(Kindle eBook, Published October 2020)
Two centuries after its first publication, Washington Irving’s “The Legend of Sleepy Hollow” stands as arguably the most famous American short story ever written. Most of us have read it, or had (at least parts of) it read to us, at some point in our lives. Even those lacking firsthand experience of the narrative are likely to know its basic plot, and can recite the details of the climactic chase of Ichabod Crane by the Headless Horseman. Irving’s characters and the events of his charming ghost story no doubt have permeated pop culture, figuring in books and comics, cartoons and movies, television shows and commercial ads alike. Here, though, is where a problem emerges: “The Legend” has grown so familiar, become so mediated, that certain facts of the actual source text have been elided. For instance, it is now commonly held that the Horseman topples Ichabod by tossing a flaming jack-o’-lantern at him, but this Halloween icon does not show its glowing face anywhere in Irving’s story. The uncarved/unlit pumpkin that is employed in the climax does have special significance, which grows even clearer when “The Legend of Sleepy Hollow” is viewed alongside the author’s other work. Refocusing attention on the original text and reestablishing the story’s context (especially by aligning “The Legend” with the writings Irving ascribed to the fictitious Dutch chronicler Diedrich Knickerbocker) have been driving impulses in the construction of this e-book.
“Ultimate Annotated Edition” admittedly is a bold claim, one made in regards to the thoroughness and extensiveness of the notes. A full 116 of them are provided—outstripping, I would wager, all prior attempts to gloss Irving’s classic tale. Rather than rehearsing the attempt to locate the historical and biographical sources of the story elements (an effort admirably undertaken by books such as Henry John Steiner’s The Historically Annotated Legend of Sleepy Hollow and Gary Denis’s Sleepy Hollow: Birth of the Legend), I have adopted a more literary approach here, with an emphasis on the specific writers, works, and genres that Irving drew upon when crafting “The Legend.” Lest I be accused of Ichabod-like delusions of grandeur, I have taken the care to conduct the necessary scholarly legwork before composing these annotations. Still, the intent here is to present my evidence in an accessible manner—I am speaking to a general audience, not just those sealed off in the Ivory Tower of Academia. While seeking to inform, I want to avoid the very pedantry that Irving satirizes. By no means do I wish to analyze all the magic out of the storytelling; instead, my biggest hope is that this return tour of Sleepy Hollow leaves readers enchanted all over again.
If this happens to be your first visit to the little Hudson valley of great renown, or if this is your first time laying eyes on “The Legend of Sleepy Hollow” in quite some time, my suggestion is to begin by reading the text of the story straight through. Thanks to its captivating prose and ambiguous ending, “The Legend” invites multiple readings; at such time, the reader might turn to the (hyperlinked) notes in pursuit of deeper understanding and appreciation of Irving’s artistry. Finally, anyone interested in exploring how “The Legend” lives on can proceed to the bonus essay “Eerie Rider: The Headless Horseman’s Forays into Pop Culture”—a detailed survey of the various places the Horseman has reared his neck stump over the past 200 years, and an exploration of the reasons why the character has continued to fascinate. While the Headless Horseman undoubtedly hasn’t ridden in his last proverbial rodeo yet, my essay aspires to provide the ultimate word on the subject of his enduring post-Irving popularity.
Excerpt from the Bonus Essay, “Eerie Rider: The Headless Horseman’s Forays into Pop Culture”
He is a commercial mercenary, a typically-laconic pitchman for everything from Netflix DVDs, Dunkin Donuts, and Bud Light to M&Ms and—in the wittiest edition to-date of the “You’re Not You When You’re Hungry” ad campaign—Snickers. He works as a horrible “boss,” slinging ominous rhymes and swinging a fiery sword during the annual Hallow’s End event in the MMORPG World of Warcraft. He has lent his name to a fittingly-racing song strummed by the illustrious guitarist Joe Satriani; has had his own legendary story recorded onto a cardboard flexi-disc forming the back of a Honeycombs cereal box (although Boo Berry might have made for a more appropriate pairing). He has spread terror from Sleepy Hollow to millions of living rooms nationwide, as a deadly arch-nemesis on a hit primetime TV series.
Two centuries after first being set upon his shadowy mount by Washington Irving, the Headless Horseman appears anything but saddle-sore. Originating as a singularly-purposed and solitary figure confined to a rural area on the eastern shore of the Hudson, the hard-charging Horseman has since ridden into a state of widespread popularity.
This notorious bane of Ichabod Crane undeniably has plenty going for him. Start with his alliterative and rhythmic handle, whose dual two-syllable words create a trochaic meter (the alternate moniker given to the Headless Horseman in Irving’s tale—“the galloping Hessian of the Hollow”  works no less poetically). He makes for a fascinatingly uncanny figure, with his sentience persisting beyond the loss of life and peak body part.[E1] Skull-less yet nonetheless skillful, demonstrating equestrian abilities that would be the envy of most even if he weren’t capitally-challenged, the Headless Horseman embodies paradox. The black-cloaked rider is at once majestic and macabre, impressive in stature yet disturbingly enigmatic. Ichabod can’t help but sense “something in the moody and dogged silence of this pertinacious companion that was mysterious and appalling” (364), and that’s even before discovering the foe’s headless condition. The Horseman’s quintessential inscrutability—one cannot read his visage or hear him give voice to his thoughts—renders him that much more unsettling a sight. His overshadowing presence is reinforced by the lofted position (consider the popular depiction of him straddling a rearing steed) in which he is commonly beheld.
These various aspects, however, do not furnish a full explanation of the incredible and enduring appeal of Irving’s Headless Horseman; certainly, there must be more to account for the figure’s rise from short-story bogy to “worldwide icon” (Kruk 11). The following essay will explore the manifold pop-cultural manifestations of the supposed ghostly leftover from the American Revolution. The goal here is to range beyond a compilation of Wikipedia-type trivia, to offer more than a broad survey of the Horseman’s appearances in an assortment of media. Not content merely to catalogue the where and when, the essay will delve into how (the Horseman’s image and mythos have evolved) and why (this midnight rider strikes such a chord with audiences) and what (factors established the Horseman as a modern October monarch, a figure synonymous with the Halloween season). But in order to best attend to the Horseman’s growth over the years, we must first travel back to his literary birthplace in the rustic acres of Sleepy Hollow.
The Horseman initially crops up four paragraphs into “The Legend of Sleepy Hollow” (first published in 1820 in Irving’s The Sketch Book of Geoffrey Crayon, Gent.). After emphasizing the tranquility of the locale and its denizens’ penchant for marvelous belief (“the whole neighborhood abounds with local tales, haunted spots, and twilight superstitions”), the narrator posits that the “dominant spirit […] that haunts this enchanted region and seems to be commander-in-chief of all the powers of the air is the apparition of a figure on horseback without a head” (339). The figure “is said by some to be the ghost of a Hessian trooper, whose head had been carried away by a cannonball, in some nameless battle during the Revolutionary War, and who is ever and anon seen by the country folk, hurrying along in the gloom of night, as if on the wings of the wind” (339-40). Two parts of this initial description are noteworthy. First, the Horseman is presented as an entity more airy than earthbound, ethereal rather than hefty. Second, notice how the narrative equivocates (“said by some,” “some nameless battle”), marking itself with non-commitment and vagary. The provenance (beheaded Hessian) of this restless spirit—a backstory largely accepted as fact in subsequent recursions to Irving’s tale—is here offered only as a possible explanation. There’s a perceptible playfulness to the narrative’s approach to the subject of the Horseman’s origins, with Irving punningly referencing “the floating facts concerning this specter” (340), oh-so-carefully “collect[ed] and collat[ed]” by local chroniclers. For all their documentary rigor, these “most authentic historians” can at best merely “allege [emphasis mine] that the body of this trooper, having been buried in the churchyard, the ghost rides forth to the scene of the battle in nightly quest of his head.”
Two centuries’ worth of interpolating representations have succeeded in fleshing out a spectral frame and solidifying the image of the Headless Horseman in public consciousness. Every visible rendition (in paintings, on book covers, as Halloween decoration, etc.) makes it easier to forget that the original Horseman of “The Legend of Sleepy Hollow” is established as an apparition, a figure flitting before the respective mind’s eyes of superstitious villagers. Still, over the years there have been plenty of works that have emphasized the phantasmic nature of the Horseman. Prime among these is the 1922 silent film The Headless Horseman, starring Will Rogers. Following an intertitle citing the legendary decollated rider as the “famous chief of [Sleepy Hollow’s] legion of ghosts,” a caped, skeletal specter is shown (in what must have seemed an amazing special effect for that time period) rising from the grave and summoning a ghostly horse. In “The Headless Horseman Rides Again,” a comic-book story featured in a 1973 issue of Supernatural Thrillers, the titular spirit is shown with a glowing bony frame and a flaming skull in his hand. Exposed midway through as a hoax (a “phosphorescent costume” donned by the gangster Bones Bullinger in an attempt to extort protection money from local businessmen), the Horseman’s paranormal status is restored in the story’s final panel; the figure that rammed the hero’s car off the bridge in Sleepy Hollow must have been the authentic ghost, considering that Bullinger was found scared to death hours earlier.[E2] “The Tale of the Midnight Ride,” a 1994 episode of the TV series Are You Afraid of the Dark?, posits both the Horseman and Ichabod as ghostly riders who return to Sleepy Hollow every Halloween. When nerdy teen newcomer Ian directs the revenant Ichabod which fork in the road to take, he unwittingly sics the “demon ghost” of the Horseman on himself. The green-glowing Horseman in the 2013 animated short The Legend of Smurfy Hollow is also presented as conspicuously spectral (although the rider proves at tale’s end to be just a goat that Papa Smurf glamoured to stymie Gargamel). And a paranormal apotheosis is perhaps reached in Jack Prelutsky’s “Headless Horseman,” a strikingly macabre children’s poem that elevates its eponymous antagonist from regional ghost to Grim Reaper—a black-robed, scythe-wielding, skeletal “minister of death” (line 15), that “rides the wind alone” (line 17) searching for unfortunate souls to usher out of this world.
Intangibility defines Irving’s original figuration of the Horseman, both as purported ghost and subject overtly born of discourse. The Horseman’s most specific haunt is the hearth rather than the hollow, his truest mode of conveyance not some nightmare steed but the nocturnal storyteller: “this legendary superstition,” Irving writes, “has furnished materials for many a wild story in that region of shadows, and the specter is known at all the country firesides, by the name of the Headless Horseman of Sleepy Hollow” (340). Irving, in fact, frames the entire “Legend” as narrative and foregrounds the process of oral transmission. The manuscript of the tale was “FOUND AMONG THE PAPERS OF THE LATE DIEDRICH KNICKERBOCKER” (338), the reader learns at the outset, but the identity of the first-person narrator grows slippery when the Postscript belatedly reveals that Knickerbocker heard the preceding story told by a “pleasant, shabby, gentlemanly old fellow” (368) during a Manhattan corporation meeting (the text remains vague about Knickerbocker having offered a verbatim transcription or his own translation). An argument can be made that it is the form as much as the content of Irving’s tale that has launched the long, formidable career of the Horseman. A story about storytelling, a legend reflecting upon the fascination with, and dissemination of legend, the piece speaks to a basic human desire for narrative.
Testament to the impact of Irving’s structure is given by countless retellings of “The Legend of Sleepy Hollow.” Both “The Tale of the Midnight Ride” and The Legend of Smurfy Hollow, for instance, are framed as spook stories shared around a campfire. The act of narration is prominent even in works that make only passing reference to the tale. The Curse of the Cat People, a nominal 1944 sequel to the hit supernatural thriller Cat People that is somewhat-curiously set in Tarrytown (not far from where producer Val Lewton grew up), features a scene in which an aged, eccentric ex-actress entertains the film’s young female protagonist Amy with a dramatic drawing-room recitation of the story of “The Headless Horseman.”[E3] Sleepy Hollow meets Mayberry in “A Wife for Andy,” a 1962 episode of The Andy Griffith Show in which the amiable sheriff reads “The Legend” aloud as a bedtime story to Opie. The scene is played for comic effect (Andy keeps getting interrupted by unexpected visitors at his door) yet highlights how Irving’s tale passes from generation to generation. A telling rehearsal of Irving can also be found in Peter Straub’s self-reflexive 1979 magnus opus Ghost Story, which revolves around the frightful fireside tales passed among the haunted members of the Chowder Society. Surely it is no coincidence that the first ghost story told in the novel is a variation on “The Legend of Sleepy Hollow” (ultimately mashed-up with The Turn of the Screw). The narrator recounts his experience decades earlier as a teacher in a one-room schoolhouse (51) in a rural New York village and his encounter with the malevolent revenant of a man that perished from a grievous head injury (suffered when his younger siblings deliberately “knocked the ladder out from under him”  as he worked on repairing the schoolhouse’s rain gutter). How thematically appropriate that Straub’s complex narrative of spook tales come to terrifying life hearkens back to Irving’s tale of a schoolmaster harassed by a seemingly all-too-real local legend.
“The Legend of Sleepy Hollow” has been adapted by a broad range of authors, from fledgling self-publishers (the public domain status of Irving’s text enabling the marketing of fan fiction) to bestselling novelists. Somewhat surprisingly, one writer who has not made extensive reference to “The Legend” is Straub’s fellow horror-genre figurehead and occasional collaborator, Stephen King. Passing mention (for the purpose of comic relief) is given in Pet Sematary: “Ellie began to arrive home laden with Halloween decorations she had made at school and entertained Gage with the story of the Headless Horseman. Gage spent that evening babbling happily about somebody named Itchybod Brain” (84). An even briefer nod occurs in the King story “The Little Green God of Agony,” when a gangly character reminds “Kat of a picture she’d seen once of Washington Irving’s schoolteacher, Ichabod Crane” (386). The opening of the film version of The Dead Zone shows Christopher Walken assigning the Irving story to his high school students (“You’re gonna like it; it’s about a schoolteacher who gets chased by a headless demon,” says the actor who years later would famously take on the role of the Horseman himself), but the source novel features no such scene. King, though, can be seen to make witty allusion to Irving in the October-set Under the Dome, when describing an attempted missile strike against the eponymous obstacle: en route to its target, the missile “imploded a roadside stand in Tarker’s Hollow, sending boards and smashed pumpkins flying into the sky. The boom followed, causing people to fall to the floor with their hands over their heads” (341).[E4]
[E1] In his study On Monsters, Stephen T. Asma speculates: “Is a headless horseman particularly scary when compared with a moustache-less man or a hatless man because we’ve never experienced such an anomaly, or because we have some instinctual understanding that heads are essential for human life, so that the headless monster is an instance of multiple ‘category jamming,’ both morphologically incoherent and also transgressing the categories of the animate and the inanimate?” (184). Literary critic Roger Luckhurst, in his BBC.com essay “The Horror of the Headless Horseman,” adds: “Since we increasingly associate identity with the brain (and less so with the heart), the act [of beheading] strikes at the very essence of selfhood—of memory and rationality.”
[E2] A preceding comic-book story, 1954’s “The Haunting of Sleepy Hollow” (reprinted in a March 1974 issue of Crypt of Shadows), presents similar twists involving human masquerade and supernatural mayhem. During an excursion to Sleepy Hollow, investment broker Sam Langhorn attempts to scare off his junior partner—and chief rival for the affections of the lovely Sally Klee—by dressing up as the Headless Horseman. Mid-impersonation, though, Sam himself encounters the Horseman, who brains him with his severed head (Sam ends up in the insane asylum after recounting the incident). Of course, Sam’s attacker was a disguised Joe, acting out a plan that he and Sally concocted. But as the pair of money-hungry schemers gloat over their ghostly ruse while driving out of town, they spot the “real” Headless Horseman, who promptly fires his head and causes their car to crash off a bridge.
[E3] Mrs. Farren’s monologue: “On the dark nights, on the stormy nights, you can hear him as he passes by like the wind, and the flapping and fluttering of his great cloak beating like gaunt wings. And the thundering of his horse’s hooves is loud and loud and louder. At the midnight hour, down the road that leads to Sleepy Hollow, across the bridge he goes galloping, galloping, galloping. Always searching, always seeking. And if you stand at the bridge at the wrong hour, the hour when he rides by, his great cloak sweeps around you. He swings you to his saddlebow, and then forever you must ride. And always his cold arms around you, clasping you into the cavity of his bony chest. And then forever you must ride, and ride and ride with the Headless Horseman.” Such fine imagery to fill a child’s mind with, Mrs. Farren!
[E4] King’s “Tarker’s Hollow” construction demonstrates another way in which Irving’s “The Legend of Sleepy Hollow” resonates—via verbal echo in property titles and place names. Consider: the 1959 film Ghost of Dragstrip Hollow; Manly Wade Wellman’s 1964 young-adult novel The Master of Scare Hollow; Dark Hollow in Jonathan Maberry’s Pine Deep Trilogy (Ghost Road Blues , Dead Man’s Song , Bad Moon Rising ); LeHorn’s Hollow in Brian Keene’s novels Dark Hollow (2006) and Ghost Walk (2008).
To read the full essay, as well as the text of Irving’s classic story and my extensive annotations to it, head over to Amazon and download your copy of The Legend of Sleepy Hollow: Ultimate Annotated Edition.