The essay charts Chuck’s beginnings as a ceasar-mopped brat on a city bus to an emotionally mature man willing to raise a child who isn’t his own. Whether you agree with the analysis or not, poring over Chuck’s character development — charted from the pilot right up to the Season 5 Finale — is what obsessively loving Gossip Girl is all about.
Chuck Bass in the pilot episode is one BAD dude–someone we may have crossed the street to avoid, even. However, we want to address a disconnect between pilot!Chuck to rest of the show/last 110 episodes!Chuck. Yeah, Chuck in the pilot is as villainous as a villain could be. However, it’s also important to remember that his MOTHER is also “addicted” to Paxil and he is a frequent passenger on a NYC Metro bus. These might seem like minor details, but they’re important.
After sleeping with Blair for the first time, Chuck experiences two things that up until that moment were completely foreign to him: he feels “something in [his] stomach fluttering.” Chuck actively pursues only Blair, when before, it repulsed him to sleep with the same woman twice. When Blair sleeps with Nate (and gets back together with him), Chuck is crushed. At Bart and Lily’s wedding, he gives a beautiful speech about the power of perseverance when it comes to love and then tells Blair, “I know I said some horrible things, even for me.” This is so significant because it is the first time Chuck Bass has even come close to an apology. In this same episode, he admits to Nate that he is in love with Blair, the first time he’s ever admitted to having deep romantic feelings for anyone.
On Chuck’s Ongoing Maturation:
Giovanni Rufino/The CW 2011 The CW Network
The very best thing about Chuck’s evolution is that even though he has become a more emotionally healthy and mature man, able to separate love from legacy, he is still fundamentally Chuck Bass. He still battles with his inner bad boy and becoming the man he wants to be – what people expect from him versus what he desires from himself. He still has his vices, he just no longer allows them to be destructive. He still loves his purple ascots and bowties, he still walks with that Bassian swagger, he still uses his name and money to get ahead, he can still freeze people to their spot with his snark and one-liners–he just uses these things for good now.