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Walking with a swagger in his multicolored arsenal of trench coats and pastel suits are an awesome sight. No color is too bold, no pattern is too tacky, and no outfit is too Hamptons-chic for Chuck Bass. With his collar always turned up while speaking in a tone just above a whisper and acting like it's painful to engage in a conversation, he never lets people forget who he is, as he always has a hidden agenda. Frequently using the line "Because I am Chuck Bass" as a justification for a particular behavior keeps people interested as well as confused. His pointless and detrimental damage to his friends' social life, for no reason other than because he can, have created his bad reputation. For years he has tried desperately to win the approval of his soulless and emotionally inept father, but Chuck has neglected the obvious fact that he is turning into his dad. And, instead of telling the woman of his dreams that he loves her, he mentally tortures her. With his tagline "I'm Chuck Bass" and downplaying his multitude of deposits into his offshore accounts, most people would steer clear. Although women love a man who has a sophisticated style, he can't have the woman he really wants because Chuck Bass fails at his attempt to change.
Charles Bartholomew "Chuck" Bass was born and raised in Manhattan's most elite social circles. He appears to be the ultimate playboy; interested only in women and money. However, at times, he is seen to show some heart and compassion. He doesn't have any true friends, but is accepted by most of his peers because of his fathers' status. Families, friendship, and trust are all filtered through the searing stare of Chuck. But, business, revenge, and true love are top on his priority list. Gossip Girl, a television drama, follows the lives of a group of privileged teenagers living in New York City. These teens attend elite high schools, are part of a very influential, high-class society in Manhattan's Upper East Side, each with the goal of attending Ivy League colleges just as their parents did before them. The parents in Gossip Girl come from old, inherited money, and the families are similar to dynasties, where a name is everything and new comers are not welcome.
So, who is the real Chuck? He is the scheming guy people love to hate, who can be found sipping bourbon in a smoking jacket in the middle of the afternoon. But, he's also the insecure, attention-seeking son whose goal in life is to be anything other than a disappointment to his father. Additionally, he's the unscrupulous charmer who flaunts his wealth only because his ego won't let him utter those three important words to his real and genuine love, Blair. Chuck Bass is all of these things, and that's what makes him so great.
He's definitely got the "bad boy" flair. As Blair's immoral counterpart, he's the guy with whom she can live out cruel plots. He never flinches at a challenge, much less a bet, and it seems he's willing to do whatever it takes as long as the benefits outweigh the risks. One night the bet was to "seduce and destroy" a peer by taking on her latest cause in exchange for a night with Blair. It seemed like a challenging situation since this girl was known to be smart enough to know better than to trust Chuck. However, he somehow convinces her that her latest endeavor would benefit with Chuck's financial backing. Unfortunately, the people whom Chuck cares for the most have yet to see his capabilities. His father hates the idea of funding his son's latest endeavor and his disapproval is damaging to Chuck's credibility. Nothing he does will ever win his father's respect and love. After that setback, one would think Chuck would let off some steam by accepting Blair's offer. Instead, he acts unpredictable and maintains his self-respect after she refuses to say the three words she once demanded from him; I love you. The fact that he wouldn't settle makes his personality even more admirable.
Blair Waldorf, the main female character in Gossip Girl, is a socialite who comes from an extremely wealthy family. Her mother, a divorced woman with a prominent career as a fashion designer, never pays much attention to her daughter, which has made Blair rebel several times. Blair once tried to sabotage her mother's fashion show for her own personal benefit. But, when Blair is not suffering through her own identity crisis, she's trying to stand by Chuck as he struggles to redefine himself outside of his father's image. It's never quite clear what Chuck believes, or how much of what he says can be believed, but his love for Blair seems surprisingly consistent. Conversely, Blair's unpredictability is what keeps Chuck interested. He's been known to describe her as not "wasting a breath hurling insults if she didn't think they'd land." And instead of taking responsibility for his own behaviors, Chuck is so enamored with Blair, but tries to downplay it with lines like "Foolish and wretched is the man who builds his happiness on the frail and unstable affection of a woman". No woman can compare to Blair in Chuck's eyes. In fact, it can be said that Chuck disregards all women.
For instance, Chuck is given a chance to change when his dad passes away leaving Chuck's step-mother in control of all the assets. Instead of taking advantage of a new chapter in his life and taking on the challenge of his step-mother, Lily, Chuck continues with his familiar ways of dealing and relating to women. Chuck's closed mind and set ways continue to demonstrate his hatred of women when he mocks Lily's new role. Demeaning women is what Chuck knows best and his reaction to Lily's inherited duties are no different. As his step-mother attempts to dive into the Bass finances, Chuck's only capable of mocking and describing her as "A fine lady is a squirrel-headed thing, with small airs and small notions, about as applicable to the business life as a pair of tweezers to the clearing of a forest".
In addition, Chuck often reflects a feeling that he couldn't care less. His clothes give off an old, worldly English demeanor. And, because Chuck Bass is the richest kid in New York, a bourbon-drinking, womanizing scoundrel that doesn't really give a crap about anyone, he can pull off whatever he wants. He can saunter around in a pink suit and ascot looking fabulous and not care. Whatever anyone thinks doesn't matter to him. He's richer than them, he's more handsome than them, but the one thing he wants and doesn't have, is Blair. Everyone is in love with Gossip Girl's resident billionaire-bad-boy Chuck Bass. Those bow ties and pocket squares, that sneer, those condescending, degrading quips, all have created a mythological anti-hero and to hate him would be a crime, because after all, he is "Chuck Bass".