Gossip Girl was one of those shows where virtually every character, at one point or another, did something so reprehensible that it made you think you’d hate them forever. And that’s exactly why you loved them. After all, flawed characters are the best kind. So, here it is: the definitive ranking of the horrible but lovable Gossip Girl characters.
9. Dan Humphrey
Dan’s fall from grace was rough. He started out as Lonely Boy: the outcast kid from Brooklyn, in love with a girl who he thought would never notice him, desperately wanting to fit in. Every time the “different worlds” issue tore Serena and Dan’s relationship apart, we all rooted for him to get the girl again. It seemed like all of Dan’s problems would be solved by moving into the van der Woodsen’s Upper East Side penthouse when Rufus married Lily, despite the fact that the girl he so desperately wanted was now his step-sister, but all it really did was create a monster. Suddenly, not only was Dan still an outsider, but now he lived right in the middle of all of the people who didn’t want him there. Clawing his way into the world of Manhattan’s elite stripped Dan of his down-to-earth Humphrey roots, and left no trace of the Lonely Boy from the pilot. Holding in the secret that he was Gossip Girl for six years probably ate away at the innocent kid we all knew and loved, but that’s really not an excuse because that reveal made absolutely no sense.
8. Vanessa Abrams
Vanessa started out a little shaky with the whole “oh hey, I’m on your fire escape” phone call, and it just went downhill from there. She had a brief period of normalcy when she dated Nate, but she usually had a serious chip on her shoulder when it came to the Upper East Siders. It seemed like deep down, Vanessa believed that all of the crazy things she did were in Dan’s best interest, but really, they were just crazy. Trying to protect your best friend from a world that might eat them alive is one thing, but teaming up with a vengeance-obsessed girl who wants to destroy your best friend’s step-family, just to get him back to the old neighborhood, is a whole other level. You can’t help but feel a little bad for Vanessa for constantly getting sucked into other people’s ridiculous plots, but honestly, she should have had the whole concept of ulterior motives figured out a long time ago. It’s probably a good thing she moved to Spain when she did.
7. Jenny Humphrey
The poor, unsuspecting kids from Brooklyn did not fare well on this show. Jenny did some pretty horrible things in her short three and a half years on Gossip Girl (remember when she was a drug mule?), and the only thing that saved her from a fate worse than her brother’s was that she finally left the city for good during the fourth season (also known as “Taylor Momsen just didn’t want to anymore”). The strange, and kind of annoying, thing about Jenny was that she repeatedly found herself in situations she shouldn’t have been in, and didn’t have a care in the world until they blew up in her face. Little J’s life was just one big cycle of doing something to alienate her family, a glimmer of hope where it seemed like she’d come to her senses, and a crash landing back into disappointing poor, poor Rufus. Every time her life went up in flames (literally, once) and she’d come home crying to her family, we’d all hope she’d finally wipe off all that makeup and hole up in Brooklyn with her sewing machine until college. The remorse that Jenny showed over hurting her family was always that little piece of Brooklyn that she was able to hold onto shining through. While neither of the Humphrey kids adjusted to life on the Upper East Side very well, Jenny’s tailspin straight into Hudson seemed far less calculated than her brother’s stunts.
6. Blair Waldorf
Blair actually and legitimately ruined people’s lives. There’s really no way to put that lightly. Granted, she didn’t ruin everyone’s life, but there were a handful of people who would never be the same after crossing Queen B. Usually, the people Blair destroyed had at least a little of it coming, but it was kind of frightening how easily she was able to get a teacher fired for having a fake inappropriate relationship with a student, all with a smile on her face and a perfectly arranged headband in her hair. Like almost every other character on Gossip Girl, Blair was fiercely loyal to her friends and family, and would stop at no ends to bring down someone who had hurt them. Things got a little dicey when she’d decide that a friend (read: Serena) was a nemesis, but, they’d inevitably somehow get over it, even after Blair did something extra horrible like telling the Dean of Admissions at Yale that Serena was a murderer. It’s best to just not even try to understand the logic on this show.
5. Lily Rhodes-van der Woodsen-Bass-Humphrey
Lily made some seriously questionable, sometimes unethical, and occasionally downright illegal decisions, but she always did what she thought was best for her family. Having your own daughter arrested because you’re mad at her doesn’t exactly seem like it’s in her best interest, but to each his own. Lily may not have had the best judgement (Exhibit A: forging Serena’s signature and winding up on house arrest), but, in her defense, her family didn’t exactly make her life any easier. Considering everyone related to her—through blood, marriage, or secret adoption—was constantly scheming and lying, she probably did the best she could. Seriously though, can somebody check the record for the greatest number of name changes in a television series? Lily’s got to have that one in the bag.
4. Serena van der Woodsen
For someone who was determined to turn her life around and be a better person, Serena sure had a knack for making the worst decisions ever. The really interesting thing about it was that she never seemed to see how terrible some of her ideas actually were. Usually, Serena would come up with some harebrained idea, someone would tell her exactly how horrible that idea was, and then she’d just do it anyways, somehow deciding that nothing would go wrong… because all of her previous bad ideas obviously turned out great. Sleeping with your best friend’s boyfriend? Shouldn’t be a problem. Sleeping with a married congressman? Sounds like a great plan. Dating a professor without actually dating him? Come to think of it, there may be a pattern here.
3. Rufus Humphrey
For almost the entire series, Rufus was a pretty great guy. He sacrificed a (moderately) successful career in music to be home with his family while his kids grew up, and then worked his butt off to send them to elite Manhattan prep schools. He was always there to supply his family, friends, and really anybody who showed up, with an endless supply of waffles. When Dan and Jenny were spinning out of control, he was their moral compass. He waited twenty years and countless marriages to finally be with Lily. He was the one genuinely good character on the show. And then he moved in with the psycho girl who stole his family’s money and pretended to be his step-niece. Rufus was the TV equivalent of an Olympic runner who’s in first place the entire race and then trips and falls on their face five yards before the finish line.
2. Chuck Bass
If there was ever a Most Improved award for TV characters, Chuck Bass would win it. When Gossip Girl started, he was the absolute worst. Not in a “guy you love to hate” way, but in a “guy you legitimately hate” way. He was entitled, spoiled, and wore the weirdest clothes to play basketball. And then he fell in love with Blair. Suddenly, he was putting effort into something, besides finding drugs and girls, for the first time in his life. After Bart Bass died, all Chuck wanted was to be better than his father thought he was, and he did everything he could to get there. The old Chuck reared his ugly head every once in a while to do horrible things like try to trade Blair to his uncle in exchange for his hotel back, but by the end of the series, he was willing to give up everything to get Blair out of her extra screwed up marriage to a Prince. Why? Because he’s Chuck Bass.
1. Nate Archibald
Like Serena, Nate had a serious issue with inappropriate relationships. But, besides a youthful indiscretion with Serena (shocker), he had surprisingly selfless and noble, albeit misguided, reasons for having these relationships. When his father fled the country to avoid jail time for embezzlement charges and the family bank accounts were frozen, Nate gave up his relationship with Vanessa to carry on with a British duchess who agreed to give his family money. While prostitution isn’t exactly the best solution to a problem, Nate did what he thought was necessary to keep his family from going through anymore public embarrassment. After he went to college, he wanted to do something to make his own success without the help of any of his many corrupt family members, especially his grandfather. So, once again, Nate continued on with another unseemly relationship with the owner of the newspaper he worked for to try to make it in the business, which, surprisingly, actually worked. Sure, Nate did some ill-advised things, but unlike his family and friends, he did them for all the right reasons.
Obviously this isn’t an extensive list, and there are plenty more characters of questionable morals where these came from. Feel free to discuss in the comments below. After all, if Gossip Girl taught us anything, it’s that you’re nobody until you’re talked about.
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