1577. Winged Monkey

Winged monkeys (often referred to in adaptations and popular culture as flying monkeys) are characters from The Wonderful Wizard of Oz, of enough impact between the books and the 1939 movie to have taken their own place in popular culture, regularly referenced in comedic or ironic situations as a source of evil or fear.

In the original Oz novels, these were just what the name implies: intelligent monkeys with wings. The Winged Monkeys were once a free people, living in the forests of Oz. They were carefree, but rather mischievous. One day the King of the Winged Monkeys, as a prank, tossed a richly dressed man into a river, ruining his costume of silk and velvet. The man, whose name was Quelala, was good natured enough, but his fiancée, a sorceress named Gayelette was furious, and punished the Winged Monkeys by making them the slaves to the Golden Cap she had prepared as a wedding present for her betrothed. The cap allows its possessor to command the winged monkeys three times.
Quelala used the Golden Cap only once, commanding the Winged Monkeys to stay away from Gayelette. Eventually the cap fell into the hands of the Wicked Witch of the West, who used the Winged Monkeys to conquer the Winkie Country, defeat the Great Oz, and capture Dorothy and the Cowardly Lion, destroying the Scarecrow and Tin Woodman in the process.
After the witch was melted, Dorothy took the cap and used it. The first time, she commanded the Winged Monkeys to carry her and her companions to the Emerald City. Then she asked them to carry her home to Kansas, but they could not, thus resulting in her wasting the cap's charm. Her third request was to carry her and her friends over the mountain of the Hammer-Heads.
Dorothy finally gave the cap to Glinda, who ordered the monkeys to carry Dorothy's companions back to their homes in Oz, and then to cease to bother people. She then gave them the cap as their own, to free them.