The cast of Gossip Girl have done some pretty awful things throughout their six seasons of run time. Pretty much everyone has been "the bad guy" at one point or another, as everyone has done something truly terrible. While most of these awful things (like sleeping with your best friend's boyfriend or telling the world that your best friend is a drug addict when she isn't)were just about petty revenge, a lot of the things the characters did in Gossip Girl were downright illegal.
To watch this series, fans must suspend disbelief pretty often. They must watch and just accept all of the weird and bizarre things that happen to these rich New York City teens. Throughout the first few seasons of the show, fans should try to forget that all of the main characters are still underage, because- quite frankly- none of them act like it. Because the moment a viewer realizes all of the crazy things Serena, Dan, Blair, Chuck, Nate, and everyone else has done, they will also realize that everyone probably should have been in jail before the series even started.
10 Serena & Pete
For a while, Serena genuinely believed that she killed a man, which was why she initially went on the run (to a boarding school in Connecticut, oh so far away) just before the beginning of the series. Pete died after taking a large hit of cocaine while shooting a sex tape with Serena, filmed by Georgina.
In her state, Serena somehow believed that she murdered him and blamed herself for his death. While she wasn't the direct cause, the amount of their drug use and what they had on them, and attempt to shoot an underage sex video, should have resulted in both her and Georgina's arrest. Not to mention that they would probably be tried with third-degree murder for accidental manslaughter, even though the show tries to make it clear that "it wasn't actually Serena's fault."
9 Juliet Drugs Serena
Juliet is a mess of character. Not only is her arrival one of the series's most annoying plotlines, she also caused a ton havoc in her short time around the Upper East Side. Juliet believes that Serena is the reason why her older brother is in jail. Which, she kind of is.
Ben was Serena's teacher while Serena was definitely underage. The two had a thing for each other, but Ben rejected Serena's advances because of her age and their standing. While nothing happened between the two, Lily (Serena's mother) still accused Ben of statutory rape, landing him not only in jail, but also on the sex offender's list. In attempt to get revenge for her brother, Juliet drugs Serena and makes it appear as though Serena "needs help."
8 Vanessa Was Her Accomplice
Vanessa was Juliet's accomplice and willingly aided in the drugging of Serena to try to get back at her for all the headaches she has caused Dan over the years. Juliet, Vanessa, and Jenny all join together to try and take Blair and Serena down. Jenny realizes just how twisted Juliet is, but Vanessa jumps in and tells first. Not because she actually cares about Serena, but because she wants to preserve her own image. Also, she blames it all on Jenny.
Eventually the whole truth comes out, and considering everyone knows that Juliet illegally drugged Serena and that Vanessa helped, the two should definitely be spending their next few years behind bars.
7 All The Teachers Who Kissed Serena (& Dan)
Ben wasn't the only teacher who had the hots for his student. Throughout the six seasons of Gossip Girl, it became almost a trend that Serena wanted to date her teachers. She definitely had a type.
While Ben was the only one she had eyes on when she was underage, her college professors and way-older boyfriends should have definitely been punished to some degree. She even officially dates Ben again once he is out of jail, which is insane. Dan also dates a teacher at one point, while still in high school, in a rather bizarre twist.
6 Chuck Bass For Being Chuck Bass
Chuck Bass has done a lot of bad throughout his time in Gossip Girl, probably worse than most other characters in fact. He is one of the few characters that should probably just go to jail because of all the atrocities he has committed.
From attempting to rape Jenny, to actually having sex with her while she is still underage (she ranged from age 14-17 throughout the whole series). Chuck also got aggressive with Blair once when she refused to "belong" to him, and he sold her to his uncle. He also allows his father to die (which fans unsurprisingly all rooted for) by not helping him when he hung off the side of a building, which they end up not getting blamed for at all and are free to live their "happily ever after."
5 Dan Humphrey For Stalking
Dan Humphrey was stalking everyone throughout the series and releasing gossip about them left and right, creating even more chaos for the teens of the Upper East Side. This, of course, is mostly revealed once everyone discovers that Dan has actually been Gossip Girl all along.
From the beginning of the series, he had been stalking Blair, Serena, and everyone else just to get a good story for his website. Dan Humphrey definitely should have been arrested after the reveal that he had been stalking, defaming, and tormenting these characters for so many years, but instead everyone just forgives him and he marries the girl he had been pining for.
4 Georgina Sparks
Georgina Sparks is another amazing part of this series that often just causes more headache to any given situation she is involved in, but that is part of what makes her so incredibly fun. Throughout the years, even before the series began, Georgina caused a lot of chaos, both legal and illegal.
With just her first appearance on the show, she managed to drug Serena when she was only 16 years old while at a club together so that Serena could "loosen up a little." But beyond drugging her, Georgina was also involved in the death of Pete, and later lied countless times and did a whole bunch of crazy things just for the sake of stirring the pot.
3 Lily Sending An Innocent Man To Jail
Lily van der Woodsen is a weird character for many fans. And while she was a likeable mother figure who truly was just trying to keep her wild daughter in check (and to be fair, Serena is kind of the worst), she kind of loses her way as the seasons begin to drag.
It is revealed that Lily has wrongfully accused and sent an innocent man to jail to get her daughter into a good school. Lily's crimes are eventually revealed, but instead of going to actual jail, she is just placed on house arrest.
2 Underage Drinking & Sneaking Into Clubs
Everyone in this show is underage for the main duration of the series. Little J is underage the entire time, while Blair and Serena don't turn 18 until season two, and don't turn 21 until the last season.
So it is totally bizarre that they are constantly able to drink and get into so many clubs and do whatever craziness they want throughout New York City. While these offenses don't usually warrant arrest, the amount of times these characters do so, and get into trouble for doing so, should have at least had them locked up at the Ostroff Center.
1 Bart Bass
Bart Bass was probably the "main antagonist" of the series, even though he pretended to be dead for more than half of it. But unlike every other character who jumped between good and evil, Bart seemed to always be bad.
He did a number of shady and awful things before his fake death, and after he returned, he was even worse. He tried to kill his son in a staged plane accident and wasn't immediately arrested. But instead of being sent to jail, Bart fell to his death from the top of a New York City building.
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January 07, 2021 at 04:30AM
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Gossip Girl: 10 Times The Main Characters Should Probably Have Gone To Jail - Screen Rant
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