The winged monkeys started out as free creatures living in the jungles in the Land of Oz. They were a rather carefree but mischievous bunch, until their king, as a prank, tossed a richly dressed man into a deep river, ruining his velvet costume. His fiancée, Princess Gayelette, was furious since this was their wedding day. She had ruled Oz’s northern quadrant, Gillikin Country, and was a sorceress; as punishment for the prank, she enslaved them and made them obey the Golden Cap. Any wearer of the cap could make three demands of the monkeys. Later, this cap fell into the hands of the Wicked Witch of the West, who used it to make the monkeys help her in conquering Oz’s western quadrant (the Winkie Country), enslave the native Winkies, and drive the Wizard of Oz out of her territory when he attempted to overthrow her. After Dorothy Gale kills the Wicked Witch, she put on the cap, unaware of its power, and when she learns its power she uses it to make the winged monkeys carry her and her companions to the Emerald City. Then Dorothy asked them to carry her back to Kansas, but the winged monkeys could not leave the magical realm of Oz; thus the second request was wasted. Dorothy’s third and final request was for them to carry her and her company over the rocky mountains inhabited by the Hammer-Heads, who would not let them pass over their turf.
Dorothy ends up handing the Golden Cap over to Glinda, the beautiful Good Witch of the South. Glinda then ordered the winged monkeys to carry Dorothy’s companions back to their new homes in Oz after Dorothy’s departure, and then to simply cease to bother people and not play pranks on them anymore. She then gave the winged monkeys the cap as their own, breaking the curse and setting them free.