Why Irving's Sleepy Hollow Won't Let Us Go

By Andy — 2026-09-12 — Literary News

I picked up Lopate's essay thinking I'd find a neat literary history. What I found instead was someone asking why we keep coming back to a man who takes a nap for twenty years and wakes up free.

That's the trick of "Rip Van Winkle."

Rip isn't brave. He's not particularly clever. He's henpecked, lazy, he lets his farm rot while his kids run around in rags. The only thing he does well is escape into the woods with his dog. One afternoon, after napping in the forest, he stumbles on some strangely dressed men in old Dutch clothes playing ninepins. They give him liquor. He sleeps. And when he wakes up, twenty years have passed. The American Revolution happened. King George's portrait came down from the tavern and Washington went up in its place. His wife, the "termagant" who tormented him endlessly, is dead.

He is free.

Lopate nails why this matters: an ordinary man, a loser by any honest accounting, becomes immortal in American culture simply because he was asleep through the noise. There's something in that story that speaks to a hunger we don't quite admit we have—the desire to resist being heroic.

It's not subtle.

But then Lopate moves to Ichabod Crane, and here's where Irving's real skill emerges. Ichabod isn't a tragic figure or a moral lesson. He's ridiculous. His nose is snipe-like. He's a schoolmaster courting a wealthy farmer's daughter, Katrina Van Tassel, and when he thinks about marrying her he doesn't imagine romance—he imagines food. Roasting pigs with apples in their mouths. Pigeons in pies. Geese swimming in their own gravy. Irving writes this catalogue of gluttony with the kind of comic precision that Charles Lamb would recognize, building it to absurdity, making it hilarious and uncomfortable at once.

Ichabod has one advantage in love: he's regarded as a gentleman of cultivation, a man of letters. The village girls smile on him. But he's up against Brom Van Brunt—brawny, Herculean—and that's a problem no amount of grooming can fix.

What Lopate understands, and what Irving knew, is that these stories work because they're not really about ghosts or sleeping. They're about storytelling itself. Irving sets up "Sleepy Hollow" by calling it a retreat from the world, a place where you can "dream quietly away the remnant of a troubled life." He mentions the bewitchment, the haunted spots, the local superstitions. He's priming us. He's being a showman.

The prose does most of the work, actually, not quite right—the storyteller's fluency, his controlled irony, the way he pauses to drop in fresh details about how people look or what they want. That's what keeps readers coming back. Not the horror. The company.

There's politics in here too, as Lopate notes. Ambivalence about what America was becoming. The old patriarchs are idle and quiescent. Rip becomes a kind of oral historian, telling the story of the times before the war to anyone who'll listen. But underneath all that, Irving is just doing what a good writer does: he's making you care about people you wouldn't normally notice.

That's why we're still here, nearly two centuries later, in a used bookshop in Thailand, talking about a man from the Hudson Valley who wrote stories about sleepy villages and ridiculous schoolmasters.

Source: "For nearly 200 years, the story has captured the imagination of both children and adults." — Historic Hudson Valley