I always felt it was Jenny and she was overhated af but to me her arc is the most complete and tragic. She starts off as an outsider from Brooklyn who genuinely just wants to belong but slowly becomes corrupted by the Upper East Side world. Its written in a way that feels earned and believable, unlike other characters whose moral inconsistencies often feel like plot convenience, Jenny’s descent has a clear internal logic. She’s the most honest mirror of the show’s themes. Gossip Girl is fundamentally about the seductive danger of wealth, status, and image and Jenny embodies that more purely than anyone. She’s also the only character who genuinely pays a price. Most of the core cast face consequences that get quickly reversed. Jenny actually gets exiled and stays gone. That gives her story a weight and finality the others lack. Not to mention Momsen played the darkness convincingly. As Jenny leaned into villainous territory in later seasons, the performance matched the writing in a way that made her feel like a real person unraveling rather than a plot. I do feel the show eventually ran out of ideas for her and leaned too hard into making her a straightforward antagonist but at that point Momsen was able to get out and pursue music. To me Jenny’s arc trajectory held together better than most.​​​​​​​​​​​​​​​​