Walking by a storybook-looking neighborhood, Popeye sees that the ever-asleep Rip Van Winkle is being dispossessed and thrown out of his house for failing to pay the rent in over twenty years. Popeye would not leave the elderly, sleeping man on the street so he carries him to his own home, taking his guest to bed, and going to make some tea for when his extended slumber ends.
Van Winkle turns out to be not only a sleeper but a sleep-walker; he gets up without waking and wanders to a nearby forest where a group of magical dwarfs amuse themselves by playing ten-pin bowling. Popeye arrives, looking for Rip, and tries to make the imps quit their noisy game. Two of them attack him, at which Popeye asserts that he will not fight individuals that much smaller than himself. The imps band together and manage to compress his legs and torso, making him as little as they are. Popeye is punched and thrown against the pins but, now being imp-sized, he fights back: he turns the dwarfs themselves into pins then bowls them. The many imps now produce a rain of bowling balls, pins and other objects so Popeye decides to eat his spinach in order to recover his normal size and carry the ever-asleep Rip Van Winkle away.
Back home, Popeye again puts Rip to bed and this time also takes off the old fellow's clothes. However, the sound of a coin falling off a pocket is enough to wake Van Winkle, who cries "a pickpocket!" and begins shooting his blunderbuss at the well-meaning sailor.
- Popeye Meets Rip Van Winkle at the Internet Movie Database