“The Legend of Sleepy Hollow” represents Irving’s second comic masterpiece, a ghostly tale about things that go bump in the night. The specter in question here is the mysterious Headless Horseman, said to be a Hessian trooper who lost his head in a nearby battle. Each night he roams the countryside in search of it. The unlikely hero in this tale is Ichabod Crane, an itinerant schoolmaster, whose name suits him perfectly: “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.”
Irving opens his tale with a marvelous and evocative description of the lush, charming Hudson Valley region of Sleepy Hollow near Tarry Town, the delightful and dreamy atmosphere pervading the place, and the tale of the Hessian trooper’s ghost that supposedly roams near the churchyard. He then introduces the reader to Ichabod, a poor Connecticut Yankee who is very interested in marrying the wealthy, lovely, and flirtatious Katrina Van Tassel, daughter of the richest man in the area.
Ichabod’s plan is to ingratiate himself into her life, winning her hand in marriage. He arranges to teach her psalmody and is therefore permitted to visit Katrina on a regular basis at her family’s prosperous farm. His interest in Katrina, however, is less than honorable. Ichabod wants to acquire her hereditary wealth and sell it off. His chief rival is a brawny local named Brom Bones, who loves Katrina for herself. The two men despise each other; Irving adroitly contrasts Yankee opportunism with Dutch diligence. Ichabod attends a party given by Katrina’s father one night and later, on his way home, meets the terrifying Headless Horseman (Brom Bones in disguise), who drives the superstitious victim out of Sleepy Hollow forever.
Unlike “Rip Van Winkle,” which appears among the first pieces in The Sketch Book, Irving placed “The Legend of Sleepy Hollow” last and followed it in a brief piece summarizing his final thoughts on the book. It, too, is set in the Hudson Valley, but Irving’s point in this tale is markedly different. In “Rip Van Winkle” the old order gives way to the new, but the reverse is true here.
The hypocritical Yankee Ichabod is defeated by the stalwart Dutch Brom, who represents the old order. The contrast between both men could not be greater. Ichabod is a skinny, shrewd, calculating, sterile (and comic) individual, devoid of human affections, who relies on wit in his attempt to defeat his erstwhile rival. He is also a very gullible individual who believes in the supernatural, thus providing his opponent with the weapon that will destroy him. Brom, on the other hand, is a swaggering, athletic type inclined to mischievous pranks, but he does have deep romantic feelings for the beauteous Katrina. Brom is desperate to win her love, but he realizes that he cannot physically challenge his rival to a fight; hence, he devises a stratagem to prey on the schoolmaster’s fear and drive him away from Sleepy Hollow.
Although “The Legend of Sleepy Hollow” is as familiar a tale as “Rip Van Winkle” to generations of schoolchildren, it has not had much success on the stage because of the difficulty of staging the thrilling chase scene at the end between Ichabod and the Headless Horseman. It has, however, been turned into at least three motion pictures. In 1922 the great cowboy humorist Will Rogers starred in a silent-screen version retitled The Headless Horseman. For the second, in 1949, Walt Disney created a full-length animated feature with Bing Crosby as narrator. In 1999 Tim Burton’s version, Sleepy Hollow, made Ichabod Crane into a constable sent to investigate a number of murders attributed to the Headless Horseman. The tale was also made into a television film in 1980.
“The Legend of Sleepy Hollow” is an endearing and charming tale full of good humor, yet it has serious social implications. It questions whether change and progress are better than stability and order. The old virtues of the settlers are more important than those of the destroyers. Irving sides with Katrina, who has rejected Ichabod’s advances, and Brom Bones, who defeats his rival by playing on the hero’s irrational fears. Irving implies that the practical man always will defeat the dreamer. With the creation of “Rip Van Winkle” and “The Legend of Sleepy Hollow,” even if Irving had written nothing else, he would be elevated to literary greatness, because he fashioned two great American myths that perfectly symbolized American ideals and aspirations.