Winged monkeys (often referred to in adaptations and popular culture as flying monkeys) are fictional characters created by American author L. Frank Baum in his classic children's novel The Wonderful Wizard of Oz (1900). The winged monkeys are exactly what the name implies: jungle monkeys with powerful bird-like feathered wings attached to their shoulders which allow them to fly. They are most notable from the famous 1939 musical movie by MGM. Ever since, they have taken their own place in popular culture, regularly referenced in comedic or ironic situations as a source of evil or fear.
The winged monkeys started out as free creatures living in the jungles within the Land of Oz. They were a rather carefree bunch, and also very mischievous by nature. One day the King of the winged monkeys, as a prank, tossed a richly dressed man into a deep river, ruining his handsome costume of velvet. The man, whose name was Quelala, was good natured enough and did not mind the prank. But his fiancée Princess Gayelette, was ever so furious because the day the winged monkeys played the prank, was the same day of Quelala and Gayelette's royal wedding. She had ruled Oz's northern quadrant, called the Gillikin Country, and lived in a small palace made of rubies. Princess Gayelette had also practiced real magic and was a sorceress in her own right. As punishment for the winged monkey's prank, she cursed them by making them all the eternal slaves to the Golden Cap she had originally prepared as a wedding present for her beloved betrothed. The cap itself was a very nice one indeed, studded with real sparkling diamonds, and precious blood red rubies that ran entirely around its 24/karat solid gold brim. The curse of the cap allows its possessor to command the winged monkeys exactly three times whenever they speak the cap's magic incantation aloud. Whenever the words were spoken, the winged monkeys had to immediately stop whatever they were doing at that time, and assist their master at once. The curse of the cap is also rumored to have cost Gayelette half her powers to construct.
Quelala used the Golden Cap only once, commanding the winged monkeys to stay away from Gayelette and her kingdom. The winged monkeys did as they told and disappeared for a very long time. Eventually, the cap somehow fell into the hands of the Wicked Witch of the West, who used the cap's charm to compel the winged monkeys and help her to conquer Oz's western quadrant, the Winkie Country and enslave the native Winkies. Next the Wicked Witch used the cap to drive the Wizard of Oz out of her territory when he attempted to overthrow her. Finally, she uses the cap to capture Dorothy Gale and the Cowardly Lion, and telling the winged monkeys to dismember and destroy the Scarecrow and Tin Woodman in the process.