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Chuck is often described as the "bad boy of his circle." Chuck is a playboy and womanizer who sees women as recreational tools. In the pilot episode, Chuck attempts to rape both Serena and Jenny Humphrey.

In the TV series, step-brother to Serena and Eric van der Woodsen.

Chuck Bass is introduced by author Cecily von Ziegesar in her Gossip Girl series of teen novels, the first of which was published in 2002.

Chuck is the resident "bad boy" of the Upper East Side, and like Blair, is both vengeful and manipulative; the two often scheme elaborate plans together.

As the show progresses, Chuck develops a softer side, specifically towards Lily, Eric, and Serena, his adoptive mother, brother, and sister.

In the twelfth book in the series, Gossip Girl: It Had To Be You (2007), Chuck is rejected from colleges because of poor grades and is sent to military school by his father.

When next mentioned in Gossip Girl spin-off, The Carlyles (2008), it is stated that Chuck never showed up to military school, and his whereabouts thereafter are unknown.

She’d previously spoken about the “unique” relationship she shares with Di Caprio in an interview to Glamour.

“We know each other in a very unique way, I think, because of the experience we both had on that film and having to take care of one another,” she explained.

Lazy, and vain, Chuck's only interests are sex and money, and he is frequently chided by his father for lacking ambition and performing poorly in school.

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