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Season 2 Blair Waldorf and Series 1 Tony Stonem as the manipulative, eternally scheming antagonists we're supposed to hate but end up loving more than the protagonists.
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Seth Cohen as the dorky sidekick who is actually more adorable and lovable than the main character.
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Sandy and Kirsten Cohen as the cool parents every teen wishes was their own.
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Julie Cooper-Nichols as the bitchy parent no teen wishes was their own.
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Season 1, "I killed a man" Serena van der Woodsen and Season 2 and beyond Summer Roberts as the eternally loyal (and gorgeous!) female sidekicks who, in the right moment, can be counted on for a good punchline.
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Chris Miles as the slacker sidekick always making the wrong decisions but never less than hilarious making them.
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Jal Fazer as the badass conscience of the group who can always be trusted to lend an ear and give great advice.
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Mackenzie as the rich snob trying to protect his turf from the invading poor heartthrob.
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