Few shows did unhinged like "Gossip Girl." Welcome to MsMojo, and today we’re counting down our picks for the wildest and most convoluted storylines from the original “Gossip Girl” series.
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00:00 Hey Upper East Siders, Gossip Girl here and I have the biggest news ever.
00:06 Welcome to Ms. Mojo and today we're counting down our picks for the wildest and most convoluted storylines from the original Gossip Girl series.
00:15 Plot points will be discussed, so beware of spoilers.
00:19 Even if I didn't have the police commissioner in my pocket, who do you think they're gonna believe? Huh?
00:26 10. The Charlie/Ivy Lola Drama - Various
00:30 Convoluted plotlines were a Gossip Girl specialty, especially in the later seasons.
00:35 By the time you reach the saga of Ivy Dickens, you'll need a notebook and a pen just to keep track.
00:41 When we first meet Ivy, she's being paid by Serena's Aunt Carol to pretend to be her daughter Charlie.
00:52 Carol wants access to a trust fund left to Charlie by Grandma Cece.
00:56 Cece uncovers the plot, but decides to give Ivy an inheritance anyway.
01:11 Things only get more complicated once the real Charlie turns up, calling herself Lola.
01:16 During her tenure in the Upper East Side, Ivy also finds time to romance Dan, Nate and two of Lily's ex-husbands.
01:23 It's as messy as it sounds, and that's barely half of it.
01:27 9. The Three-Person Entanglement - They shoot Humphreys, don't they?
01:36 Next to teen dramas like Euphoria, the exploits of Manhattan's Upper East Siders can look slightly tame.
01:43 However, back in the day, Gossip Girl was pushing boundaries.
01:47 Early ads for the show played up reviews that described it as "every parent's worst nightmare."
01:59 Just when we thought the shock value might be wearing off, the writers proved they could still surprise us.
02:06 "That one."
02:08 "Have you ever heard of it?"
02:12 "No, no, no, never."
02:14 The three-person tryst between Dan, Vanessa and Olivia, played by recurring guest star Hilary Duff, is thrown into season three.
02:21 And basically forgotten shortly after, Duff portrays a movie star, but the character is still a girl-next-door type.
02:28 The move seems rather out of character for everyone involved, and it leads to Olivia and Dan's breakup, and her exit.
02:35 "So much for the ultimate college experience."
02:37 "What? No, I have had the ultimate experience. With you guys."
02:42 8. Lily's Fake Cancer - Various
02:46 Serena's mom, Lily Vanderwoodsen, lived through a lot of drama.
02:50 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.
02:57 Guess who turns out to be endgame?
03:00 "Oh, God. William."
03:02 "Dad?"
03:04 William Vanderwoodsen, played by William Baldwin, comes back into Lily's life when she is genuinely ill, and at her most vulnerable.
03:12 He helps her through her recovery, but falls in love with her along the way.
03:17 "I made the biggest mistake of my life walking out on you, and I promise to do everything in my power to make it up to you, to make it right again."
03:26 So, naturally, he keeps prescribing her unnecessary medication to convince her she's still sick.
03:32 Oh, and he also conspires to break her and Rufus up.
03:35 "I'm getting exactly what I wanted, to be with Lily. The love of my life, the mother of my children, and I thank you.
03:42 I truly thank you for the role you played in making that possible."
03:47 What a charmer.
03:48 7. Chuck and Club Victrola - Victor Victrola
03:53 Wealth and status can buy you many things, but Gossip Girl really challenged our definition of plausibility.
04:00 Take Chuck Bass, for example.
04:02 "Long night?"
04:03 "Alfonso made me an omelet. I may have washed it down with a bellini or two."
04:09 He is basically the definition of privileged and pleasure-loving, it's true.
04:13 But why is it presented as normal that he's trying to convince his dad to invest in an exclusive burlesque club?
04:21 And how does he succeed?
04:23 "I am so pleased."
04:25 "You are?"
04:27 "Are you kidding me? Do you know how long I've been waiting for you to be interested in something other than partying?"
04:33 Chuck is set up from the beginning as a hedonistic playboy, but we can't forget he's younger than he acts.
04:39 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 midlife crisis.
04:49 It's not a cute look, and it makes absolutely no sense.
04:53 "I'm Chuck Bass."
04:56 Number 6. Dan and Serena share a sibling. Various.
05:02 Returning to Lily and her tangled life, let's talk about Scott Rawson.
05:07 Who's that? He's Lily's secret love child, of course.
05:10 Biological half-sibling to both Serena and Dan.
05:14 "Oh, uh, our dad dated your mom."
05:16 "Yeah, we're not related though."
05:17 "What?"
05:18 "We're not even broods."
05:19 "Wait, wait, what?"
05:21 Scott's existence was hidden from his father Rufus, until Lily's mother decided to drop the bombshell after years of silence.
05:29 When the couple attempted to track down their son, they're told he passed away.
05:33 But that turns out to be a lie, because this is Gossip Girl.
05:36 "That was..."
05:37 "Your love child."
05:38 "Yeah."
05:39 "Not dead."
05:40 "Congratulations, it's a boy."
05:41 Scott covertly infiltrates their world, only telling his parents who he is at their wedding.
05:46 He promises to keep in touch, but after season 3, we never see him again.
05:51 It seems like he didn't get an invite to his own half-sibling's wedding to each other. Yikes.
05:56 "Oh, no, no, no, I'm gonna faint."
05:58 "To repeat, we are not related."
06:00 "She was a groupie, and he was almost famous."
06:02 "Suddenly my family seems so sane."
06:04 Number 5. Chuck is attacked and ends up in France. Various.
06:09 When fictional characters experience a traumatic or life-altering event, we don't want them to snap back to normal right away.
06:17 However, Chuck Bass' fresh start in season 4 is a step too far.
06:21 "I'm really sorry to show up like this. I've just been looking for Chuck everywhere."
06:26 "I don't know who she's talking about."
06:28 "I don't know. The man you're looking for is not here."
06:31 At the end of the third season, he's shot in Prague.
06:35 He's rescued by Ava, aka Harry Potter star Clemence Poesy, who whisks him off to Paris.
06:41 Chuck tells her his name is Henry and decides to settle down and become a hard-working French resident.
06:47 "I suppose it's worth missing you if it means staying in a place where you don't have nightmares."
06:52 "And you look very handsome in your work clothes."
06:56 "Well, I look forward to you removing them after an honest day's work."
07:01 Did that poet give him a personality transplant?
07:04 This is Chuck Bass we're talking about.
07:06 His old friends eventually come and rescue him from his respectable new life, but we got worried for a while there.
07:13 "After today, there is no Chuck Bass."
07:16 "I'm staying at Eleanor and Cyrus's when you realize that's not true."
07:20 Looking back, it's bizarre that we were brought into the fairy tale romance of Chuck and Blair.
07:30 There's being a bad boy, and then there's trying to trade your girlfriend to your creepy uncle in exchange for a hotel.
07:36 "Oh, what are you talking about? Chuck doesn't know anything about this."
07:40 "Really? Because it seems to me he knew exactly which buttons to have me push."
07:45 Chuck tells Jack that he's prepared to pay any price to get his hotel back.
07:49 It turns out his uncle is interested in Blair.
07:52 Unbeknownst to the viewer, Chuck accepts Jack's indecent proposal.
07:57 He proceeds to manipulate his girlfriend into offering herself to Jack without Chuck having to ask her.
08:03 "If I asked, it wouldn't have worked. He would have been too willing when Jack came to you. He would have known we were working together."
08:10 "I did what I had to, to win."
08:13 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.
08:20 Nothing ultimately happens between them, but we'll never forget the betrayal.
08:24 "You said you would stand by me through anything. This Blair is anything."
08:31 "I never thought that the worst thing you would ever do would be to me."
08:35 Number 3. Serena, Juliet and Ben. Various.
08:39 The big mystery of season 4 revolves around Juliet Sharp.
08:43 Who is she, and what did Serena Van Der Woodsen ever do to her?
08:47 "Oh, come on. Don't you think you're going a little far to hold on a date?"
08:50 "What are you talking about?"
08:51 Juliet's actions become increasingly unhinged throughout, peaking after she enlists Jenny and Vanessa to really mess with Serena's head.
08:59 For her final trick, she incapacitates Serena and abandons her.
09:04 "I don't know where I am or how I got here. Please help."
09:10 Turns out, the reason for all of this is actually Juliet's brother Ben, an old teacher of Serena's.
09:16 He was jailed for having inappropriate relations with her, thanks to a false accusation.
09:21 This accusation was made not by Serena, but by, yep, Lily.
09:26 Of course, once Ben gets out of prison, there's a whole new set of absurd moments to deal with.
09:31 To say the whole thing is ridiculously convoluted and wild would be an understatement.
09:36 "How are you going to say that?"
09:38 "Because it's the truth. And you don't see it, but you're caught in a trap."
09:43 Number 2. Bart Bass comes back from the dead.
09:46 Raiders of the Lost Art
09:48 "Death. Oh my God."
09:52 Of all Gossip Girl's deranged twists, the return of Bart Bass is one of the most unbelievable.
10:00 Chuck's dad is killed in a car crash in season 2, or so we were made to believe.
10:05 If we had any doubts, they were removed by his wife's remarriage and the appearance of his ghost in the following season.
10:12 "No disrespect, but I don't need your advice. I've been doing pretty well without you."
10:19 "Oh yeah."
10:23 Except that ghost must have been in Chuck's head, because we later learn that Bart is very much alive.
10:29 He'd apparently faked his death to save his family from the wrath of a business rival.
10:34 We know, it's madness.
10:36 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.
10:46 "Give me your hand. You know I'm all talk. I would never really hurt you. Everything you say is a lie."
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11:10 Of all the people Gossip Girl could have been, Dan Humphrey is far from the most logical.
11:29 Sure, she dubs him as the ultimate insider at one point, but it still doesn't add up.
11:34 Why would he repeatedly stir up drama that places him at a personal disadvantage?
11:39 Does he enjoy spreading stories about his kid sister?
11:42 "Jenny wanted to get on Gossip Girl. She's known it was me for years. If there's ever anything she really didn't want posted, all she had to do was ask."
11:49 "You told the whole world about her losing her virginity."
11:52 "No, she sent that tip in herself."
11:54 How does he drop a Gossip Girl post while standing on the altar during a royal wedding?
11:59 And why does he make shocked faces when reading his own updates alone?
12:03 In Cecily Vonzigeiser's books, Gossip Girl's identity is kept secret, and it's not really relevant.
12:09 We probably would have felt shortchanged without a big reveal, but Dan? Really?
12:15 "Oh, you have got to be kidding me."
12:17 Which bizarre Gossip Girl storylines stick in your memory?
12:20 Share your favorites in the comments.
12:23 "I am Serena's daddy, Doctor."
12:25 "Didn't see that one coming."
12:27 Do you agree with our picks? Check out this other recent clip from Ms. Mojo.
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12:35 [music]