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Georgina Sparks
Georgina Sparks is a friend of Serena from her wild days, only she hasn't quite recovered from them. She blackmails Serena, pretends to be someone else entirely, and even tricks Dan into thinking that her half-Russian baby is actually his, forcing him to look after Milo for quite a while. She's a genuinely repulsive person and fans never quite forgave her for the trouble she causes the well-loved characters over the course of the series.
Juliet Sharp
Juliet is a troubled woman who enters the series in season four and causes a world of problems. She manipulates the characters and is unapologetic, going as ruthlessly far as to almost kill Serena. She genuinely doesn't seem to care about other people and because of this, fans have little sympathy for her troubled past.
Dan Humphrey
Dan starts out as one of the least problematic guys. Hailing from Brooklyn, starry-eyed over Serena, he wants to do good by everyone. The last season reveals that he's been Gossip Girl all along, which caused an understandable storm with fans when it was first aired — especially as Dan is so very quickly forgiven by the other characters, leaving the viewers craving revenge that the other characters aren't.
Vanessa Abrams
Vanessa also comes from a place that isn't the Upper East Side, and has very little to do with the riches and scandals of the world that Gossip Girl reports on. Yet she quickly goes in the same direction as Jenny and is also involved in the scenario that has Serena drugged.
Jenny Humphrey
Jenny starts off as one of the purest characters. She's from Brooklyn, with very little to do with the riches and glamor of the Upper East Side.
Yet she quickly gets dragged into the world and becomes as vicious as Blair Waldorf herself, going as far as to get herself involved in a scheme that gets Serena drugged. Still — Jenny objectively isn't the worst character in the series, but there is a definite air that she doesn't belong, so fans tend to latch on harder to her wrong-doings and she gets a harsher time of it than characters such as Blair might.
She also caused problems between the iconic power couple of Blair and Chuck and even though this was mostly Chuck's fault, ship stans weren't happy.
Louis Grimaldi
Louis Grimaldi seems like the ultimate fairy tale prince. He's the answer to all of Blair's romantic questions - until he reveals his true colors to her.
It's an unwritten rule in the Gossip Girl handbook that if you're a character that hurts Blair Waldorf, the audience is going to hold a grudge. His attempt to lock Blair into a loveless marriage and a hostile family is one the audience will never forgive.
Bart Bass
It's often the younger generation of characters that are seen as the most problematic of the Gossip Girl bunch, but Bart Bass is actually the worst. He's easily the most callous and manipulative of the series.
The silver lining is that Bart's behavior, and just how he treats his son, goes a long way to explain just how Chuck becomes who he is as a teenager. As much as fans hate Bart, his presence in the series allows Chuck a little more empathy from the viewers.
Ivy Dickens
When Ivy first joins the series, it's while masquerading as Charlie, an extended member of the Rhodes family, and Serena's cousin. She fits in well enough at first, but once everyone discovers that she was hired to pretend to be Charlie, literally everyone turns on her. Instead of trying to take the high ground, Ivy becomes more and more manipulative.
It's also a little odd to fans that she dates both Dan and Serena's fathers during her attempts to manipulate the Van der Woodsens. That alone was enough to weird fans out since she's the same age as Serena, Blair, and her friends.