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, winged monkeys were just what the name implies: intelligent monkeys with bird-like 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 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 armies of the Wizard of Oz, and capture Dorothy Gale 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 the Winged Monkeys the cap as their own to free them.
In the classic 1939 film The Wizard of Oz, the monkeys are apparently intelligent enough to obey commands, but do not speak, as in the book. They kidnap Dorothy and dismantle the Scarecrow, but do nothing to the Tin Man or the Cowardly Lion, leaving them free to put the Scarecrow back together and rescue Dorothy. There is no mention of any three wishes in the film, suggesting that the monkeys serve the witch unconditionally. Nikko (the head monkey) is shown again after the Witch orders him to throw a basket containing the dog Toto in the river (an order that Dorothy prevents him from carrying out), with the Witch as she angrily throws down the hour glass after the trio rescues Dorothy, and once more after the Witch has been melted. There is only a brief glimpse of the Golden Cap in the film: after Dorothy and the Lion reawake after Glinda breaks the spell on the poppies conjured by the Witch, she is seen watching them in anger in her crystal ball. Nikko hands her the Golden Cap and she utters the "somebody always helps that girl" line, before throwing the cap across the room angrily. The reason for this brief appearance comes from a scene deleted from the final film. In the script, after the Witch conjures up the poppies that put Dorothy, Toto and the Lion to sleep she orders Nikko to fetch the Golden Cap so she can summon the Winged Monkeys and they can take the Ruby Slippers from the sleeping girl. However, she never gets a chance as the spell is broken before she can. Why the Witch doesn't use the Golden Cap to summon the monkeys when she sends off into the Winkie Forest to capture Dorothy and Toto is unknown. In the film, the cap looks almost identical to the original artwork by Denslow in the book.
They were never included in any of the subsequent Oz books by Baum, although they are mentioned in The Marvelous Land of Oz, and Alexander Volkov's Oz-based series briefly features them once more (and they are also mentioned once more).
- In the film version of The Wiz, the African-American rock adaptation of The Wizard of Oz, the Flying Monkeys are a motorcycle gang, whose leader is named Cheetah, after the Tarzan character. Their metal wings are part of their motorcycles, but these apparently dissolved with the witch's other magic, as they are absent when carrying Dorothy and her friends back to the Emerald City.
- In 1976, two statues of winged monkeys were erected on the rooftop of a mattress store called "Emerald City of Oz" in Burlington, Vermont. In 1996, the statues were moved to the roof of Union Station (now Main Street Landing), and statues of baby monkeys were added in the winter of 2004–2005. Two more statues of winged monkeys were installed on the roof of the nearby Waterfront Theatre in the 1990s.
- They subsequently appear in the early 90's cartoon version of The Wizard of Oz, with one of them named Truckle serving as the Wicked Witch of the West's chief sidekick. He's shown as capable of speech and even gets to wear the Ruby Slippers for a brief time.
- 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 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. This speech pattern becomes less pronounced in A Lion Among Men and Out of Oz, the third and fourth volumes in Maguire's "Wicked Years" cycle.
- In The Muppets' Wizard of Oz, the Winged Monkeys are formerly a rather peaceful group of "motorcycle enthusiasts" and are played by Sal Minella, Sweetums, Crazy Harry, Black Dog, Calico, Old Tom, Spotted Dick, and Aretha from Fraggle Rock. The Winged Monkeys were placed under the Wicked Witch of the West's control when she took possession of their Magic Biker Cap. Forced to do her bidding, the Winged Monkeys rode their motorcycles through the skies of Oz, performing the Wicked Witch of the West's dirty work. Once she was defeated upon melting in a bathtub filled with tap water, Dorothy returned the Magic Biker Cap to Sal Minella, thereby restoring the Winged Monkeys' independence.
- The 2007 Sci Fi television miniseries Tin Man depicts a re-imagining of Baum's world of Oz, including bat-winged monkeys called "mobats" that are the familiars of the sorceress Azkadellia which come from tattoos on her chest.
- In Bill Willingham's Vertigo comic book series Fables, a winged monkey named Bufkin is a clerk and librarian in the Business Office belonging to the government of Fabletown, a community of refugee fairy-tale characters ("Fables") living in modern-day New York City. It has yet to be revealed how he became a citizen of Fabletown, but it is known that Oz is one of the mythical "Homelands" conquered by the Adversary that forced many Fables to flee to the "real" world, and was given over to the Nome King to rule in the Adversary's name. Though somewhat scatter-brained, lacking in wisdom, and partial to alcohol when he can find it, Bufkin has a surprising amount of knowledge gleaned from the vast array of reference material in the library. After becoming separated from Fabletown and losing his wings in a conflict with the witch Baba Yaga, Bufkin eventually makes his way back to the lands of the Oz books, and in the wake of the Adversary's defeat by Fabletown, leads an uprising that deposes the Nome King's rule. Bufkin goes on to have other adventures across the Homelands before settling down in his old age and dying of natural causes.
- Winged monkeys or flying monkeys have been mentioned in television series such as The Simpsons, Buffy the Vampire Slayer and Two and a Half Men, and have appeared or been referenced in films such as Hunter, Wayne's World, Jumanji and Inkheart.
- The Winged Monkeys appear in Dorothy and the Witches of Oz.
- Beyond Oz, winged apes called "clakars"[clarification needed] appear in "While the Gods Laugh" by Michael Moorcock, the second published novelette featuring his character Elric of Melniboné; the novelette was later republished in different collections.
- In the 2012 film The Avengers, Nick Fury, portrayed by Samuel L. Jackson calls Hawkeye and Erik Selvig (who had been hypnotized at the start of the film) two of Loki's flying monkeys. At this remark, the Asgardian hero Thor is confused, not knowing what a monkey is (and not having read or seen The Wizard of Oz) whilst Captain America excitedly announces that he understood the reference, having come from a source from before when he was frozen during World War II.
- The Winged Monkeys appear in Oz the Great and Powerful. Oscar Diggs was able to befriend a Winged Monkey named Finley (voiced by Zach Braff) after using an illusion to save him from a lion. The film also included Winged Baboons which make up the armies of Theodora and Evanora. Unlike Finley who can speak and behave like a human, the Baboons are feral and vicious and cannot speak.
- In the music video "Heretics and Killers" by Canadian band, Protest The Hero, the band is seen performing in the monkey suits. A newspaper at the beginning also indicates the monkeys are out of work so they try working and other things to make money.
- The Winged Monkeys appear in the third season of Once Upon a Time. The Wicked Witch of the West sends one out to collect a sample of the Evil Queen's blood for her potion. The Wicked Witch sent a Winged Monkey to make her presence known to the Evil Queen. Before it can attack Robin Hood's son Roland, the Evil Queen turned it into a plush toy and gave it to Roland. Another Winged Monkey assumes the form of a man named Walsh (played by Christopher Gorham) and becomes in a relationship with Emma Swan for eight months. However, when she declines his marriage proposal to go to Storybrooke, he reveals his true form and attacks Emma. Emma fights back and knocks him off a building. Though he vanishes into smoke before he can hit the ground. When Emma is back in Storybrooke, the Winged Monkeys start taking its inhabitants one by one in order to be converted into Winged Monkeys. In "It's Not Easy Being Green," it was revealed that Walsh was the previous Wizard of Oz before being turned into a Flying Monkey by the Wicked Witch of the West. After the Wicked Witch's defeat, everyone who was turned into a flying monkey return to their human forms.
- The Winged Monkeys appeared in the 2013 animated film Legends of Oz: Dorothy's Return (based on Dorothy of Oz).
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