The Legend of Sleepy Hollow Essay Questions

Explain the importance of the epigraph to “The Legend of Sleepy Hollow.”

The epigraph is from something called “The Castle of Indolence,” which is essentially a description of a land where one is always halfway in a day-dream. These lines clearly emphasize the power of imagination in the story. It is in his powerful imagination that Ichabod finds much of his happiness and excitement in life; indeed, he spends almost all of his time daydreaming, and this allows him to escape from the more mundane aspects of his daily life. It becomes dangerous, however, when he fails to distinguish clearly between his imagination and reality, thus sacrificing his hopes because of his inability to act appropriately to achieve them.

Is the narrator of “The Legend of Sleepy Hollow” reliable?

Diedrich Knickerbocker is a rather unreliable narrator, not because of character flaws but because, as he makes clear in the postscript, he has heard this story from someone else, who did not really believe the story himself. Knickerbocker saves this disclaimer for the postscript, apparently preferring that readers take the story as largely true in order to enjoy it, even though careful readers will be on guard from the beginning, for this is a ghost story. In addition, there are scenes about which Knickerbocker simply could not know the details unless the story had been originally told by Ichabod himself, which is possible, but the provenance of the different elements of the story is not made clear enough to satisfy a historian. A good historian would make efforts to determine which elements are probable before publishing a history he has heard from someone else. But this is not really the point; the reliability of the narrator is not very important because the point is to enjoy a good tale and maybe learn something from the way it is presented.

What do the passages concerning Katrina show about how she (or women in general) are perceived and treated in the town?

The first description of Katrina makes her a commodity, like a food to be consumed: she is “plump as a partridge” and “ripe and melting and rosy cheeked as one of her father’s peaches.” Indeed, she is part and parcel of her father’s farm, not only in Ichabod’s eyes but probably in the eyes of all her suitors. She is described solely in terms of constituents of the farm and in relation to them. Nevertheless, she is a human: a coquette who, like many an 18-year-old, is a mix of contradictions and uncertainties, making it very hard for a suitor to keep up. The narrator does not give her a pass because of her age, however, complaining that she is like the other coquettes who need to be conquered with heroic resolve. Finally, however, Katrina asserts her power of feminine choice; she is the one, it seems, who rejects Ichabod's suit and accepts that of Brom Bones.

Discuss how Ichabod’s powerful imagination leads to his downfall.

Ichabod’s imagination leads to his downfall in two ways. First, his imagination leads him to get completely carried away about the situation with Katrina, such that he thinks his chances are much better than they are, and he fantasizes about the future so much that he cannot imagine failing--but this also keeps him from making the necessary life changes to become the kind of person suitable for her. Second, his great enjoyment of ghost stories and other supernatural tales, which he actually believes because of his strong imagination, makes him utterly susceptible to Brom Bones’s prank, so he is doubly defeated.

Why is it significant that this story is set in America rather than Europe?

Ichabod’s ability to livee in a dream world that almost overpowers his reality seems specifically suited to America. America is a land of ideas and freedom to succeed or fail on one's own merit and initiative. Within the rigid class systems of Europe, in contrast, a talented and ambitious man finds it difficult to rise above his birth, so an untalented and un-ambitious man would not even bother to dream about possible success, or if he did, he would be certain of its practical impossibility. In America, no glass ceiling can keep Ichabod down. Even though he is still an outsider in the town, this town is unusual for being so close-knit, and America offers vast resources and freedom of movement so that he could succeed somewhere else. It is mainly his own indolence in his main work, not the failure of the townspeople to appreciate his gifts, that holds him back. Instead of telling and listening to ghost stories, he could have taken entrepreneurial steps to succeed in business, which is the way Americans tend to find financial success. Even so, America is free enough for the intellectual or even the pseudo-intellectual (with some side talents like singing) to eke out an existence.

How are readers likely to feel about the fact that Brom marries Katrina, even though Ichabod is the protagonist?

Although Ichabod is the protagonist of the story, he is more of an anti-hero who does not seem to deserve marriage to Katrina. That he fails is a kind of poetic justice to punish him for his selfishness. Brom seems somewhat more genuine than Ichabod in his attempts to win Katrina’s hand, for he is willing to fight tooth and nail to defeat his rival, while for Ichabod it is more of a scheme. Ichabod’s passivity and his blatant fantasizing about Katrina’s money (but not about her) make us think that, coquette or not, Katrina can do better. Brom is more a man of the people, so readers are more likely to be glad that Katrina has chosen him. At the same time, we do not know her very well, so it is hard to know how well this match is going to turn out.

How can Ichabod be said to be a parallel to Crayon?

Both Crayon and Ichabod have intensely overpowering imaginations, to the extent that they border on hallucination. Both figures also use their powerful imaginations as a method of escape--from daily life, perhaps, or from the truth. Ichabod uses his imagination to make his life more exciting and more fulfilled than it is, while Crayon uses his imagination to make his travels seem more significant and enjoyable. In both cases, the fiction is often better than the truth, and both of these characters have the imaginative capacity to choose their fiction and believe it.

What do ghosts and ghost stories represent metaphorically in this tale?

Ghosts and ghost stories, according to the narrator, only exist in America in the oldest villages, which have been settled for many generations, and which are relatively unchanging. This is because America is too young to have too many ghosts yet, but also because, as Knickerbocker believes, the ghosts do not want to come out in a town where they no longer know anyone. This shows that "ghosts" can stand for any kind of connection between the living and the dead, the past and the present, like rituals, customs, and traditions, which tie parts of the past and those who have died together with the present and the future. Ghost stories, like any community's folklore, help the community understand itself and its history.

“The Legend of Sleepy Hollow” is often read on its own, but it was originally published as part of The Sketchbook of Geoffrey Crayon, Gent. How does the story fit into the rest of The Sketchbook? What themes from the book does it complicate, or what themes complicate it?

A major theme in The Sketchbook is the strength of the imagination and whether it should be allowed to overpower reality. It is rarely a dangerous event in the other stories of The Sketchbook, but “The Legend of Sleepy Hollow” shows what the dangers can be, in the example of the overly-imaginative, indolent Ichabod Crane. This complicates what appears to be Crayon’s verdict throughout the rest of Irving's book—that it is not necessary to pick reality if you can imagine something better. By 1820, writers had generally turned the corner from classical to romantic themes, and questions about what to do about the imagination were of significant interest.

What is the importance of the “Postscript”?

The “Postscript” introduces a new level of uncertainty about the reliability of the story. At the same time, it challenges the reader to believe the story anyway. In admitting that Knickerbocker did not find this story himself, and that even the man who told it to him only half believed it, he is distancing us further from the tale. But the image of the unpleasant man who does not enjoy the story because he doesn’t believe it is a strong lesson for those who are too curmudgeonly or jaded to enjoy a good story.