Pennywise
Pennywise is one of the creepiest monsters that Stephen King has ever invented, starring as the antagonist of 1986 horror novel It. The shapeshifting clown has recently returned to the spotlight after the popularity of the 2017 movie adaptation of King's novel.
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Catwoman
Selina Kyle, aka Catwoman, has been enemy, friend, lover, and fiance to Batman. She'll play a key role in the upcoming animated movie Batman: Hush, which is based on the critically acclaimed comic of the same name.
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Anastasia
Anastasia was a very real Grand Duchess of Russia, and her story was fictionalized into a popular animated 1997 film.
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Green Ranger
Tommy Oliver was originally an enemy to the Mighty Morphin Power Rangers as Rita Repulsa's Green Ranger. However, after being freed from her spell, Tommy went on to become the greatest Power Ranger of all time.
Judge Dredd
Judge Dredd lives in a future where Judges get to also be jury and executioner.
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Ariel
Ariel was a princess of the sea who dreamed of a life on land. She eventually became a bridge for her kingdom and the humans, one that was expanded upon by her daughter, Melody.
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San
San is the female lead in the anime movie Princess Mononoke. Protagonist Ashitaka first encounters her while she's riding a wolf. Raised by the pack, San has grown to resent humans despite being one herself.
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Spider-Man, Dr. Octopus, And Spider-Woman
In Spider-Man: Into the Spider-Verse, Miles Morales befriends Peter B. Parker and Gwen Stacey, a Spider-Man and Spider-Woman from different universes. He also runs into his universe's version of Dr. Octopus, Olivia Octavius.
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Captain American, Red Skull, And Black Widow
These three have been in plenty of comics, TV series, and movies, but the three pictured above seem to be from the MCU specifically--seeing as Red Skull isn't offering any refunds for the Soul Stone test.
Night King And Dragon
Both of these characters hail from Game of Thrones, and neither one is easy to talk about without spoiling the show so we'll refrain.
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Samwise And Galadriel
Both allies of The Lord of the Rings' Frodo, Samwise is one of the Hobbits that compose the Fellowship of the Ring and Galadriel is a royal elf.
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Captain America
Steve "Captain America" Rogers was a normal New Yorker who became one of the World War II's greatest heroes through a super-soldier serum.
Wonder Woman, Supergirl, And Superman
Wonder Woman and Superman are both a part of DC's big three alongside Batman, while Supergirl is Superman's cousin. The Wonder Woman and Superman pictured here are both a part of the DC Cinematic Universe, while Supergirl's costume suggests she's The CW's Arrowverse version of the character.
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Tinker Bell, Peter Pan, And Captain Hook
All three of these characters are from Peter Pan, although Peter and Tinker Bell are protagonists while Hook is an antagonist.
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Iron Man
Tony Stark managed to build the first Iron Man armor, the Mark 1, in a cave. With a box of scraps.
Skeleton King
The Skeleton King is the boss encountered at the end of Diablo III's The Royal Crypts--which is located in Act I of the game.
Captain America, Iron Man, And Thor
Steve Rogers picked up Mjolnir, Tony Stark donned the Iron Man Mark LXXXV armor, and Thor wielded Stormbreaker in the fight against Thanos in Avengers Endgame. And it was glorious.
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