Charles Bartholomew Joseph Bass is a fictional character in the novel and television series Gossip Girl.

[1] Since they were children, Chuck has been best friends with Nate Archibald, Serena van der Woodsen and Blair Waldorf, who is his main romantic interest throughout the series.

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.

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.

Following flings with numerous females and males, his only serious relationship comes near the end of the series, when he begins dating Blair Waldorf, a self-obsessed, luxury loving teenager.

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.

In the thirteenth Gossip Girl novel, I Will Always Love You (2009), it is revealed that Chuck went off to school in California and returned a changed man, and to have dated main character Blair Waldorf in Oxford, England for a year.

It was revealed in preparation for the 2007 TV series debut, Josh Schwartz hired recent graduates of Ziegesar's alma mater to retool several characters.

[2] Chuck Bass was then reconfigured as a more central character, an antiheroic playboy whose on-off relationship with Blair Waldorf serves as one of the show's major ongoing storylines.

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 Blair, his chief love interest, and Lily, Eric, and Serena, his adoptive mother, brother, and sister.

Chuck grew up on the Upper East Side with his three best friends and fellow elites Nate Archibald, Blair Waldorf, and future-stepsister Serena van der Woodsen.

In episode three, "Poison Ivy", Chuck gets interviewed for an usher position for a school event with representatives from Ivy League colleges, and answers the question why he should get the spot simply with "I'm Chuck Bass", a phrase that he continues to utter on multiple occasions throughout the series to justify his behavior or boast about his reputation.

Though she tries to deny the encounter, Chuck buys a necklace for her and admits that he feels "butterflies" in her presence, leading to a clandestine sexual relationship.

When Serena begins receiving mysterious packages (pornography in the mail, alcohol delivered to her at school), she automatically blames Chuck, who had made multiple remarks expressing his desire to sleep with her.

A week later however, as they are about to embark on a trip to Tuscany together, Chuck gets cold feet when his father praises how the relationship with Blair would make him "grow up".

Chuck tries desperately to win Blair back, doing everything from banning all of the other Upper East Side men from dating her to asking her to meet him on top of the Empire State Building.

Blair decides that Chuck is her true love and she's going to meet him, but Dorota suddenly goes into labor and she ends up being two hours late.

In the first episode of season four, we find that Chuck is alive and well, having been rescued by Czech girl, Eva (Clémence Poésy) who has no idea of his wealth or who he is.

He realizes his mistake and begs her to take him back, but she refuses, saying that he showed his true feelings by continuing to believe Blair over anyone else.

Chuck, however, manages to save the company after it is revealed that Russell accidentally killed his wife in a building fire that Bart was originally accused of.

He gets drunk and embarrasses Blair in front of Louis' mother, and later tries to force himself on her, while pushing her down and smashing a glass window right next to her face, after she tells him about her engagement.

However, his heartbreak soon becomes apparent when he receives an invitation to Blair's upcoming wedding, which causes him to drive recklessly and get into a motorbike accident.

However, it is only when Blair reveals to him that she is pregnant with Louis's baby does Chuck begin feel again – he is shown crying over the revelation at the end of the episode.

He resolves to keep his distance from her after that, but in "The Big Sleep No More", a conflicted Blair seduces him in the hope to prove that his efforts to be a better man is just a ploy to win her back.

For the next few episodes he chases her to discover what has changed her mind – unbeknownst to him, Blair has made a pact with God over his life, where if she breaks her promise to Louis, Chuck will surely die.

In "Cross Rhodes", Blair realizes she now has feelings for Dan, and Chuck and Serena struggle with watching their loves with their friends.

He's the charming devil at the center of all the intrigues, the go-to guy when something naughty needs to be said and he's the most self-aware of the Upper East Side high schoolers.

And his chemistry with Leighton [Meester] — when we saw them together on screen and the power of the two of them working together but also being attracted to each other, which really inspired us to grow that character and give him some more layers.