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Flying monkeys, as illustrated by W. W. Denslow in The Wonderful Wizard of Oz

Winged Monkeys (often referred to as flying monkeys) are characters from The Wizard of Oz, of enough impact between the books and the 1939 movie to have taken their own place in pop 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. They were controlled by a golden hat, initially worn by the Wicked Witch of the West who used it to set the monkeys upon Dorothy and her friends. At one point they destroy the Scarecrow entirely, leaving him scattered across the landscape.

An account in the The Wonderful Wizard of Oz explained that the hat been made and imbued with power by a princess named Gayelette. When she was to marry a man named Quelala, the monkeys played a prank on him. Angry, she made the cap, and gave it to Quelala as a wedding present. Quelala merely ordered the monkeys to no longer play pranks, but after he died, the cap fell into the hands of the Wicked Witch. After her death, Dorothy used the cap three times, and finally gave it to Glinda, who ordered the monkeys to carry Dorothy's companions back to their homes in Oz, and then to cease to bother people, and then gave them the cap as their own, to free them.^[1]

In Gregory Maguire's revisionist novels Wicked: The Life and Times of the Wicked Witch of the West and Son of a Witch, the flying monkeys were created by Elphaba (the Witch) as part of her experiments on the nature of the soul and what distinguishes non-speaking animals from intelligent, speaking Animals. In these novels, most of the flying monkeys cannot speak, but Elphaba's favorite (named Chistery) has a distinctive speech pattern characterized by the repetition of similar-sounding words. In the musical adaptation, the monkeys gain wings as part of a magic spell gone awry.

The Vertigo comic book series Fables features a flying monkey named Bufkin, who may be a survivor of a conquered Land of Oz.

Main article: Political interpretations of The Wonderful Wizard of Oz

Some historians who interpret The Wizard of Oz as a political allegory suggest the Winged Monkeys represent African-Americans, oppressed by an overbearing force and who are relieved to be free of that bondage when the evil force is terminated. Others see them as hired Pinkerton Agents who worked for the Trusts in the 1890s and hounded labor unions. (L. Frank Baum made an explicit reference to Pinkerton agents in a later book, "Lost Princess of Oz," p 211)

1885 Puck cartoon shows President Cleveland as Lion, and shows other politicians as chattering (flying?) monkeys. Cleveland has captured and is killing one monkey.

• Flying monkeys have appeared in Buffy the Vampire Slayer, and The Simpsons.
• The Wayne's World catch-phrase "and monkeys might fly out of my butt!" may be a reference, at least incidentally, to the winged monkeys.
• In the movie Jumanji, monkeys see inside a TV shop on a television the winged monkeys from the Wizard of Oz, so they break inside the shop and steal TV sets.
• In the 1973 movie Hunter, actual footage from the Wizard of Oz movie is used to brainwash a race-car driver, terrorizing him until he screamed the line "Stop the monkeys! PLEASE Stop the monkeys!"
• In Todd McFarlane's action figure line "The Twisted Land of Oz," two flying monkey action figures (with a bloated Munchkin) are available as part of the "Collector's Club." According to the accompanying story, they are the Wizard's minions, transformed into steampunk cyborgs due to "Ozmic power."
• The music video for "Heretics & Killers" by Protest The Hero opens with a shot of the front page of a newspaper stating 'The Witch is Dead: Flying Monkeys Out of Work'. The remainder of the video features the bandmembers dressed as the Flying Monkeys, trying (and failing) at various jobs, begging on the street, getting thrown out of a bar, and rocking out.
• In the DCOM movie Halloweentown High Debbie Reynolds' character Aggie Cromwell say "Whoever heard of hockey without Flying Monkeys".