Study Guide

The Legend of Sleepy Hollow Themes

  • Greed and Gluttony

    If you could describe Ichabod in one word, what would it be? Ugly as all get out? Oh wait, that's five words. Let's try again, and we'll be less superficial this time. How about greedy? This guy wants everything—the girl, the bling, the pancakes—and his green eyes don't hide it. Irving really works his humorous chops in "The Legend of Sleepy Hollow," turning Ichabod's greed into an exaggerated bundle of absurdity. But our author does stick to one common convention (sorry, Gekko): greed is not good.

    Questions About Greed and Gluttony

    1. Why do you think Irving chose greed to be one of Ichabod's strongest character traits? Why not sloth or lust or some other fun deadly sin?
    2. Is anyone else in the story greedy, or does Ichabod stand out in a town full of decent people? 
    3. How would the story change if Ichabod got the girl? What would that say about greed?
    4. Wait a second, greed? Isn't it more just gluttony? What do you think—is Ichabod in it just for the food, or does he want the wealth and power, too?

    Chew on This

    Ichabod's eyes are too big for his stomach. When the Headless Horseman attacks him, it serves him right.

    Ichabod isn't the only greedy one around these parts. Katrina is greedy for power over guys' hearts.

  • The Supernatural

    Boo! Gotcha! Okay sure, the supernatural can be scary, but isn't there more to it? Are there different types? Can it be funny? Is it real or is it total fluff? And most importantly, was it Brom or the Headless Horseman? We know that's a lot of questions, but "The Legend of Sleepy Hollow" seems like an investigative report about all things supernatural. We end up with more questions than answers, but one thing's for sure in our sleepy little town: whatever it is, the supernatural is going to come for you. So put up your dukes.

    Questions About The Supernatural

    1. Is there a difference between the stories the wives tell and the stories Ichabod tells? If so, spill the beans: what's so different?
    2. How do science, reason, and the supernatural interact in "Sleepy Hollow"? Which concept normally takes the cake? Are there any exceptions?
    3. Writer and scientist Arthur Clarke once said, "Any sufficiently advanced technology is indistinguishable from magic." Is this true in "Sleepy Hollow"? How about when Ichabod talks about astronomy like it's magic? 

    Chew on This

    It doesn't matter if the supernatural is real in "Sleepy Hollow"; it still has power over people, and that's all that counts.

    This isn't a story about the supernatural. After all, the whole thing is totally made up.

  • Wealth

    A lot of "Sleepy Hollow" is kind of like a 19th-century episode of Cribs. We get a pretty good idea of what Baltus's pad looks like, and—well, it's pretty awesome. But just like with everything else in the story, Irving calls into question what being rich really means. Can Baltus really be rich if he doesn't live in a marble-floored mansion with mountains of gold and silver? Or is being wealthy just having more than enough to get by? Wealth separates the hungry and skinny (Ichabod) from the full and fat (Baltus), but can anyone really go hungry when trees are overflowing with fruits? Irving leaves those questions for you to figure out.

    Questions About Wealth

    1. What makes someone wealthy in "The Legend of Sleepy Hollow"? Is anyone really poor? Why or why not?
    2. Imagine Baltus is a rich old man today. What might his home look like? Does wealth mean something different today than it did in the 19th century?
    3. Irving sure does talk about the bounty of nature a lot. What do all of these images of apples, corn, and other natural goods really mean?

    Chew on This

    With "Sleepy Hollow," Irving is making fun of what it means to be "rich" in America as compared to Europe.

    Wealth is deeply connected with nature in "Sleepy Hollow."

  • Man and the Natural World

    In "The Legend of Sleepy Hollow," the relationship between man and nature is way more convincing than the one between Katrina and Ichabod. Nature is like another character here, and man is it chatty. Birds have parties, there are squadrons of farm animals, and like any good friend, nature is sympathetic when you're sad. Ichabod seems oblivious to his relationship to nature, except that it gives him things to eat. But the other residents of Sleepy Hollow seem to be best buds with the land around them, forming an interdependent relationship that lets them live quietly and comfortably.

    Questions About Man and the Natural World

    1. Are the natural and the supernatural mutually exclusive In "Sleepy Hollow"? Where do people come into play in this equation?
    2. What is the relationship between man and animals in "Sleepy Hollow"? Why do you think Irving wrote about them this way?
    3. When the now-U.S. was settled, it was considered a land with plenty of natural resources. Irving wrote "Sleepy Hollow" not too long after the American Revolution and his trip to Europe. Do you think this affected his writing? How?

    Chew on This

    In "Sleepy Hollow," man's relationship with the natural world is simply to dominate it.

    Nature and mankind have an interdependent relationship in "Sleepy Hollow"—each one rubs off on the other.

  • Warfare

    Love is a battlefield. But so is the classroom. Oh, and so is the actual battlefield. War is everywhere in this story, which makes sense given that it was written not too long after the American Revolution. But we guess literal wars were too boring for Irving, because they definitely take the back seat to the battlefield of love. Throughout "The Legend of Sleepy Hollow," the image of knightly combat is used to explain the difficulty of getting the girl. Although we're pretty sure Irving's knights wouldn't exactly fit in at the round table.

    Questions About Warfare

    1. There's no actual warfare in "Sleepy Hollow," so what's up with all the war and knight imagery?
    2. What would this story be like if the war references were replaced with romance? Would it seem more familiar to you?
    3. Imagine "Sleepy Hollow" took place today. How might the images we know of modern warfare change the tone of the story?
    4. Is there a chivalrous knight in Sleepy Hollow? How about a terrifying dragon? (We're not talking literally here, by the way—unless we totally missed something…)

    Chew on This

    Telling stories about the war is a badge of honor for the older residents of Sleepy Hollow.

    Love isn't about romance; it's about winning the battle. Whoever gets the girl wins.

  • Truth

    We're not in Kansas anymore, Shmoopers. Dreams, apparitions, specters—Sleepy Hollow has them all. But here's the question: are they real? Well, that's a question the Sleepy Hollowers have some difficulty untangling—something's definitely in the water there. And as readers of "The Legend of Sleepy Hollow," we don't have it easy, either. Thanks to our super unreliable narrator, we have to second-guess nearly every word in the story. Is there any sincerity? What's real and what's not? And most importantly, does it matter?

    Questions About Truth

    1. Do you trust the narrator? Why or why not? And if not, why do you think Irving made him so untrustworthy?
    2. Who gets to decide what truth is in "Sleepy Hollow"?
    3. How would the story change if we knew for sure that everything was fake? What if we knew it was all real?

    Chew on This

    Facts are totally overrated in Sleepy Hollow; these people only care about what's interesting.

    The postscript tells us that it doesn't matter if something is true or not, what matters is that it's funny.

  • Appearances

    Irving spends so much time describing the characters in "The Legend of Sleepy Hollow" that you'd probably recognize them if you passed them on the street. (Can the same be said for your other favorite literary characters?) But looks aren't only skin deep in this story; they actually define who you are. Got green eyes? Then you're probably greedy. Got big muscles? You're a jock. Why not develop the characters further? Well, you already know all you need to know about them.

    Questions About Appearances

    1. Is there anyone who doesn't get an elaborate physical description in "Sleepy Hollow"? Who is it? Why do you think they aren't described? And while you're at it, make up your own description.
    2. Why do you think that Irving focused so much on the appearances of his characters?
    3. Imagine we had no idea what Ichabod looked like. How else could Irving describe him to show us how awkward he is?

    Chew on This

    What you see is what you get with the characters in "Sleepy Hollow."

    Ichabod's appearance doesn't really matter. He'd still be the same greedy, gluttonous guy even if he were a stud.