Chuck Bass

''' Charles Bartholomew Bass is a character derived from the Gossip Girl series and is played by Lauren. He is portrayed by Ed Westwick. He is a twenty year old human being that prefers to go by the name Chuck Bass. Gossip Girl has nicknamed him CB. Chuck is a bisexual male and is currently single. If you wish to contact this character's owner, please click here. '''

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Chuck is a twenty year old resident "bad boy" of the Upper East Side. Charming and good looking, he grew up in the Upper East Side with his three best friends and fellow elites: Nathaniel "Nate" Archibald, Nate's longtime girlfriend Blair Waldorf, and future-stepsister Serena van der Woodsen. His father is Bart Bass, a self-made billionaire owning Bass Industries, an international real estate and construction company.

Chuck is often described as the bad boy of his circle and is known to be a playboy who sees women as recreational tools. Throughout his early and late teenage years, his friends have witnessed (on many occasions) semi-naked girls or escorts walking out of Chuck's suite. In addition to this, he was often seen skipping class and smoking marijuana, sometimes convincing his best friend Nate to join him. He tells Nate that the three things he cares about in life are "money, the pleasures money brings him, and Nate". In addition, he enjoys manipulating people and causing drama, often teaming up with Blair Waldorf, who shares that similar interest.

Although he is shown to have some serious vices, such as attempting to rape both Serena and Jenny the very night that Serena returned home from a year spent away at a boarding school, a more sensitive side of him is shown later in his teenage years, such as his loyalty to Nate and his hurt at his father's disapproval of his lifestyle. At sixteen, Chuck purchased a burlesque club, Victrola. After Nate and Blair break up after many years spent together, Blair visits Chuck at Victrola where she ends up performing on stage, and she later loses her virginity to him in the back of his limo. Though she tries to pretend it never happened, he wins her over on her birthday when Nate fails to show up, and Chuck reveals he bought her the necklace she had wanted for her birthday. He also admits that he feels butterflies for her, which is a turning point in the notorious playboy's life. This revelation leads to a clandestine sexual relationship. Although Chuck falls hard for Blair, she eventually leaves him to return to Nate, who has realized he wants her back.

As Bart Bass and Serena's mother Lily Van der Woodsen's relationship progresses, they decide to move their families in together, and Lily, Serena, and Eric (Serena's younger brother) become a second family to Chuck. Eric, in particular, becomes an important brother figure, choosing Chuck as the first to learn of Eric's homosexuality.

When Serena begins receiving mysterious packages (porn in the mail, alcohol delivered to her at school, etc...), she automatically blames Chuck and Bart kicks him out. When Serena discovers that the culprit was actually Georgina Sparks, a manipulative, drug addicted socialite, she apologizes, and Chuck and Serena are horrified to discover that Georgina is back in town. It is around this time that his friends learn that Chuck lost his virginity to Georgina in the sixth grade. Chuck and Blair team up to take down Georgina, and the process brings them closer again.

At his father and Lily's wedding, Chuck apologizes and confesses to Nate that he was in love with Blair. His honesty allows the two of them to rebuild their friendship. During the reception, he locks eyes with Blair and gives a very personal speech about forgiveness and persistence. She takes that as an apology and the two kiss. However, as they are about to embark on a trip to Tuscany, Chuck gets cold feet and ends up standing her up at the helipad. He is last seen using his trademark "I'm Chuck Bass" line on Lily's interior designer, Amelia, and reverting back to his old whoring ways, as Blair leaves for Tuscany without him.

Blair chose to leave for Europe and stay in Europe alone. Chuck regretted his actions but told this to Blair too late as she was already dating Lord Marcus Beaton. Blair asks Chuck to tell her he loves her, but his fear of commitment stops him.

In order to gather material for a story, Dan Humphrey (Serena's on-again, off-again boyfriend) tags along with Chuck for a night, ending with the two of them in jail after a drug-induced fistfight. While in jail, Chuck tells Dan in confidence that Chuck's mother died while giving birth to him, and that his father blames him for her death, which explains their icy relationship. When Chuck later discovers that Dan was using him for a story, he feels betrayed and tells Dan that he was lying about all of it.

Soon after, Chuck's father is killed in a car accident. Lily legally adopts him so that he's able to own Bass Industries, making Serena and Eric his sister and brother. When Blair begins dating Nate again, Chuck realizes his true feelings for her, and Blair realizes that she still has feelings for Chuck as well. She breaks up with Nate after Chuck admits to Blair his true feelings and the two finally begin a relationship.

Lily decides to start moving on and ends up marrying her first true love Rufus Humphrey, Dan (Serena's on-again, off-again boyfriend) and Eric's best friend Jenny's father, adopting both Dan and Jenny into the family and officially uniting the Van der Woodsen's, the Humphrey's and the Bass'.

Soon after Lily and Rufus marry, however, Lily's first husband (the biological father of both Serena and Eric) Doctor William Van der Woodsen returns to the Upper East Side where he begins scheming to win Lily and his children back. Schemes include framing Rufus with adultery and trying to turn his children (Serena and Eric) against Rufus, though the more devastating scheme William set in motion was purposely misdiagnosing Lily with cancer in hopes that she would rely on him to treat her. He would use that time to win her back.

Chuck, devastated by the false news of Lily's illness stays by her side throughout the course of those few months that she believes she is ill. William slips medications into her daily diet to show symptoms of the cancer she is supposed to be victimized by, but Chuck (along with Jenny) learn that William was playing games to win his family back, and eventually William up and leaves his family once again.

Throughout the course of the year, Chuck struggles to run Bass Industries to his deceased father's impeccably high standards. He opens up a hotel, The Empire where he resides in a penthouse, around the same time a woman claiming to be Chuck's biological mother shows up. Stating that his father had lied about her existence and that she had been longing for a relationship with her son for many, many years.

Soon after believing that this woman was, in fact, his biological mother, Chuck, due to a sexual harassment suit at work, temporarily signs over The Empire to his biological uncle. The woman claiming to have been his biological mother betrays him and signs the hotel over to his sinister uncle, Jack Bass, who has previously attacked Lily and slept with Blair.

Chuck and Blair agree to team up to take down Jack, but Chuck ends up offering Blair to Jack in exchange for his hotel. When Jack tells Blair this, she breaks up with Chuck at Dorota (Blair's housekeeper) and Vanya's wedding. 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 late. Chuck, thinking she is finally over him, leaves the building heartbroken and nearly suicidal. When he gets home, he sees that Jenny Humphrey (Dan's younger sister) has arrived looking for Nate. The two drunkenly sleep together, heartbroken that their true loves don't return their feelings.

Blair appears later in Chuck's suite, apologizing for being late, and the two reunite. Chuck is about to propose to Blair at the hospital, as they visit Dorota and her new baby, when Dan appears and rashly delivers a punch to Chuck's face. He then forces Chuck to tell Blair what happened between him and Jenny. Blair breaks things off with Chuck and informs him it's for good. She also threatens to ruin Jenny's life if she doesn't leave Manhattan immediately for good.

Chuck then travels to Prague to escape New York for a while, feeling as though he has nothing left. He gets robbed by three muggers who insist on taking the ring that Chuck intended on proposing to Blair with and when Chuck puts up a fight, he gets shot in the stomach.

Chuck is alive and well after the attack, having been rescued by Czech girl, Eva, who has no idea of his wealth or of who he is. He creates a fake name and persona as he no longer wants to be the manipulating Chuck Bass. He eventually reveals who he really is and returns to New York with her, at the request of Blair and Serena.

Everyone is able to see how changed Chuck is; no longer phased by the gossip, rumors or scandals of the Upper East Side, even going as far as to give Eva five million dollars to donate to a charity of her choice, while, in the meantime, Blair insists she no longer loves him, but still schemes to undermine his new relationship.

Blair teams up with Serena and Dan, using their knowledge and kills to track down pieces of Eva's past that she could use against Eva; Dan eventually finding out that Eva used to be a prostitute. While Chuck was unaware of this piece of information prior to Blair informing him, he and Eva look past it and continue their loving and budding romance.

Unaware of the schemes Blair is tossing at Chuck and Eva, Lily asks her to deliver Chuck's passport that the police had recovered from the muggers in Prague. Instead of leaving his passport in his suite as directed, Blair, instead, plants his passport in Eva's suitcase, making Chuck believe that Eva had, in fact, known Chuck was the billionaire everyone knew him to be.

Chuck falls for Blair's scheme and breaks up with Eva. He realizes his mistake when Lily asks if Blair had returned his passport 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 states that he was foolish to believe that an angel like Eva could ever love somebody like him, and declares war on Blair.

Chuck works to sabotage various aspects of her life ranging from making her lose internships, to inviting Jenny Humphrey back to town. Their war on each other soon blossoms into an enemies-with-benefits relationship, and Chuck accidentally tells Blair that he loves her during sex though not knowing whether his words are true, Blair chooses to gloss over the moment.

Although Chuck and Blair spend time striving for different ends which will eventually alienate each other (Blair to become the face of Nate's mother Anne Archibald's charity, Girls Inc, and Chuck to increase the revenue of The Empire by returning to his bad boy persona), Blair makes the decision to attend Chuck's 'Saints and Sinners' party in order to confront him. Chuck confesses that he loves her, and the pair kiss in front of everyone after the curtain concealing them is pulled down. Anne tells Blair that she can no longer be a part of Girls Inc just as Chuck's publicist KC tells Chuck that she thinks Blair will be good for business. Blair re-thinks her decision to sacrifice it all for their relationship, and she and Chuck break up once again. Chuck promises he'll wait for her, and both affirm their belief that their love will reunite them in the end.

On thanksgiving Chuck and Blair run into each other at Serena's house, Chuck offers to leave but She tells him that she was heading to the JFK airport anyway and came to drop off the traditional pie and that they should get used to this. They hear about Serena being hospitalized and while they're sharing that maybe nothing can change between them, Jenny walks in and their conversation interrupts. While driving Blair home, Chuck tells her that he showed up only for Serena. After that Blair still sends him her traditional pie, saying that even if they can't be friends it doesn't mean that they aren't.

It was later revealed that Lily was going to sell Bass Industries instead of adopting Chuck the company back. He sets off to New Zealand, which is not too far from Australia, where his uncle Jack Bass is currently living, and Chuck returns to the Upper East Side with revenge for Lily. Chuck's new love interest Raina and her father, Russell Thorpe, a former rival of Chuck's late father Bart Bass.

During this time, however, Chuck learns that Russell wished to acquire Bass Industries for himself by blackmailing Lily into getting Chuck to sign over his father's company. It is revealed that Lily paid off law officials to falsely accuse and imprison a young English teacher named Ben Donovan for statutory rape, hoping that imprisonment would keep the English teacher away from her daughter Serena that had fallen in love with him during her early high school years.

After being released from prison, Ben and Serena start seeing each other once again, and Ben's mother manages to steal the affidavit that Serena had been safekeeping for her mother, stating that Lily had, in fact, bribed police officers, judges and so forth to imprison Ben. Ben's mother handed the affidavit over to Russell, who was ready to blackmail Lily into signing over her adopted son's company to him. Lily, however, made a phone call to the DA's office and arranged to make an official statement about her wrongdoings.

Lily escapes jail time, though works to restore Ben's life as well as she could manage. First having his criminal record cleared and the paying a settlement to help him start a new life for himself, despite his broken relationship with her daughter. It's during this time that a private investigator that Chuck's father had hired to trace Lily, Serena and Eric's pasts turns up with information that he hands over to Chuck, showing that Lily and Rufus, while in their early twenties, had created a child together. Lily had never told Rufus about the child, for they had broken up when Lily had found out, and she had put the child up for adoption.

The private investigator had learned that Lily's son (Andrew) was living in Italy, and Chuck takes it upon himself to encourage Lily to uproot the family that had been residing in Manhattan and move them to Italy so they could begin the search for their missing family member. There, Chuck and Lily open two student housing buildings in an attempt to start building their lives (and fortunes) in Livorno, Italy.