Charles Bartholomew Bass is a fictional character in the novel and television series Gossip Girl. In the TV series, he is portrayed by British actor Ed Westwick. Although he is a secondary antagonist in the original book series, the TV series elevates him to an antiheroic main character, and the male lead of the show, where he is noted for his financial ambition, hedonism and personal style.
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. In the TV series, he is also step-brother to Serena and Eric van der Woodsen.
Novel 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. In the novels, Chuck is a relatively minor character, and has a series of flings with male and female characters across the course of the series. He got his nickname, Chuck Bass, from his signature chuckle in a bass tone, which often sounds like a raspy whisper. Chuck's role is initially that of an antagonist to the main characters. Chuck resides with his family at the Plaza Hotel on the Upper East Side and attends school at the Riverside Preparatory School for Boys on the Upper East Side, along with scholarship student Dan Humphrey. Chuck is largely lonely as his only friends are Blair, Nate and Serena, but is tolerated by the others because of his family's enormous wealth. He is described as having flamboyant fashion sense, with a penchant for scarves, and has a pet monkey named Sweetie. 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.
TV series
Constance Billiard School is an exaggerated version of Gossip Girl author Cecily von Ziegesar's alma mater, the Nightingale-Bamford School. 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.
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.
Season 1
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. His father is Bart Bass, a self-made billionaire, which is irregular, compared to the Bass' old money friends. Although he is popular in school, he doesn't have many other friends than the three mentioned, and it's learned that others hang out with him due to his father wealth. Chuck is often described as the "bad boy of his circle", being a playboy and womanizer who sees women as recreational tools. He frequently skips class and smokes cannabis.
When speaking about Serena in the pilot episode, Chuck says, "Serena looked effin' hot last night. There's something wrong with that level of perfection. It needs to be violated." In the same episode, Chuck attempts to rape both Serena and Jenny Humphrey. With time, he attenuates his behaviors as a sexual predator and becomes more of a manipulating womanizer. However, his lecherous attitude continues as he makes multiple advances on his step-sister at the time, Serena.