Chuck BassPlayed by: Ed Westwick
I'm Chuck Bass. That's his trademark line - but who is he, really? We learn a little bit more every week about this, rich and pompous character who desires the finer things in life ... such as expensive clothes, alcohol and sex.
He's as obnoxious - but hilarious - as he is wealthy and charming at times. Everyone may despise Chuck Bass, but there's no question that he is the most connected kid on Upper East Side. He is the son of Bart Bass, a business magnate.
Chuck has come close to a sexual encounter with Jenny Humphrey and makes dirty remarks at new stepister Serena van der Woodsen (her mom Lily married Bart at the end of Season One), but his true sexual fascination is Blair Waldorf.
She lost her virginity to him in the back of his limo in Season One, and ever since, he's pined for her like no girl he has ever known. In Season Two, they have been playing a cat and mouse game, cashing each other, unsure of their true feelings.