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.
When speaking about Serena in the pilot episode, Chuck says, "Serena looked effin' hot last night.
In episode seven, "Victor/Victrola", Chuck purchases a burlesque club, Victrola.
After Nate and Blair break up, Blair visits Chuck at Victrola where she ends up performing on stage.
Chuck is largely friendless, but is tolerated by the others because of his family's enormous wealth.
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 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.
Constance Billiard School is an exaggerated version of Gossip Girl author Cecily von Ziegesar's alma mater, the Nightingale-Bamford School.
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 name, Chuck Bass, from his signature chuckle in a bass tone, which often sounds like a raspy whisper.