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Five Reasons to Teach "The Legend of Sleepy Hollow" and Other Short Stories by Washington Irving

American Literature Five Reasons To Teach Series Short Stories

Legend of Sleepy Hollow

When the leaves start to change and the weather gets a bit cooler, that means it’s almost time for my go-to Halloween story:  Washington Irving’s “The Legend of Sleepy Hollow.” In the lineup of American authors, I feel like Irving gets short shrift. Sure, his stories aren’t super deep, but they’re fun, which should count for something! They are also some of the first works that can be considered distinctly American. Before I get too far ahead of myself, here are five reasons to teach the short stories of Washington Irving.

  1. Washington Irving was America’s first celebrity writer. In the early 1800s Europeans were a writer’s primary audience, and Europeans would only read the writing of fellow Europeans. American writers were considered illiterate hacks—that is, until Irving came onto the scene. Telling stories with American flair for the first time, Irving’s works became an instant hit with Europeans and legitimized American Literature. Sidenote: There’s a debate about whether Irving or James Fenimore Cooper was the first author to popularize American Literature, but if you’re going solely by dates, Irving beat Cooper by a few years! We also have an article “Five Reasons to Teach The Last of the Mohicans,” too.
  2. Many of Irving’s tales are actually re-workings of European legends. At first this might seem like a detriment to Irving: Did he not invent his own stories? The headless horseman from “The Legend of Sleepy Hollow” is based on a Dutch ghost, “Rip Van Winkle” derives from a German folktale, where a man sleeps for twenty years, and “The Devil and Tom Walker” is a re-working of the Faust legend. But Irving’s genius is that while these stories do have European origins, Irving transposed them to America—giving them American settings, an American style, and American themes. America was so young that it had no folklore of its own until Irving singlehandedly created it.
  3. “The Legend of Sleepy Hollow” has universal appeal. Who hasn’t heard of this story in one form or another? Films, television series, and even Disney cartoons reference this story, so it is interesting for almost everyone to read the original story. Not only is the story hilarious, but it teaches the concept of ambiguity. I love the story for its clever ending: Irving leaves it up to the reader to decide what truly happened to Ichabod Crane. Just like a good ghost story, it’s up to the hearer to decide what is true and what is not.
  4. “Rip Van Winkle” teaches an important lesson about what it means to be an American. Most people know the plot of “Rip Van Winkle,” yet very few remember the point of the story. Yes, Rip falls into an enchanted sleep for twenty years, but the kicker is that he sleeps through the American Revolution. When Rip (who is about as un-American as they come) wakes up in a new republic, he pines for the colonies. He misses King George and cares nothing about governing himself. Irving is making a scathing comment on those Americans who are blasé about their freedoms.
  5. “The Devil and Tom Walker” teaches the dangers of greed. The Legend of Faust has been around for ages, so the idea of a mortal making a deal with the devil is a storytelling cliché. But Irving manages to put a unique spin on the old story by giving it American flair. Tom Walker is the perfect ally for the Devil because it suits his nature anyway. He becomes a ruthless moneylender and enjoys every minute of it. But in the end, he must pay with his soul. Although Irving’s version of the story is hilarious, the theme of insatiable greed still comes through loud and clear.

Bonus Reason:  The New York Knicks:  Diedrich Knickerbocker, a faux historian developed by Irving, served as the inspiration for the basketball team’s name.

If you are interested in teaching the stories of Washington Irving, Readers Theater script-story versions are available in our digital textbook Searching for America: Forming a Nation.

By the way my wife and I were able to visit Tarrytown, NY, when we attending one of my student's graduation from West Point. It was a fun, little lit. trip! We saw the Headless Horseman Bridge, Washington Irving's grave, and a cool Headless Horseman chasing Ichabod Crane statue. Pictures are below!


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  • Zak on

    Very cool! I didn’t know that! Thanks for sharing.

  • dan on

    very cool. Irving also lived in the area of Spain that I’m in, and wrote his “Tales of the Alhambra” here. In fact, the hotel across from the Alhambra is the “Washington Irving Hotel” and he was responsible for helping start the movement to restore the buildings.


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