From the Bookshelf: The Legend of Sleepy Hollow


Ichabod pursued by The Headless Horseman by F.O.C. Darley (1849)

I haven’t taught 11th grade English in about five years, but when I did I remember that I tried my best to follow American literature chronologically, intertwining it with American history (occasionally combining my class with another teacher’s American history class for a few days), because there is something about the literature of our country and our culture that follows along pretty well with our history.

Luckily, doing so meant that by the middle to the end of October, I was usually somewhere in the early 1800s, which meant that if I had wanted to do something seasonal, I had at least a few writers to choose from. Edgar Allan Poe seemed to be the go-to choice, but I usually avoided him because by the time my students had me for a teacher, they had read so much Poe in middle and the early part of high school that he was a bit over-exposed. Besides, one of my favorite stories for Halloween has always been Washington Irving’s “The Legend of Sleepy Hollow.”

This isn’t much of a surprise when you consider that I, along with quite a number of people from my generation grew up watching Disney’s cartoon version of the story of Ichabod Crane and the Headless Horesman on VHS (Disney has always been excellent when it comes to home video–when the first video stores in my town opened up in the early 1980s, the kids’ section was full of Disney tapes and we were constantly taking them out. I got more exposure to literary classics through Disney as a kid than just about anyone). I think that when I first attempted to teach “The Legend of Sleepy Hollow,” I had made the assumption that a number of my students had had a similar experience and might want to read the original material. After all, Washington Irving is one of those American literary figures that you simply cannot skip over if you’re covering the history of American literature.

I mean, this may sound ignorant or off-base or something, but I’d put him right up there with Poe or even Hawthorne (whose “The Birth-Mark” and “Rappaccini’s Daughter” are two of my favorite short stories as well). Unfortunately, things didn’t go as well as I expected. I remember struggling to figure out why, after one day of working on the story, my class seemed pretty lost and frustrated. So I did what I usually do in this situation–asked them why they didn’t seem to like it. “It’s boring,” was the general response.

Now, normally hearing a student say “This is boring” is something you’d kind of blow off. Of course it’s boring to them because that’s what they say about 99.9% of the stuff they do in school. But seeing that was the majority of the class’s opinion, I took another look at what we’d been reading and considered why they might be bored. It turned out they were sort of right. I skimmed the story over again and while I didn’t particularly find it boring, I saw how Irving’s style is dry at times and how there is a bit of a “language barrier” between an early 19th Century Upstate New York writer and an early 21st Century Virginia teenager.

So first, I flogged myself physically and mentally for not being an innovative educator and when the powers that be gave me permission to resume my duties, I basically sped up our study by skipping to the end and walking through the Headless Horseman scene with them before going on to whatever we were doing next (it was probably Emerson or Thoreau, IIRC). I then started to wonder why we felt the need to teach Early 19th Century American literature if the kids were going to start feeling such a disconnect from it. After all, we should be connecting with them and getting them emotionally invested and old texts are antiquated and … well, Twilight. But then I came to my senses and realized that no, just because they found it boring doesn’t mean it’s not worth teaching. It’s just a matter of changing my approach. I kept “The Legend of Sleepy Hollow” in my planning binder for next year.

Unfortunately “next year” didn’t come because I changed schools and as a result changed grades altogether and have been teaching sophomores ever since (with a couple of years of teaching seniors). But when I do approach older texts that have a “language barrier” or sorts or have a structure that tends to be much longer on exposition than your average Michael Bay movie, I think of what value the text has and then how to get them to see that value. “The Legend of Sleepy Hollow” is definitely valuable. It does not have the scariness of a modern “horror” story but Irving definitely does what he can to make it creepy.

He has a monster, he has an urban legend, and he even has a couple of characters–the wimpy guy versus the overbearing bully–that are still common it today’s stories. Ichabod Crane is awkward and Brom Bones, who competes with him for the attention of Katrina Van Tassel, is bombastic and pompous, and his stories of the Headless Horseman certainly put the idea of this scary Hessian ghost soldier by a bridge that results in a pretty chilling scene that in rereading it last Wednesday, found pretty suspenseful. Plus, as “boring” as students may find Irving, I enjoy his attention to detail in setting his scene as well as his attempt to give the people of his time some “historical fiction” in a sense.

There are layers to the story that you can very well uncover, such as historical context, characterization, and theme, that are valuable beyond its simple entertainment value. But if you are looking for Washington Irving in a more entertaining and informative context, check out a 2007 episode of “The Bowery Boys: New York City History Podcast”.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s