Chuck Bass had highs and lows through six seasons of Gossip Girl. What started as a villainous arc with Blair turned into the best character development on the show.
Chuck turned from a self-absorbed, rich bully to a worthy partner and love interest. Despite his eventual happy ending with Blair, he suffered loss and betrayal to get to where he was supposed to be.
10 His Rivalry With Jack
Whenever Chuck reaches out for a family, it never seems to work in his favor. After Bart’s death, Chuck’s uncle resurfaced and dragged him back from a bender in Bangkok. Jack was friendly until he learned that Bart was leaving the entire company to Chuck. It wasn't the first time Jack betrayed Chuck.
After Chuck and Lily run Jack out of town, he resurfaces again. His motive is the same, to steal Bass Industries from Chuck. For a long time, Jack never viewed him as family, only an obstacle.
9 Most Of His Girlfriends Leave Him
Chuck always had a complicated past with women. His aggression was a fact that he acknowledged and tried to make amends for. But when he tried to move on, virtually all the women he formed attachments to decide to leave him.
When he tried to shed the Bass name and move on with Eva, she wasn’t able to cope with his lifestyle after she spent more time with him. With all the good intentions he had, it never seemed to be good enough.
8 He Loses His Family Over Jenny
Even after Bart died, Lily was adamant that Chuck still be in her family. She formally adopted him as a business decision but also because she loved him. When she married Rufus, the situation got more complicated. Chuck made many mistakes and sleeping with Jenny Humphrey was one of them.
Jenny wanted her first time to be special but because she was vulnerable, she decided to sleep with Chuck. The Humphreys were furious that Chuck took advantage of Jenny and effectively kicked him out of the only family he ever had.
7 Dan Uses Him For A Story
The first time Chuck mentions his mother in a serious context is when he and Dan get arrested for brawling in public. Dan is the first one on the show Chuck opened up to about his mother and told Dan the reason why his father hated him.
Dan and Chuck never got along and their dynamic became even more fraught after Chuck realized Dan was getting close to him just to write a story. Chuck’s vulnerability was thrown back in his face and no matter what, Dan was the villain of that particular story.
6 He Never Found Out What Happened To His Mother
The storylines featuring Chuck’s alleged mothers would give you whiplash. From a young age, Chuck was told that his mother died in childbirth. Chuck then told Dan that his mother died in a plane crash in the Andes when he was six. Neither of these seemed to be true with Elizabeth Fisher showed up.
Elizabeth claimed to be his mother and that Bart had lied about her death. What she came to town for was not to form a relationship with her son but help his uncle steal his company. They told Chuck later that Elizabeth was not his mother. Chuck never finds out the truth of it and once again holds the trauma of his family abandoning him.
5 His Relationship With Lily
After Lily began dating Bart, Chuck found a family with the van der Woodsens. He was ecstatic when his father proposed. He would be getting a real family which he took seriously. Lily became his surrogate mother but it was ruined after his father died.
Chuck learns that the reason his father was in the car when he died was because he was confronting Lily about her decision to leave him. Even after Chuck and Lily make amends, she continues to disappoint him after deciding to sell his father’s company without telling him.
4 He Made Blair Think He Hadn’t Changed
For most of season five, Blair works to obtain the perfect wedding. Chuck attempts to stick true to his decision to let her go. But Blair constantly looks for reasons for Chuck to remain in her life. One of her main obsessions is thinking that Chuck was trying to trick her and that he hadn’t changed.
Chuck knows the only way for Blair to move on is to push her away. He kisses her at Sleep No More so she will go back to Louis, thinking that he is still the vile human being he used to be.
3 He Would Have Died For Blair’s Ring
Blair learning that Chuck had slept with Jenny was devastating. But what was even worse was the fact that very night he was planning on proposing to her on the top of the Empire State Building. Chuck keeps the ring after Blair breaks up with him and he spends time in Prague.
While in the red-light district, Chuck is mugged. And even though Blair left him again, he refuses to let go of the ring the muggers are after. They shoot him and he passes out on the street, still refusing to let go.
2 His Father Could Never Love Him
Bart had many excuses for not showing his son the affection that every child needs. Of course, Chuck made mistakes, but Bart’s love was never unconditional. It seemed that Bart disliked his son for his partying ways and poor decision making. But no matter how hard Chuck tried, it never seemed to be enough for Bart.
Bart seemed to turn a corner when he realized Chuck thought Bart blamed him for his mother’s death. But that was just another excuse. What Bart disliked was that Chuck had the potential to be a better person than him. He continues to lie to Chuck until his death.
1 He Had To Let Blair Go
One of Chuck’s constant struggles in life was becoming the type of person that could function in a healthy relationship. Blair had always been his ultimate goal and he always lost her. But the most tragic breakup was when Chuck realized that to be a good person, he had to let Blair go.
After a near-death experience, Blair and Chuck get back together briefly even though she was engaged to Louis. Blair described this as something they couldn’t fight even if they wanted to. Chuck realized that Blair had to choose to be happy instead of being with him. Even though Blair initially fought him on the decision, he knew they had to move on.
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December 12, 2020 at 11:00AM
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