What is humorous and ironic in "The Legend of Sleepy Hollow"?

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.

What instances of satire are in "The Legend of Sleepy Hollow"?

In "The Legend of Sleepy Hollow," Washington Irving satirizes or makes fun of the effete, European-style intellectualism of schoolmaster Ichabod Crane. Crane lives in the folktales and legends of the past. He is not a "manly" man and does not get along well with other men, surrounding himself with a cadre of women who are impressed with his knowledge. The key point about Crane's book learning is that it has not given him common sense or made him a good person. He wants to marry Katrina for the wrong reason, which is to get his hands on her wealth. Also, for all his erudition, he is outwitted and scared off by the uneducated ox of a young man, Brom.

In satirizing Crane, Irving contributes to creating the mythos of the superiority of the practical, down-to-earth American way in contrast to the over-educated, backward looking European mindset.

What instances of satire are in "The Legend of Sleepy Hollow"?

In "The Legend of Sleepy Hollow," Irving uses satire to mock both Ichabod and Katrina as well as Ichabod's courtship of her.

Katrina is a flirt: she only wants Ichabod to make her love interest, Brom, jealous. On the other hand, Ichabod is more interested in her lands and inheritance than Katrina herself. Irving mocks the entire man-woman relationship making Ichabod seem greedy for land, and Katrina more than a bit shallow. "She was withal a little of a coquette" (p.10). Both characters are made to appear ridiculous in their relationship. In fact, Ichabod was "peculiarly happy in the smiles of all the country damsels" (7). If not for her father's land, Katrina would have been little different from the other women.

As the satire progresses, Ichabod literally falls in love with the house he imagines will be his one day: "When he entered the house, the conquest of his heart was complete" (p.12). He is attracted to the house, not Katrina.

Furthermore, Irving likens Ichabod to a knight having to fight dragons to win his lady (p.13); unfortunately, Ichabod is unfit for that role. He merely has to win Katrina from Brom which is a more impossible feat. In this way the courtship between the two is presented as ridiculous. Ichabod cannot measure up to Brom nor is Katrina even interested in him. Both Katrina and Ichabod have their own agendas, neither motive is love.

What instances of satire are in "The Legend of Sleepy Hollow"?

This is obviously a story about stories and storytelling and the limits of the imagination, and Irving carefully constructs his satire to focus on the dangers of believing in stories too much and trangressing the boundaries between fiction and non-fiction. He chiefly does this through the character of Ichabod Crane, who is presented as a man who does not understand the limits of imagination. He is obsessed by his dreams of marrying Katrina Van Tassel:

...soft anticipation stole over his mind of dainty slapjacks, well buttered and garnished with honey or treacle, by the delicate little dimpled hand of Katrina Van Tassel.

However he is unable to live up to those dreams and is genuinely shocked by Katrina's refusal. His lack of discernment is key in the way that Brom is able to trick him, because he is unable to identify that the legend is just that: a story. This is of course linked to the postscript of this tale, when the wise storyteller is very clear about his perception of fiction and reality:

"Faith, sir," replied the storyteller, "as to that matter, I don't believe one half of it myself."

Thus the target of this satire is our own tendency to blur the boundaries between stories and reality, and the way that we leave ourselves exposed when we do so, just as Ichabod Crane did. We must heed the message of this story and never let our imaginations get the better of us.

What is the subject of Washington Irving's satire in "The Legend of Sleepy Hollow"?

 Washington Irving's "Legend of Sleep Hollow" satirizes, the supposedly, refined culture of city folks through the character, Ichabod Crane.  Ichabod Crane comes from Connecticut as a refined and educated man in search of a teaching position in the village of Sleepy Hollow; however, he is unaware that the town is "given to all kinds of marvellous beliefs; are subject to trances and visions; and frequently see strange sights, and hear music and voices in the air."  Right here, conflict between city and rural life is aired to the reader: the mood of the village atmosphere is set which will, eventually, contribute to Crane's downfall.  Though educated, Ichabod is a true believer of the supernatural and is supersititious because he " was a perfect master of Cotton Mather’s history of New England Witchcraft, in which, by the way, he most firmly and potently believed."   By mentioning this, Irving points out Crane's flaws:  too much knowledge can lead to false logic and misbelief.    

Though various folktales and legends have been told through the generations of the village, they are considered to be only heresay.  Unfortunately, outsiders, like Crane take them to heart.   During the annual Van Tassel gathering, folks got together and shared stories:  

"All these tales, told in that drowsy undertone with which men talk in the dark, the countenances of the listeners only now and then receiving a casual gleam from the glare of a pipe, sank deep in the mind of Ichabod."   

Here, the gullibility of the educated city man is shown despite these stories being what they are:  stories.   

Though it's the headless horseman that goes after Crane, his demise occurs because of his true belief of these stories:   

 "All the stories of ghosts and goblins that he had heard in the afternoon, now came crowding upon his recollection. The night grew darker and darker; the stars seemed to sink deeper in the sky, and driving clouds occasionally hid them from his sight. He had never felt so lonely and dismal."   

Irving points out how false belief contributes to logic and forces uneasiness upon the individual. From the start of the story, Irving makes clear of the division of the city outsider to that of the rural country folks by the inclusion of Ichabod's character.  Since his arrival, he had been marked, as seen by the numerous pranks played on him by Brom and the boys.   The belief of the legends and folks tales further establishes how the city folk can create realistic supernaturalism despite really being heresay.   On a side note, Irving's influence for this story comes from German folklore which may suggest the division of Europeans and Americans as seen by the mistreatment of Ichabod's character.