10 Of The Craziest Moments From The Original ‘Gossip Girl’ Series

I had mixed feelings about watching the Gossip Girl reboot on HBO Max after showrunner Josh Safran announced that the reboot will involve characters "wrestling with their privilege,” but I still watched it because I’m a sucker for nostalgia. I expected it to be woke and annoying (which it was), but I didn't expect it to be boring (which it was).

The original Gossip Girl was so good because it was so dramatic that it was unbelievable. These characters seemed to be addicted to scandal, and it was hilarious to watch it all play out. Since the reboot is boring, why not break down some of the craziest things that happened on the original show? It was tough to narrow it down because I could probably write a dissertation on this, but here are the 10 craziest moments.

Major spoilers are ahead!

10. The Truth about Serena’s Cousin

In the fourth season, we meet Serena’s cousin Charlie “Lola” Rhodes, daughter of Lily’s sister Carol. She and Serena haven’t spoken since they were in middle school, so it’s fun watching the two catch up. However, this is Gossip Girl, and anything that seems heartwarming is actually malicious. At the end of the third season, we find out that Charlie is actually an aspiring actress named Ivy Dickens, a close friend to Charlie who Carol hired to steal the money in Charlie’s trust fund.

Ivy gives the trust fund money to Carol and moves to Los Angeles to start her acting career, but Serena (who still thinks she’s her cousin Charlie) sees her, dashing Ivy’s hopes of leaving the scheming behind her. The scam comes to an end when she runs away, and Lily hires a private investigator to find Charlie, only to find the real Charlie and get Ivy to admit that she and Carol were in it for the money. 

9. The Real Reason Why Serena Left New York

Serena returns from boarding school in the pilot episode, and we’re led to believe that she left New York because she had sex with Nate while he was dating Blair. While this is already scandalous, we later learn the true reason why she left New York.

Serena spends the majority of the first season cleaning up her party-girl image and succeeds. But she begins to slip back into her old ways when Georgina Sparks, her old partner in crime, returns to town. Georgina blackmails Serena into facing why she left in the first place, which was because she gave cocaine to a man who overdosed. Serena called the ambulance before Georgina convinced her to leave to avoid arrest, but Serena convinced herself she was responsible when she found out the man died. She blamed herself and left for boarding school until the scandal blew over. A year later, her mother takes her to visit the man’s parents to find out that they didn’t blame her for his death, finally clearing Serena’s conscience.

8. Captain Archibald’s Embezzlement Scandal 

Though Nate’s father, Captain Archibald, is a successful businessman and retired naval captain, he runs into financial problems (and a cocaine addiction) during the first season. After the Captain is arrested for cocaine possession in the middle of the first season, it’s revealed that he has also been charged with embezzlement and fraud. He goes to rehab for his cocaine addiction but doesn't want to go to jail for embezzlement and fraud.

In the finale of the first season, Nate learns that his father is planning on fleeing the country to avoid going to jail. He wants Nate and his wife to go with him, but they refuse. At the beginning of the second season, we learn that Archibald's assets are frozen due to the Captain’s disappearance. This leads Nate to live in his family’s city home without any electricity so he can go to school, while his mother extends her summer in the Hamptons. He bounces from the Humphrey’s to Chuck’s before his father returns to New York for Thanksgiving, and Nate convinces the Captain to turn himself in so they can have their normal lives back. Though this storyline is crazy, it’s heartwarming in the end because we see Nate mature and his relationship with his father grow after he turns himself in. 

7. Blair Hazing Her Teacher 

This is probably the funniest one because it shows how crazy the characters in Gossip Girl really are. In the middle of the second season, we’re introduced to Rachel Carr, a Shakespeare teacher at Constance Billard. She develops a close relationship with Serena, but finds her way onto Blair’s bad side when she gives her a B on a paper. It only stresses her out more when she’s waitlisted at Yale.

Blair has never gotten anything less than an A in her life, so she loses her mind when she gets a B. Blair tries to talk to Rachel about it but decides to take matters into her own hands when she refuses to change her grade. She invites Rachel to have dinner with her family before going to an opera, only to give her the address to the wrong restaurant. Blair gets detention for hazing Rachel and is removed from Yale’s waitlist, shattering her dreams of attending her father’s alma mater. This story goes to show how entitled and petty these characters are, and I love it.

6. Rufus and Lily’s Kid

Lily van der Woodsen is such a mess that I can’t help but think she’d be the perfect fit for The Real Housewives of New York City (my favorite Housewives franchise) if she were real, and this storyline shows how messed up she really is. We all know that Lily fell in love with Rufus Humphrey, Dan and Jenny’s dad, when they were younger. They plan to run off together in the middle of the second season, only for Lily’s mother to tell Rufus that Lily had a child when they were together and gave him up for adoption.

Rufus and Lily try to track down their son, but find out that he died in a boating accident. It’s later revealed that their son’s adoptive brother was the one who died and their son, Scott, is still alive. Scott moves to New York to track down his long-lost parents, where he befriends Dan before meeting Rufus. The two develop a close relationship, and Scott meets Lily on the day she marries Rufus. Scott never returns to New York, but it was sweet to watch him meet his biological parents.

5. When Nate’s Cousin Tried To Have Him Killed

All of the families in Gossip Girl are nuts, but Nate’s family takes it to the next level. Aside from the problems on the Archibald side of the family, there are plenty of problems on his mother’s side because she’s a Vanderbilt. Nate’s relationship with his Vanderbilt side is rocky, but nothing was crazier than when his cousin Trip tried to have him killed.

Nate and Trip are feuding because their grandfather favors Nate. In the middle of the fifth season, Nate lets Chuck and Blair take his limo while riding in the car behind him and sees the limo crash. Chuck and Blair survive the crash, but Nate discovers that Trip paid someone to drain the brake fluid in Nate’s limo to try to kill him. I get that Trip was jealous of Nate having their grandfather’s attention, but did he have to try to kill him for it? 

4. Lily’s Fake Cancer 

We all know that Lily has had many husbands, but we rarely get a glimpse into the ones who came before Bart Bass and Rufus Humphrey. In season three, we meet William van der Woodsen, Lily’s first husband and Serena and Eric’s father.

William is a doctor, and we find out that Lily went to see him before she married Rufus because she felt sick. William diagnoses Lily with cancer and treats her in secret. Lily returns to New York when she’s stable and keeps her cancer a secret from her family, but that doesn’t stop William from showing up later in the season. It’s later revealed that William fell in love with her again when she started treatment and never told her she was in remission, but gave her medicine to make it seem like she was still sick so she would rely on him. We usually expect scheming from the younger characters, but the older generation of the van der Woodsens have a knack for it too.

3. Chuck Getting Shot in Prague

Chuck cheating on Blair with Jenny at the end of the third season was already scandalous, but what happened afterward is even more shocking. When Blair finds out, she banishes Jenny from Manhattan and breaks up with Chuck. A heartbroken Chuck travels to Prague after the breakup, and the season ends with Chuck getting mugged and shot in the middle of the street, leaving viewers wondering if Gossip Girl killed off one of its most beloved characters. Luckily, Chuck survives and continues to be one of the most memorable characters on the show for the rest of the series.

2. When Bart Bass Came Back to Life AND Tried To Kill His Own Son

This is one of my all-time favorite twists because it’s absolutely bonkers. Chuck spends the first season and a half trying to impress his billionaire father, only for his father to die in a car accident halfway through the second season. Chuck has a hard time coping with his passing and works hard to make his father proud when he inherits his business.

At the end of the fifth season, Chuck discovers that his dad faked his own death to protect his family from a business rival who wanted to kill him. Though the majority of Gossip Girl characters are morally questionable at best (and we love that for them), we learn that Bart is beyond questionable – he’s actually evil. He takes his business back from Chuck when he returns from hiding, and Chuck learns that his father had been involved in some shady business deals in the past. Chuck tries to expose his father so he can earn his business back, and Bart tries to have his own son killed to stay in power. The power struggle ends near the end of the sixth (and final) season when Bart dies after falling off a building. Chuck wins the business back in the series finale, (finally) marries Blair, and they all live happily ever after.

1. Finding Out Who Gossip Girl Is 

We spend the entire show wondering who’s behind the Gossip Girl blog. We think it’s Georgina at one point, but she only hijacked the blog after it got shut down. We all sat on the edge of our seats during the series finale to find out who Gossip Girl was, only to find out that it was Dan Humphrey.

I have mixed feelings. I’m a firm believer that it should have been Dorota because that made the most sense and would have been hilarious. Dan being Gossip Girl does align with him being shady, and the fact that it was one of the main characters all along makes it even more shocking and scandalous. The only thing I didn’t like about it was that Serena forgave Dan and eventually married him. Serena should have dumped Dan and married Nate, and that’s a hill I’m willing to die on.

Closing Thoughts

The new Gossip Girl may be boring, but that can’t stop us from re-watching the original show in all of its over-dramatic glory. From hazing teachers to faking deaths, the original Gossip Girl has cemented itself as one of the greatest teen drama shows of all time.

Love Evie? Let us know what you love and what else you want to see from us in the official Evie reader survey.