Mischievous, sly and malicious antagonists. They trick others and often cause troubles for their own amusement.
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- Shadow Animals
- Shadow Darma
- Shadow Odlulu
- Shadow People (Where's Waldo?)
- Shadow Waldo
- Shadow Wenda
- Shadows (Where's Waldo?)
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- Shinnok (Mortal Kombat Legends)
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- Sledgehammer O'Possum
- Snotty Boy
- Sol (Gacha League)
- Spud
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- Sugar Dimples
- Sylvester J. Pussycat, Sr.
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- Tanya
- Terry Duckworth
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- The Collector (The Owl House)
- The Dazzlings
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- The Nogitsune
- The Rowdyruff Boys
- The Waiters (Iron Virgin Jun)
- The Walrus (Pingu)
- Timmy and Tommy Tibble
- Tom Cat
- Tom Sawyer (The Fairly Oddparents)
- Triple H
- Trix
- Tybi
- Tyler Nguyen-Baker