The Legend of Sleepy Hollow, Washington Irving - Essay

Washington Irving


“The Legend of Sleepy Hollow” Washington Irving

The following entry presents criticism of Irving's short story “The Legend of Sleepy Hollow” (1819).

Considered the first professional man of letters in the United States and the first American author to win recognition abroad, Irving is noted for his contribution to the short story genre. In his most acclaimed achievement, The Sketch Book of Geoffrey Crayon, Gent. (1819–20), he created charming sketches, tales, and travel reminiscences. Widely read in its time, the book is remembered for the short stories “Rip Van Winkle” and “The Legend of Sleepy Hollow.” In the latter of these tales—which details the run-in of a Connecticut schoolmaster, Ichabod Crane, with a headless horseman—Irving wove elements of myth, legend, folklore, and drama into a narrative that achieved almost immediate classic status. Critics generally agree that “The Legend of Sleepy Hollow” provided a model for the modern short story and introduced imagery and archetypes that enriched national literature. While Irving's other historical writings are valued for their graceful prose style and historical interest, critics generally agree that “The Legend of Sleepy Hollow” is—along with “Rip Van Winkle”—his most lasting artistic achievement.

Plot and Major Characters

“The Legend of Sleepy Hollow” opens with a description of the Dutch New York community of Sleepy Hollow, located in a rural valley near the Hudson River. Irving introduces the tall, lanky schoolmaster Ichabod Crane as a figure of mild derision, a hard-nosed itinerant Yankee from Connecticut who takes himself too seriously and possesses an enormous appetite despite his slight build. Proud of his erudition, at least in comparison to the rustics he encounters in Sleepy Hollow, Crane is described as “an odd mixture of small shrewdness and simple credulity.” He quickly discovers Katrina Van Tassel, the lovely daughter of a well-to-do Dutch farmer, Baltus Van Tassel, and resolves to win her heart. His principal rival, Brom Van Brunt, nicknamed Brom Bones, is a burly outdoorsman, strong and somewhat arrogant but with a well-developed sense of humor. Realizing that he cannot best Bones in feats of physical prowess, Crane sets out to woo Katrina by making regular visits to the Van Tassel farmhouse as a singing-master. Over time the competition between Crane and Bones intensifies.

At an autumn party at the Van Tassel home, Crane endeavors to impress Katrina with his singing and dancing. As he seems to gain the upper hand over Bones the conversation turns to local ghost tales—principally that of the Headless Horseman, an apparition of a decapitated Hessian soldier that haunts the area. Bones entertains the crowd by telling of his own adventure with the Horseman; later Crane recites extracts from the works of his favorite author, Cotton Mather. As the party winds down, Crane speaks with Katrina, but his advances are rebuked. Crestfallen, he departs on his horse. Shortly thereafter, while traveling through the darkness, Crane encounters the ghostly Hessian soldier who chases the schoolmaster until the frightened man is thrown from his steed. The following morning, the horse is found without its saddle or rider near the smashed remains of a pumpkin. Crane is never seen again in Sleepy Hollow, though a rumor spreads that he has become a lawyer and a judge in another town. The tale is retold of his harrowing confrontation with the Headless Horseman, which produces a spirited laugh from Brom Bones whenever the pumpkin is mentioned. Irving closes the tale with a postscript describing the original narrator of the story, “one tall, dry-looking old gentleman” who draws some conclusions from the extravagant yarn, but finally claims, “I don't believe one-half of it myself.”

Major Themes

Thematic analyses of “The Legend of Sleepy Hollow” generally focus on the character of Ichabod Crane and the satirical implications of his rivalry with Brom Bones. Many critics maintain that Crane represents the outcast artist-intellectual in American society; although he has been considered, conversely, as a caricature of the acquisitive, scheming Yankee Puritan, a type that Irving Iampooned regularly in his early satirical writings. Additionally, the work is seen as a regional contrast between Yankee Connecticut and Dutch New York, the latter personified in the figure of the backwoodsman Brom Bones. Other commentators have suggested that Crane represents a morally corrupt capitalist figure. Also, the tension between imagination and creativity versus materialism and productivity in nineteenth-century America is considered a significant theme in the story.

Critical Reception

Although much of Irving's fiction is today regarded as little more than petty and derivative, many critics agree that Irving did much to establish the American short story in 1819 with “The Legend of Sleepy Hollow.” Commentators concur, moreover, that Irving set the artistic standard and model for subsequent generations of American short story writers with the tale. Among the technical innovations ascribed to “The Legend of Sleepy Hollow” include the integration of folklore, myth, and fable into narrative fiction; setting and landscape as a reflection of theme and mood; and the expression of the supernatural and use of Gothic elements.

Principal Works

The Sketchbook of Geoffrey Crayon, Gent. [as Geoffrey Crayon] 1819-20

Bracebridge Hall; or, the Humorists: A Medley [as Geoffrey Crayon] 1822

Tales of a Traveller [as Geoffrey Crayon] 1824

The Alhambra [as Geoffrey Crayon] 1832

The Crayon Miscellany [as Geoffrey Crayon 1835

Salmagundi; or, The Whim-Whams and Opinions of Launcelot Langstaff, Esq., and Others [With William Irving and James Kirke Paulding] (satirical essays) 1807-08

A History of New York, from the Beginning of the World to the End of the Dutch Dynasty [as Diedrich Knickerbocker] (historical parody) 1809

A History of the Life and Voyages of Christopher Columbus (biography) 1828

A Chronicle of the Conquest of Granada (history) 1829

A Tour on the Prairies (travel sketches) 1835

The Works of Washington Irving. 15 Vols. [author's revised edition] (essays, short stories, sketches, history, and biography) 1848-51

Oliver Goldsmith (biography) 1849

The Life of George Washington (biography) 1855-59

Daniel G. Hoffman (essay date 1961)

SOURCE: “Prefigurations: ‘The Legend of Sleepy Hollow’,” in Form and Fable in American Fiction, Oxford University Press, 1961, pp. 83-96.

[In the following essay, Hoffman explains how “The Legend of Sleepy Hollow” dramatizes a conflict between two cultures—those of the Yankee city-dweller and the backwoodsman—that was to become a major theme in American literature.]


The first important literary statement of the themes of native folk character and superstition was made, fittingly enough, in the first literary work by an American to win worldwide acclaim. When The Sketch Book of Geoffrey Crayon, Gent. appeared in London in 1819, its author became the first of a long series of expatriate Americans who found their native roots all the more poignant for viewing them from a distance.

Washngton Irving was fortunate, granted his special though restricted gifts, to be alive and in England at that moment in the history of literature. He sought out, and was taken up by, Sir Walter Scott, who was showing how the sentiment of nostalgia for the past could infuse fiction and become its informing principle. In his novels Scott projected that sense of historical continuity which formed a curious undercurrent of sensibility even before the Romantic movement began. Little though the Augustans attended the medieval or more recent past, there were important eighteenth-century successors to such early antiquarian works as Sir Thomas Browne's collection of Vulgar Errors (1648) and Samuel Pepys' collection of broadside ballads. Bishop Percy's Reliques of Ancient English Poetry (1765) and John Brand's Observations on the Popular Antiquities of Great Britain (1795) laid the groundwork for the two directions British folklore study has followed ever since. Scott took his prominent place in both with his ballad collection, The Minstrelsy of the Scottish Border (1802) and his comprehensive Letters on Demonology and Witchcraft (1830). Much more influential, however, than these formal studies in introducing a whole generation of readers—and authors—to such materials was his use of folklore in his own fiction. One of Scott's earliest and most popular disciples along this line was a young American littérateur, the London representative of P. E. Irving & Co., New York dealers in hardware.

Washington Irving was already something of an antiquary. His early Knickerbocker's History of New York reveals him to be enchanted with the very past he satirized. In The Sketch Book Irving used several themes to which he would again and again recur: the Gothic tale in the German manner of ‘The Spectre Bridegroom,’ the antiquarian nostalgia of the four sketches on English Christmas customs, the character sketch of ‘The Village Angler.’ The two selections destined for most enduring fame, however, were careful reconstructions of the scenes of Irving's own boyhood in the Dutch communities of the Hudson Valley. One of these retells a German folktale in this American setting, in which Rip Van Winkle sleeps away his twenty years after a heady game of bowls with the ghostly crew of the Half-Moon. In the other tale, ‘The Legend of Sleepy Hollow,’ Irving brought into belles-lettres for the first time the comic mythology and folk beliefs of his native region. In Ichabod Crane and Brom Bones he dramatized that clash of regional characters—the Yankee versus the Backwoodsman—which would soon become a major theme in our literature, as well as a continuing motif in a century and a half of folktales, and in our national history.

It is surprising that the extent to which Irving drew upon native folklore has scarcely been acknowledged. The chief reason for this seems to be Henry A. Pochmann's convincing demonstration, in 1930, of the extent of Irving's indebtedness to his German contemporaries. Stanley T. Williams, in his definitive biography, gives us a further exploration of Irving's methods of composition.1 When we see the extent to which Irving depended on other men's books, often translating without acknowledgment, we can understand why recent critics are reluctant to grant him credit for originality in interpreting American themes.

The foremost students of American humor have strangely overlooked ‘The Legend of Sleepy Hollow.’ Walter Blair does call it ‘a characteristic piece of American humor,’ but his remark is relegated to a footnote. And Constance Rourke, writing with her usual felicity, remarks that ‘in the Knickerbocker History and in Rip Van Winkle Irving created a comic mythology as though comic myth-making were a native habit, formed early …... But his Dutch people were of the past, joining only at a distance with current portrayals of native character.’2 Why did Miss Rourke not mention ‘Sleepy Hollow’? I do not know; but I hope to show that in Ichabod and Brom Bones, Irving gave us portrayals of current native character projected backwards in time, rather than merely historical types unrooted in contemporary folklore.

There are of course good reasons why Brom and Ichabod have not been so recognized. For one thing, Irving's style is hardly what we expect in a folk document. For another, the Hudson Valley Dutch have long been thought an alien people by the Anglo-Saxons who conquered, surrounded, and outnumbered them. But the third and principal reason is Irving's own treatment of his Dutch materials. Almost everywhere except in ‘The Legend of Sleepy Hollow’ he deliberately altered the traditional characteristics of the Dutch for the purposes of his own fiction. As a consequence of Irving's popularity and of widespread ignorance of what the Dutch were really like, his caricatures were widely accepted as portraits of the Dutch-Americans. Paulding, writing The Dutchman's Fireside twenty-two years after the Knickerbocker History, imitated his friend in attributing chuckleheadedness and indolence to the brothers Vancour. In Cooper's Satanstoe (1845), however, we get a more realistic picture of the Dutch; his Guert Ten Eyck amply fulfills the historian Janvier's description: the Dutch ‘were tough and they were sturdy, and they were as plucky as men could be.’3 Only in ‘The Legend of Sleepy Hollow’ did Irving give a Dutchman these attributes; everywhere else he made them fat, foolish, pompous, and pleasure-loving. Here his usual Dutchman does appear (Van Tassel), but only in the background. Brom Bones is his realistic Dutch frontiersman, who meets and bests a Yankee in the traditional conflict of our native folk humor. Why did Irving choose this theme, so different from his usual preoccupations?

When we admit his dependence upon books, we must look at the kinds of authors on whom he depended. Othmar and Musaeus were collectors and redactors of folktales and märchen. Irving knew personally a third folklorist, Dr. Karl Böttiger, ‘who undoubtedly was able to give him expert advice on his folklore studies.’4 Wherever Irving went he collected popular sayings and beliefs; he was prepossessed by a sense of the past, and recognized the power—and the usefulness to a creative artist—of popular antiquities. Brom and Ichabod had their beginnings in local characters he had known as a boy;5 what made them take their singular form, however, was the direction in which Irving's imagination impelled them. And that direction was toward the fabulous. The fabulous was Irving's milieu.

In a reminiscence twenty years after The Sketch Book, Irving revealed that Diedrich Knickerbocker had learned the legend of Sleepy Hollow from an old Negro who gave him ‘that invaluable kind of information, never to be acquired from books,’ and from ‘the precious revelations of the good dame at the spinning wheel.’6 Of Musaeus' Volksmärchen he says nothing. But he may well indeed have heard such stories in the old Dutch chimney corners. H. W. Thompson recounts similar motifs in York State folklore: nightly visitations by a shrieking woman ‘tied to the tail of a giant horse with fiery eyes’; and ‘a curious phantom … uttering unearthly laughter, lights shining from her finger tips.’ There were revenants aplenty in Catskills. Still another important part of Dutch folk culture was the lusty practical joking7 which Cooper used in some of the most spirited pages in Satanstoe. Both aspects of Dutch folk life—the villagers' superstitions and their humor—are immortalized in ‘The Legend of Sleepy Hollow.’


Irving sets his story in a folk society: ‘It is in such little retired Dutch villages … that population, manners, and customs remain fixed; while the great torrent of migration and improvement, which is making such incessant changes in other parts of this restless country, sweeps by them unobserved.’ And again: ‘The neighborhood is rich in legendary lore … Local tales and superstitions thrive best in these sheltered long-settled retreats.’ Into this community comes Ichabod Crane, ‘a native of Connecticut, a State which supplied the Union with pioneers for the mind as well as for the forest.’ Ichabod is Irving's Connecticut Yankee, the fictional ancestor of Mark Twain's Hartford mechanic. But his nearer descendants are Sam Slick, Jack Downing, Hosea Biglow. Before any of these was born in print Ichabod had already been a country teacher, a singing master, a sometime farmer; later he is to undergo still further metamorphoses which link him still more closely to these heroes of popular legend and literature. Like Ben Franklin, like Hawthorne's Holgrave, like the schoolmaster in Snowbound and Melville's marvelous Confidence Man, he was a jack of all trades. Metamorphosis is always magical, but now, in an egalitarian society, the magic is the power of self-reliance, not of Satan.

Ichabod's native shrewdness and perseverance are somewhat compromised by his credulity. ‘No tale was too gross or monstrous for his capacious swallow.’ Ichabod devoutly believed in all the remarkable prodigies retailed in Cotton Mather's History of New England Witchcraft (that is, the Magnalia Christi Americani). There he found spectral ships manned by ghostly women, heretics giving birth to monsters, revenants pursuing the innocent with invisible instruments of torture. But of all the ghostly tales in the valley, the one Ichabod Crane most liked to hear was that of the Headless Horseman.

Meanwhile, we remember, Ichabod falls in love with Katrina Van Tassel; more exactly, seeing her father's prosperous farm, he envisages ‘every roasting pig running about with a pudding in his belly, and an apple in his mouth.’ Considerations of this sort lead Ichabod into a most interesting reverie: he imagines ‘the blooming Katrina, with a whole family of children, mounted on the top of a wagon loaded with household trumpery, with pots and kettles dangling beneath; and he beheld himself bestriding a pacing mare, with a colt at her heels, setting out for Kentucky, Tennessee, or Lord knows where.’ Here we have Ichabod Boone—Connecticut's pioneer of the wilderness as well as of the mind. Traditionally the American frontiersman has resented the mercantile...

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Robert A. Bone (essay date 1963)

SOURCE: “Irving's Headless Hessian: Prosperity and the Inner Life,” in American Quarterly, Vol. XV, No. 2, Pt. 1, Summer, 1963, pp. 167-75.

[In the following essay, Bone considers the theme of materialism in “The Legend of Sleepy Hollow.”]

While the body of this essay is concerned with “The Legend of Sleepy Hollow,” I have tried to touch upon a central theme in our national letters: the relentless pressure of commodities on the American imagination. Walden is the classic statement of this theme. Thoreau went to the woods to escape the pressure of house and barn and mortgage; to free his soul from the tyranny of commodities. Since his aim was to...

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Martin Roth (essay date 1976)

SOURCE: “Post Mortem Effects,” in Comedy and America: The Lost World of Washington Irving, Kennikat Press, 1976, pp. 155-69.

[In the following excerpt, Roth examines the conflict between “the active and the imaginative life” in “The Legend of Sleepy Hollow.”]

“The Legend of Sleepy Hollow” is Irving's last attempt to preserve a festive America. Like The History and “Rip Van Winkle,” it is a tale of a Yankee invasion, but in it the Yankee is temporarily defeated, and his defeat is due primarily to the Yankee-American inability to assign any value to the world of dreams and imaginings. There is a hint of this theme toward the end of “Rip Van...

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Albert J. von Frank (essay date 1987)

SOURCE: “The Man that Corrupted Sleepy Hollow,” in Studies in American Fiction, Vol. 15, No. 2, Autumn, 1987, pp. 129-43.

[In the following essay, Frank describes Ichabod Crane as a morally destructive force that enters Sleepy Hollow.]

Washington Irving's reputation as a genial writer—as, indeed, America's most genial writer—has been firmly established for a century and a half, despite general agreement that his most enduring works are satires. Knickerbocker's History maintains its good humor largely by making its narrator appear foolish, but it is harder to say what keeps “The Legend of Sleepy Hollow” from seemingly overtly caustic, since in...

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Raymond Benoit (essay date 1996)

SOURCE: “Irving's ‘The Legend of Sleepy Hollow’,” in The Explicator, Vol. 55, No. 1, Fall, 1996, pp. 15-17.

[In the following essay, Benoit explores Ichabod's loss of the imaginative bond between man and the world in “The Legend of Sleepy Hollow.”]

“There used to be gods in everything, and now they've gone … all the lonely summer night's become but fact” (19). These lines from Howard Nemerov's poem “The Companions” could have served as an epigraph for “The Legend of Sleepy Hollow,” for that legend is ultimately concerned with the loss of wonder and of a sense of life-as-mystery in the slow unraveling of imaginative attachment between man and...

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Further Reading


May, Charles E. “Metaphoric Motivation in Short Fiction: ‘In the Beginning Was the Story.’” In Short Story Theory at a Crossroads, edited by Susan Lohafer and Jo Ellyn Clarey, pp. 62-73. Baton Rouge: Louisiana State University Press, 1989.

Examines “The Legend of Sleepy Hollow” as part of an assessment of the early development of the short story in American literature.

Piacentino, Ed. “‘Sleepy Hollow’ Comes South: Washington Irving's Influence on Old Southwestern Humor.” The Southern Literary Journal XXX, No. 1 (Fall 1997): 27-42.

Considers the impact of “The Legend of Sleepy Hollow”...

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