girl in Sleepy Hollow doesn't make him undesirable, and it seems like a lot to skip town over. That, and the fact that he gets a job that involves punishing people, makes me think he's still hung up on his resentment towards Brom.

That's the good ending for Ichabod. He gets rejected, but he goes on to find success in life without having to be the strongest or the most good-looking. In the bad ending, or the supernatural ending, Ichabod is dead and his soul never moves on from the school. The only difference between the good and the bad ending is that the good ending involves Ichabod getting a good job; in both endings, he struggles to let go of what has happened to bruise his ego, but in the good ending he just finds a more prestigious place to vent his resentment than the schoolhouse.

I think we can get a lot out of comparing him to the other ghost in the story: The Headless Horseman. Legend says the Horseman was once a Hessian soldier in the Revolutionary War. His head got blown off by a cannon, and now he spends the afterlife looking for his head. Perhaps Ichabod is a restless ghost (or just a spiteful justice) because he, too, is looking in vain for something he's lost: his pride, perhaps.

I think Ichabod Crane has a number of admirable qualities, and I don't know if I'm reading too much into what I perceive as a resentment towards other men/boys. But to men/boys (and any gals and enby pals) who feel like society is against them: don't be like Ichabod Crane. Don't jump at the chance to be a bully because you have been bullied. Don't treat women as prizes. Most importantly, let go of resentment towards the Brom Boneses of the world. He's probably not your oppressor or anything, he's just a run-of-the-mill jerk, so he isn't worth all the energy. Especially if it gets self-destructive, let it go. You don't always get anything for being a nice guy, but you should be one anyway. Otherwise, you may not actually be all that nice.

By the way, there's old-timey racism in this book.

Another thing that surprised me about Sleepy Hollow was the perplexing racism. There's the dubious position of the Dutch in the story, but then there are some pretty weird descriptions of African Americans here, too, just sort of thrown in the mix.

[Class] was suddenly interrupted by the appearance of a negro in a tow-cloth jacket and trowsers, a round-crowned fragment of a hat, like the cap of Mercury, and mounted on the back of a ragged, wild, half-broken colt, which he managed with a rope by way of halter. He came clattering up to the school door with an invitation to Ichabod to attend a merry-making or "quilting frolic," to be held that evening at Mynheer Van Tassel's; and having delivered his message with that air of importance, and effort at fine language, which a negro is apt to display on petty embassies of the kind, he dashed over the brook, and was seen scampering away up the hollow, full of the importance and hurry of his mission.

Uhhhh. So the messenger is shown to be exceedingly shabby, that much is clear, but there's this comedic undertone with his "effort at fine language" which is a jab at the man's powers of speech.

I read this part to Ike and he was just as baffled as I was at "having delivered his message with that air of importance [...] which a negro is apt to display on petty embassies of the kind".

"What is he talking about?" It seemed like he was referencing some forgotten stereotype, perhaps, but it doesn't strain the mind too much to reason it's something to do with portraying African Americans as servile. The drama with which he delivers his master's party invitations implies he has been honored with some grand quest. While it is another example of Irving attempting to employ mismatched descriptions to a comedic or vivid effect, it doesn't age well at all.

Then, at the party in question, Ichabod proves himself to be a great dancer, and so:

He was the admiration of all the negroes; who, having gathered, of all ages and sizes, from the farm and the neighborhood, stood forming a pyramid of shining black faces at every door and window, gazing with delight at the scene, rolling their white eyeballs, and showing grinning rows of ivory from ear to ear.

This is just straight up minstrelsy, folks, plain and simple.

Another bonus, some neat vocab words: whilom and rantipole!

Verdict

Is Washington Irving's The Legend of Sleepy Hollow worth the read in 2022? My answer is that it depends on who you are and what you're looking for.

If you are an English language or American literature nerd, this might be worth checking out. Same for if you get a lot of value out of seeing "the classics" for yourself rather than just absorbing them secondhand through cultural osmosis.

If you want a story that gives you a snapshot into early America, this definitely fits the bill, and I think you will enjoy it. Sleepy Hollow was published around 1820, though the story takes place around 1790. The Headless Horseman himself was a Hessian soldier downed in the American Revolutionary War.

If you're a fan of gothic romance and horror such as Mysteries of Udolpho or Frankenstein, this probably won't scratch that itch. Its supernatural elements, while fantastically described, feel more tongue-in-cheek than anything. It is also lacking in the clear sense of morals and virtue which, love it or hate it, are baked into the genre. And look at hard as you want, you won't find the brooding Byronic Hero in Ichabod Crane.

My opinions, ultimately, are mixed. It's a decent story, but I still feel like there's something I don't "get" about it, and if I read it again it will probably be to try my hand again at understanding it.