What is humorous and ironic within the story of The Legend of Sleepy Hollow by Washington Irving?

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"The Legend of Sleepy Hollow" has several points and components that give the story a great deal of humor and irony. For one, Ichabod Crane is not at all a typical romantic hero. He is awkward, nervous, superstitious, and somewhat unattractive. Furthermore, he only cares to marry Katrina for the social capital that he stands to gain from the arrangement. Indeed, Crane in fact represents the classic archetype of a romantic villain. In a more traditional story, the action would almost certainly be told from the perspective of Bones, who, even as the story's antagonist, more readily fits the archetype of romantic hero.

Another point of irony in the story is the ending. It is implied that Bones was the horseman all along, meaning that Crane was in no way absconded by spirits. More than likely, he simply fled Sleepy Hollow forever. It is, however, ironic and humorous that such a superstitious man constantly vexed by horror stories ends up becoming the subject of one.

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The humor and irony in the story emerge from the way Ichabod Crane is tricked and outwitted by Brom Bones.

The irony is that Ichabod Crane is the scholar. He is the smart one. He comes to Sleepy Hollow to be the school teacher and is well steeped in folklore, legend, and book learning. He is the one the reader might expect to outwit Brom, not vice versa.

Both Crane and Brom Bones want to marry Katrina. Brom is popular, strong, and has no pretension to higher knowledge. He loves Katrina for herself, not her property, unlike Crane.

Ironically, however, it is Brom who figures out how to best his rival and run him out of town. He knows that Crane is superstitious, so he sets up a "headless horseman" to frighten him away. When the nervous Crane sees the horseman, he believes it is a supernatural being and is frightened from the village.

Irving shows the full-blooded, practical, down-to-earth American male besting the high-strung scholar in a battle of wits. We are encouraged to laugh at the foolish Crane for being so easily deceived.

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