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Ollie is a wingless monkey from the Dorothy must die series. Ollie is Maude's brother and a part of The winged and wingless ones ruled by Queen Lulu. He was rescued by Amy Gumm and a goth munchkin named Indigo when he was strapped to a long pole for the crime of sass. Amy was shocked to hear him talk, which made him feel offended and he explained that of course he can talk. Ollie attempted rescuing Maude from the Scarecrow's lab on his own and ended up getting help from Amy disguised as Astrid. He was friend and an ally of Amy and The Order.

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