The legend of Rip van Winkle comes from a short story by American author Washington Irving, and chronicles the adventures of a Dutch American settler of that name.
The game being played was nine pins, similar to bowling. The legend, and the game, date back to the time of the U. S. Revolutionary War.
The piano playing mover bears a passing resemblance to popular entertainer of the time, Hoagy Carmichael.
The ending scene of a ship being sunk happened just 8 months before Pearl Harbor, an eerie coincidence. Future wartime cartoons would be very patriotic and supportive of America's war efforts.
The inference is that Rip van Winkle didn't pay his rent for two decades because he'd been asleep the entire time.