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Compare Ichabod Crane and Rip Van Winkle in "The Legend of Sleepy Hollow" and "Rip Van Winkle" as images of manliness.

Washington Irving’s Rip Van Winkle and Ichabod Crane are both anti-heroes who lack masculine virtues and heroic qualities.

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Rip Van Winkle and Ichabod Crane are both anti-heroes who lack masculine virtues and heroic qualities. This absence of physical courage is the first thing we are told about Rip Van Winkle:

He was a descendant of the Van Winkles who figured so gallantly in the chivalrous days of Peter...

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Rip Van Winkle and Ichabod Crane are both anti-heroes who lack masculine virtues and heroic qualities. This absence of physical courage is the first thing we are told about Rip Van Winkle:

He was a descendant of the Van Winkles who figured so gallantly in the chivalrous days of Peter Stuyvesant, and accompanied him to the siege of Fort Christina. He inherited, however, but little of the martial character of his ancestors.

The author also describes Rip as “an obedient, henpecked husband” and says that “he was a great favorite among all the goodwives of the village.” The children also love him and he spends a great deal of time with them, playing games and telling stories.

This connects Rip with Ichabod Crane, who is also described as a great favorite with the ladies of Sleepy Hollow. He is evidently not so popular with the boys he teaches, being a rather less amiable character than Rip Van Winkle, and inclined to use the birch to enforce discipline (the very fact that he has to do this so frequently suggests that the boys do not respect him). The essential point, however, is that both Rip and Ichabod spend all their time with women and children rather than with men.

Rip’s defining characteristic is indolence. Ichabod is mainly notable for his cowardice and superstition. Dame Van Winkle has to drive Rip to do his duty and work to support his family. Ichabod’s only hope of becoming wealthy is to marry Katrina Van Tassel and live off the produce of her family’s farm. In terms of industry, courage, enterprise and any kind of heroism, Rip Van Winkle and Ichabod Crane are the very antithesis of the pioneering spirit of manliness which was building up the young Republic in Washington Irving’s time.

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Both Ichabod Crane and Rip Van Winkle run counter to traditional images of masculinity.

Crane is a tall, thin, creepy-looking man with giant feet and a small head. He is likened to a scarecrow and a figure of famine. He works as a schoolmaster and bullies the children with beatings, while he is all softness and kindness to the ladies.

Crane is superstitious and likes to hang with the women, especially to hear stories about local ghosts and witches. This tendency to like the older ladies and old wives' tales shows he has an effeminate side, especially as he is often frightened walking home after these visits.

Crane is contrasted to the very red-blooded, masculine Brom Bones, a muscular, hearty, robust, and charismatic prankster figure who leads a group of young men. Brom represents all the pragmatic masculinity that Crane does not.

Rip Van Winkle also lacks traditional masculinity in his happy-go-lucky, apathetic inability to provide for his family or take care of his farm. Like Crane, though without such a malevolent personality, he likes to help the ladies with small chores. He would rather be drifting around aimlessly, however, or talking over old news in front of the inn, than doing anything purposeful to improve his life.

Both characters represent what a new nation wanted to reject: apathy, superstition, and a backward-looking quality associated with Europeans. Irving is contributing to building the myth of the American character as hardy, pragmatic, resourceful, energetic, and robustly masculine. This is represented by the clever Brom, who outsmarts the nervous Crane and wins Katrina. In "Rip Van Winkle," it is represented by the younger males in the village (not by accident, Rip sleeps through the American Revolution) who are energetically involved in the elections. They are participants in nation-building, unlike the apathetic, Old-World Rip, who was content to let George III rule.

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Your original question had to be edited because it actually contained more than one question. Enotes regulations state that you are only allowed to ask one question, so please remember this in future. I will therefore focus on your first question alone.

Well, if it is images of manliness you are looking for, Ichabod Crane and Rip Van Winkle don't seem to present us with the kind of masculinity and power that we associate with the term. Note how Ichabod Crane is introduced in the introduction to "The Legend of Sleeply Hollow":

The cognomen of Crane was not inapplicable to his person. He was tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame most loosely hung together.

His eccentric appearance coupled with the way that his presence makes people think of famine victims surely does not present him as a red-blooded male in the way that Brom Brones is presented. Certainly, it is not just his appearance that gives us this impression: the ease with which Brom Bones is able to trick Ichabod and scare him away shows that he is a weak-willed coward at best.

In the same way, Rip Van Winkle is presented as a man who is responsible and able to look after his family. The text shows that he is willing to work for anyone except for his own wife and family, and how his family suffer from this neglect as a result. He is shown to be a happy-go-lucky kind of figure who is incapable of asserting himself:

Rip Van Winkle, however, was one of those happy mortals of foolish, well-oiled dispositions who take the world easy, eat white bread or brown, whichever can be got with least thought or trouble, and would rather starve on a penny than work for a pound.

His unwillingness of improving his own position makes his wife and children suffer, and does not present a strong masculine image. In addition, the way in which he allows himself to be dominated by his wife and flees her regularly presents him as a weak, irresponsible man.

Thus it is that both of these characters are not presented in a way that allows us to associate them with traditional images of masculine strength and responsibility.

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