The best part of Gossip Girl was seeing our favorite characters triumph over adversity and hard times. They had to overcome drama with quite a few villains between season 1 and season 6. The characters of Serena van der Woodsen, Blair Waldorf, Dan Humphrey, Chuck Bass, and Nate Archibald always came out on top regardless of who they were facing off against.
Blake Lively, Leighton Meester, Ed Westwick, and Chace Crawford are the actors behind the leading roles and each of them did an excellent job in Gossip Girl during the early 2000s. Let's also not forget about Penn Badgley who has moved on to star in Netflix's YOU. A reunion movie or episode would be so amazing if everyone were to jump on board! Here is how the villains of the show rank in order from least horrible to absolutely evil.
10 Agnes Andrews - The Jealous And Devious Model
Agnes Andrews was a jealous and conniving model who was willing to sabotage Jenny Humphrey. She convinced Jenny to get drunk before an important appointment, set Jenny's dresses on fire in a trash can, and eventually drugged Jenny with illegal substances.
Before all that, she nearly convinced Jenny to strip down in front of a photographer! Agnes Andrews was bad news on every level and it was a relief to finally see her character get written off the show. All she did was mess with Jenny!
9 Asher Hornsby - The Guy Who Used Jenny As A Beard
Asher Hornsby is another character from Gossip Girl who negatively impacted Jenny Humphrey's life. He convinced her that he had feelings for her when in reality, he was actually hiding the fact that he had a boyfriend.
He was secretly dating Eric van der Woodsen and did not want the world to know. Instead of embracing his identity, he used Jenny to be his fake girlfriend. She ended up getting her feelings hurt over him because she thought he really liked her.
8 Tripp Van Der Bilt - He Left Serena For Dead
Tripp van der Bilt is a trash individual. First of all, he cheated on his wife with a girl who was barely 18 years old. That's strike one! Second of all, he was constantly competing with his own cousin, Nate, for the attention and affections of their grandfather.
Third of all, he got into a car accident with Serena van der Woodsen in the car and he left her for dead! Three strikes and you are out. He is one of the worst characters from the entire show.
7 Diana Payne - She Lied About Being Chuck's Mother
Diane Payne was beyond annoying in every way. Her manipulation of Nate Archibald was cringe-worthy, to say the least. She was trying to control him with intimacy and it was gross. Nate needed to be spending time with a woman closer to his own age who wasn't so power-hungry.
She also lied about being Chuck Bass' birth mother which caused a whole lot of confusion. It was super weird and random but it turned out she was paid off to lie about it. Anyone who accepts money to lie to other people is a villain... Diane Payne is no exception!
6 Louis Grimaldi - He Tried To Trap Blair In A Loveless Marriage
Louis Grimaldi didn't start off evil. He changed at his wedding with Blair. He pretty much whispered into her ear that she would be trapped in a loveless marriage with him and that she would be forced to follow all of his family's rules. He was bitter upon finding out that Blair was in love with Chuck, still.
Blair immediately ran away to get free from him, which was the smartest thing she could have done. Louis Grimaldi didn't even consider forgiving her for her transgressions, he just wanted to punish her. It seems like he never really loved her at all.
5 Poppy Lifton - She Tried To Scam Serena
Poppy Lifton was a socialite who pretended to be way wealthier and well-traveled than she was. She fronted herself off as if she was on Paris Hilton's level. She was nothing more than a scam artist who pulled Serena van der Woodsen into her web by pretending to be friends with her.
Serena has a big heart and is naturally very kind to others. It wasn't much of a challenge for Poppy Lifton to trick Serena. Poppy also somehow manipulated Serena into thinking she wasn't cool enough and that made Serena want to impress Poppy even more.
4 Gabriel Edwards - He Also Tried To Scam Serena
Just like Poppy Lifton, Gabriel Edwards was a scam artist who tricked Serena van der Woodsen. He also tricked her family and friends. Worst of all, he tricked Rufus Humphrey out of his life savings.
Lily van der Woodsen had to then step up to help Rufus out financially even though he did not want a handout. Gabriel Edwards was a super evil and conniving jerk. He made Serena think he was falling in love with her when in reality he just wanted to steal money. She had no business dating this guy... everyone knows Serena was meant to end up with Dan Humphrey.
3 Juliet Sharp - She Started Rumors About Serena
Juliet Sharp set out to get revenge against Serena van der Woodsen because her brother was locked up in prison for a crime he never committed. The court system blamed him for hooking up with Serena when she was underage. That never happened!
Serena found out the truth and made sure that he was released from jail. Prior to all that, Juliet Sharp spread some nasty rumors about Serena around the school campus and did her best to try and sabotage Serena's entire life. Katie Cassidy is the actress behind the role of Juliet Sharp. She is also part of the Arrowverse.
2 Georgina Sparks - The Crazy Blackmail Queen
Georgina Sparks was one of the most messed up characters from Gossip Girl. She drugged and sabotaged Serena van der Woodsen the day Serena was supposed to take her SAT. She also blackmailed Serena with footage of illegal activity that led to a guy's overdose on illegal substances... footage that included Serena!
Georgina tried to convince Dan Humphrey that she was pregnant with his baby and once she gave birth, she left the baby with Dan to care for even though it wasn't actually his kid!
1 Bart Bass - A Pure Evil Man Who Tried To Kill Chuck
The evilest villain from Gossip Girl is easily Bart Bass. He tried to kill his own son, Chuck Bass. Need we say more? He also faked his own death which stirred up a whole lot of drama. When he finally resurfaced and revealed that he was never actually dead, it turned Chuck's life upside down.
Chuck had already reformed and was starting to be a better person by the time his dad returned. The scene where Bart tried to kill Chuck is still very haunting and dramatic to watch.