Charles Bartholomew Bass (Ed Westwick), better known as "Chuck" is the brooding and manipulative anti-hero on "Gossip Girl." Since childhood, Chuck has been friends with other high society offspring, Serena van der Woodsen (Blake Lively), Nate Archibald (Chace Crawford) and Blair Waldorf (Leighton Meester). Known for his ambition and style, Chuck is the son of apathetic business mogul Bart Bass (Robert John Burke). When Bart marries Serena's mother, Lily van der Woodsen (Kelly Rutherford), Serena and Chuck become step siblings. Chuck's father dies in late in Season 2 and he is left with his step-siblings and adopted mother Lily as his only close family.
During the first season Chuck is sly and unlikable, an antagonist to the other characters. His only interests are sex, money and manipulating. Towards the end of the season, as Chuck's on/off love affair with Blair begins to unfold, he becomes a much more compelling character. By Season 3, Chuck shows a nicer side, with some truly loving gestures towards Blair and he maintains a warm relationship with Lily.
While Chuck is still grieving the loss of his father and trying to continue the Bass legacy, a woman appears, claiming to be his mother. An agent of Chuck's evil uncle, Jack Bass (Desmond Harrington), she convinces Chuck to sign over his hotel. Jack runs the business into financial ruin.
The Brontë-esque relationship between Chuck and Blair is the most compelling storyline on the show. Both Chuck and Blair share a vengeful nature, luxurious lifestyles and a love of scheming. This makes for a tumultuous but passionate relationship. Initially their love is hampered by Chuck's inability to commit, but by Season 3 they appear to be in a steady relationship. They are brought even closer when Chuck's long lost mother reappears. However, this relationship is destroyed when Chuck sells Blair to Jack, in return for the hotel. Later, when Chuck is about to propose to Blair, it is revealed that he slept with Blair's enemy, Jenny Humphrey (Taylor Momsen). Blair breaks up with Chuck for good.
Chuck escapes to the Czech Republic where he is shot trying to stop muggers from taking the engagement ring he bought for Blair. He re-creates himself as a humbler man and attempts to start a new life in Europe. Returning to New York with a new beau, he begins a new enmity with Blair when she scares the girl away. A purely sexual relationship between Chuck and Blair ensues, until Chuck accidentally says "I love you." Eventually Chuck and Blair call it quits again and Chuck moves on to sleeping with the daughter of a former business rival.
Chuck Bass' popularity has gained him a place on the annual Forbes Fictional 15 Rich List, alongside Jay Gatsby (The Great Gatsby) and C. Montgomery Burns (The Simpsons). The character has sparked thousands of fan sites, including iamchuckbass.com and an e-how to help enthusiasts become Chuck Bass.
"Why should I be…an usher? I'm Chuck Bass."
"What we're entitled to is a house in the Hamptons; Maybe a perscription drug problem."
"Unless you want dear Nathaniel to know how you lost your virginity to me in the back of a moving vehicle I encourage patience and restraint."