•Why it earns a slot
Irving's story gave American literature one of its most durable archetypes, using the device of enchanted sleep to dramatize the disorientation of a new republic breaking from its colonial past, while the image of a man who slept through a revolution remains a precise and widely cited metaphor for political obliviousness.
Rip Van Winkle, a good-natured but idle Dutch-American villager in the Catskill Mountains, escapes his nagging wife by wandering into the hills, where he drinks a mysterious liquor with a ghostly crew and falls into a sleep that lasts twenty years. He wakes to find his wife dead, his friends gone or changed, his country transformed from a British colony into the United States, and himself a bewildered relic of a vanished era. Taken in by his now-grown daughter, Rip happily resumes his idle life, freed at last from matrimonial tyranny, and spends his remaining years telling his story to anyone who will listen.
This distillation is written from the freely available original, which is always the better read when you have the time: gutenberg.org.