Top 10 Most Unhinged Gossip Girl Moments
#10: The Charlie/Ivy/ Lola Drama Various
Top 10 Saddest Gossip Girl Moments
Convoluted plotlines were a “Gossip Girl” speciality, especially in the later seasons. By the time you reach the saga of Ivy Dickens, you’ll need a notebook and pen just to keep track. When we first meet Ivy, she’s being paid by Serena’s aunt Carol to pretend to be her daughter, Charlie. Carol wants access to a trust fund left to Charlie by Grandma CeCe. CeCe uncovers the plot but decides to give Ivy an inheritance anyway. Things only get more complicated once the real Charlie turns up, calling herself Lola. During her tenure in the Upper East side, Ivy also finds time to romance Dan, Nate, and two of Lily’s ex-husbands. It’s as messy as it sounds, and that’s barely half of it!
#9: The Three Person Entanglement “They Shoot Humphreys, Don't They?”
Next to teen dramas like “Euphoria,” the exploits of Manhattan's Upper East Siders can look slightly tame. However, back in the day, “Gossip Girl” was pushing boundaries. Early ads for the show played up reviews that described it as “every parent’s worst nightmare.” Just when we thought the shock value might be wearing off, the writers proved they could still surprise us. The three-person tryst between Dan, Vanessa and Olivia, played by recurring guest star, Hilary Duff, is thrown into season 3, and basically forgotten shortly after. Duff portrays a movie star, but the character is still a girl-next-door type. The move seems rather out of character for everyone involved, and it leads to Olivia and Dan’s breakup, and her exit.
#8: Lily’s Fake Cancer Various
Top 10 Funniest Lily Moments on How I Met Your Mother
Serena’s mom, Lily van der Woodsen, lived through a lot of drama. One of her partners returns from the dead, another is the father of her long-lost child, and one manipulates her into believing she has cancer. Guess who turns out to be end-game? William van der Woodsen, played by William Baldwin, comes back into Lily’s life when she is genuinely ill and at her most vulnerable. He helps her through her recovery but falls in love with her along the way. So naturally, he keeps prescribing her unnecessary medication to convince her she’s still sick. Oh, and he also conspires to break her and Rufus up. What a charmer?
#7: Chuck & Club Victrola “Victor, Victrola”
Top 10 Times Chuck Bass was the Worst on Gossip Girl
Wealth and status can buy you many things, but “Gossip Girl” really challenged our definition of plausibility. Take Chuck Bass, for example. He is basically the definition of privileged and pleasure-loving, it’s true. But why is it presented as normal that he’s trying to convince his dad to invest in an “exclusive” burlesque club? And how does he SUCCEED? Chuck is set up from the beginning as a hedonistic playboy, but we can’t forget he’s younger than he acts. It’s just one in a series of unhinged things he does, but it perfectly embodies how he often lives like a sleazy billionaire enjoying a mid-life crisis. It’s not a cute look, and it makes absolutely no sense.
#6: Dan & Serena Share a Sibling Various
Top 10 Best Serena Moments on Gossip Girl
Returning to Lily and her tangled life, let's talk about Scott Rosson. Who’s that? He’s Lily’s secret love child of course! Biological half-sibling to both Serena and Dan. Scott’s existence was hidden from his father Rufus, until Lily’s mother decided to drop the bombshell after years of silence. When the couple attempt to track down their son, they’re told he passed away. But that turns out to be a lie, because this is “Gossip Girl”! Scott covertly infiltrates their world, only telling his parents who he is at their wedding. He promises to keep in touch, but after season three, we never see him again. It seems he didn’t even get an invite to his own half-siblings’ wedding – to each other – yikes.
#5: Chuck Is Attacked & Ends Up in France Various
When fictional characters experience a traumatic or life-altering event, we don’t want them to snap back to normal right away. However, Chuck Bass’s fresh start in season four is a step too far. At the end of the third season, he’s shot in Prague. He’s rescued by Eva, a.k.a. “Harry Potter” star Clémence Poésy, who whisks him off to Paris. Chuck tells her his name is Henry and decides to settle down and become a hard-working French resident. Did that bullet give him a personality transplant? This is Chuck Bass we’re talking about. His old friends eventually come and rescue him from his respectable new life, but we get worried for a while there.
#4: When Chuck Trades Blair For a Hotel “Inglourious Bassterds”
Looking back, it’s bizarre that we bought into the fairytale romance of Chuck and Blair. There’s being a bad boy, and then there’s trying to trade your girlfriend to your creepy uncle in exchange for a hotel. Chuck tells Jack that he’s prepared to pay any price to get his hotel back – it turns out his uncle is interested in Blair. Unbeknownst to the viewer, Chuck accepts Jack’s indecent proposal. He proceeds to manipulate his girlfriend into offering herself to Jack, without Chuck having to ask her. He knows her so well at this point that he’s confident she’ll do it out of love for him, if he plays his cards a certain way. Nothing ultimately happens between them, but we’ll never forget the betrayal.
#3: Serena, Juliet & Ben Various
Top 10 Serena & Blair Fashion Moments
The big mystery of season four revolves around Juliet Sharp. Who is she, and what did Serena van der Woodsen ever do to her? Juliet’s actions become increasingly unhinged throughout, peaking after she enlists Jenny and Vanessa to really mess with Serena’s head. For her final trick, she incapacitates Serena and abandons her. Turns out, the reason for all this is actually Juliet’s brother Ben, an old teacher of Serena’s. He was jailed for having inappropriate relations with her, thanks to a false accusation. This accusation was made not by Serena, but by, yup, Lily. Of course, once Ben gets out of prison, there’s a whole new set of absurd moments to deal with. To say the whole thing is ridiculously convoluted and wild would be an understatement.
#2: Bart Bass Comes Back From the Dead “Raiders of the Lost Art”
Of all “Gossip Girl’s” deranged twists, the return of Bart Bass is one of the most unbelievable. Chuck’s dad is killed in a car crash in season two, or so we’re made to believe. If we had any doubts, they were removed by his wife’s remarriage and the appearance of his ghost in the following season. Except that ghost must’ve been in Chuck’s head, because we later learn that Bart is very much alive. He’d apparently faked his death to save his family from the wrath of a business rival. We know, it’s madness. Anyway, from then on, Bart is back more wicked than ever – until he dies again – for real, after a vicious battle with his son in the final season.
#1: Dan Is Gossip Girl “New York, I Love You XOXO”
Of all the people “Gossip Girl” could have been, Dan Humphrey is far from the most logical. Sure, she dubs him “the Ultimate Insider” at one point But it still doesn’t add up. Why would he repeatedly stir up drama that places him at a personal disadvantage? Does he enjoy spreading stories about his kid sister? How does he drop a Gossip Girl post while standing on the altar during a royal wedding? And why does he make shocked faces when reading his own updates, alone? In Cecily von Ziegesar’s books, Gossip Girl’s identity is kept secret - and it’s not really relevant. We probably would’ve felt short changed without a big reveal, but Dan? Really? Which bizarre “Gossip Girl” storylines stick in your memory? Share your favorites in the comments!
