Art In The Everyday: The Legend of Sleepy Hollow


There is probably no American ghost tale more famous or more widespread than The Legend of Sleepy Hollow. Learned from a young age at bed time and around campfires, the story seems just like what it purports to be: an age-old legend, belonging more to the collected population than any one author. Penned in the early nineteenth century by the American writer Washington Irving, the story was originally published as part of a series of sketches under the pseudonym Geoffrey Crayon.

The Legend of Sleepy Hollow tells the story of Ichabod Crane — a gangly, highly superstitious school teacher — and how he is driven from the small town of Sleepy Hollow by a headless, horse-riding specter. Although it’s been speculated that Sleepy Hollow was inspired by Germanic stories of headless horsemen, Irving’s take on the classic ghost tale has a decidedly American slant, owing perhaps to the author’s interest in New York history. Written during a time when Americans were trying to create an identity for themselves and their new country, Irving’s stories lent the young America its own sort of mythology. Sleepy Hollow, for example, is set in Tarrytown, a bucolic real-life location along the Hudson River in Upstate New York. The mythic horseman in Irving’s Legend was rumored to be the ghost of a Revolutionary War soldier, tragically decapitated by a flying cannonball. “Crane is also the archetypal Yankee,” notes Catherine Whalen, a professor and expert on American material culture at the Bard Graduate Center.

In addition to Rip Van WinkleThe Legend of Sleepy Hollow made Washington Irving famous — and one of the first American authors to receive international acclaim and recognition. While writers such as Nathaniel Hawthorne and Edgar Allen Poe continued the tradition of American ghost stories throughout the nineteenth century, Irving’s Sleepy Hollow — published decades earlier — set the stage for things to come. In the decades (and now centuries) that followed the 1820 publication of The Legend of Sleepy Hollow, the tale has inspired numerous iterations in literature, art, objects and film. To celebrate Halloween and this classic American legend, we’d like to share a few! — Max

Above image: The Headless Horseman Pursuing Ichabod Crane, painted by John Quidor, 1858. Property of the Smithsonian American Art Museum


Above image: The title page to the 1899 edition of Sleepy Hollow. Borders designed by Margaret Armstrong.

The full post continues after the jump . . .


Above image: Arthur Keller’s illustration of Ichabod Crane fleeing the Headless Horseman, 1906


Above Image: A 1909 postcard depicting The Legend of Sleepy Hollow. From the collection of the Museum of the City of New York


Above image: An 1863 illustration depicting Ichabod fleeing the horseman


Above image: A 1974 US stamp depicting The Legend of Sleepy Hollow. Art by Leonard Everett Fisher (via Halloween Addict)


Above image: A Sleepy Hollow Collector’s Bell, available for purchase at Sleepy Hollow Gifts


Above image: A mid-20th century edition of Rip Van Winkle and Other Stories. Available for purchase on Etsy


Above image: A 1976 Scooby-Doo children’s book in which the Headless Horseman plays a supporting role. Available for purchase on Etsy


Above image: A Headless-Horseman-themed Trixie Belden mystery from 1979. Available for purchase on Etsy


Above image: The movie poster for the 1922 film adaptation of Sleepy Hollow (via IMP Awards)


Above image: Stills from Walt Disney’s 1949 film The Adventures of Ichabod and Mr. Toad, starring Bing Crosby


Above image: Stills from Shelley Duvall’s Tall Tales and Legends’ 1987 adaptation of Sleepy Hollow. Available to watch in full on Hulu


Above image: A newspaper advertisement for a 1980 made-for-TV adaptation of Sleepy Hollow, starring Jeff Goldblum

  1. I have visited Tarrytown a few times and gone to Washington Irving’s home there. So cute and fun!

  2. Plein Jane says:

    I was on the staff of the PBS show “Wishbone” in the 1990s, and we filmed and aired a special Halloween episode of “Legend of Sleepy Hollow” in the fall of 1997. Wishbone, of course, played Ichabod Crane. I still have the prop headstone for the Headless Horseman.

    It was properly scary, but I have to admit my favorite scene is Wishbone bobbing for apples during a historic party scene. Thanks for the memories, Max!

  3. what a great post! I really enjoyed the vintage Headless Horseman images – from long ago and not so long ago! Now I want to go to Tarrytown!

  4. Bonnie says:

    I love this post Max! I’m a big Washington Irving fan since I was a little girl. Those paintings.. amazing!

  5. Elizabeth says:

    Ah, Max — you are such a wonderful writer. D*S, good work finding this guy!

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