Still from Gossip Girl 1×13 featuring Taylor Momsen as Jenny Humphrey. Image via The CW.
Jenny Humphrey – Gossip Girl
Jenny Humphrey wasn’t always the bratty, opportunistic mean girl she turned out to be. In the early seasons I found her quite delightful. As the cutesy kid sister to the ever-morose Dan, she was a breath of fresh whimsy, with her big dreams and desire to fit in.
Jenny’s main problem was finding herself in situations that she absolutely shouldn’t have been in the first place, had she shown even a glimmer of forethought. She bowled her way through some pretty heavy circumstances (remember when she was a drug mule?), and didn’t really seem concerned with any sort of consequences until things went so awry that she was confronted with the devastation head on. She’d run home to cry to her family, and it always seemed like she might have learned her lesson, but she never did.
Over and over, Jenny put herself, her family, and her close friends in jeopardy, and didn’t really seem all that sorry. She finally made the decision, when Taylor Momsen just couldn’t with Gossip Girl anymore, to leave the Upper East Side forever. Good riddance to bad rubbish, if you ask me.
In her defense, Jenny’s bad behavior wasn’t as cutthroat as her brother, Dan’s. Instead of being outright malicious like he was, she was just selfish. She mostly did things to serve her own interests.