The Joker
Ed Westwick's drunken, disturbed Chuck Bass has drawn comparison's to The Dark Knight and Heath Ledger's final performance. Interestingly, there was an episode of Gossip Girl season called The Dark Night!

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Gossip Girl Season 2 Episode 13 Quotes

Blair: Whatever you're going through, I wanna be there for you.
Chuck: We've talked about this. You are not my girlfriend.
Blair: But I am me. And you are you. We're Chuck and Blair. Blair and Chuck. The worst thing you've ever done, the darkest thought you've ever had, I will stand by you through anything.
Chuck: And why would you do that.
Blair: Because I love you.
Chuck: Well, that's too bad.

Serena: I don't know if I can go away right now. My family is a disaster. My brother is lonely, my mother is losing it, and Chuck has publicly disowned our family.
Aaron: Are you sure it's your family you don't want to leave, or someone else?