‘Gossip Girl’s’ Most Memorable OMG Moments

by | December 17, 2012 at 11:25 AM | Gossip Girl

Leighton Meester and Ed Westwick from the Series Finale of 'Gossip Girl' (Photo: The CW)

Six years ago when “Gossip Girl” debuted, the economy was booming, the “one percent” were celebrated, and every twentysomething blogger fell for the smart, funny show that portrayed teen life as brutal social warfare. Some critics were not sure what to make of the series’ frank depiction of sexuality and drug use. The Parents Television Council complained, and The CW wisely made the pearl-clutching bad reviews the centerpiece of its infamous “OMFG” promotional campaign. It worked.

In its second season, the show’s ratings rose. Unfortunately, “Gossip Girl” lost some of its mojo when the characters graduated high school. Though Serena, Dan, Blair, Chuck and the rest of the gang are still as outrageous as ever, it’s hard to be shocked by the antics of twentysomething characters with improbably high-powered careers. On Monday night, the show bids farewell with a two-hour finale episode that promises to reveal many long-gestating secrets, including the identity of Gossip Girl herself. Before you say XOXO one last time, take a look back at some of the show’s most memorable OMG moments.

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The Original Nate-Serena Hook-Up (“The Pilot Episode”)

The show proved it would go where other teen shows feared to tread in the pilot. Lots of series portrayed underage drinking. “Gossip Girl “celebrated and glamorized it. While the original “Beverly Hills, 90210” took pains to establish that its rich kids, deep down, were not so different from ordinary teens, “Gossip Girl” wanted you to know that the “one percent” were not like you – they were much, much better. They could easily gain access to bars and clubs. They wore couture. They had the social sophistication of 30 year olds. No scene made that clearer than the flashback of Serena (Blake Lively) and Nate (Chace Crawford) having drunken bar sex at a wedding. Other teen shows were about losing your virginity. The only significance here was that Serena slept with her best friend’s boyfriend.

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The Constance Choir Sings Glamorous (Season 1, Episode 3, “Poison Ivy”)

The show established that it was capable of being a sophisticated social satire in its third episode when, long before “Glee” hit the airwaves, the prim and proper Constance Billard choir sang Fergie’s “Glamorous” a cappella in the school’s chapel as the backdrop to the main characters’ arrival at school for the day. This stylized scene, that had nothing to do with any of the episode’s storylines, showed that the then-brand new series was aiming to be more than just an East Coast version of “The O.C.” It may have even helped inspire shows like “Glee” and “Suburgatory.”

Blair Loses Her Virginity to Chuck (Season 1, Episode 7, “Victor/Victrola”) [Note: Her strip tease is the most outrageous part]

It was the scene that launched the show’s signature ship. For the first half dozen episodes of “Gossip Girl,” Blair (Leighton Meester) pined for the perfect, preppy Nate, unaware that he cheated on her with her BFF/sworn enemy Serena. When the truth finally came out, the ultra-uptight Blair responded as any heartbroken teenager would: She joined her nemesis Chuck (Ed Westwick) at an underground speakeasy, Victrola, took the stage, and stripped down to her lingerie. Then she followed it up by losing her virginity to Chuck in a limo. Portraying a teenage girl performing at a strip club – and thoroughly enjoying the experience – was definitely shocking. But the bigger shock was the genuine love that blossomed between Chuck and Blair.

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Jenny Loses Her Virginity to Chuck (Season 3, Episode 22, “Last Tango, Then Paris”)

There have been a lot of disturbing sex scenes on “Gossip Girl.” The Season 3 scenario that had Chuck deflowering Jenny Humphrey, who despite her attempts to be a bad girl, was younger and far less experienced then him was just plain gross. Chuck by this point was a high-school graduate, while Jenny was still a junior. Ed Westwick is in his twenties, while Taylor Momsen is the rare actual teenager who plays a teenager on television. Chuck only did it because he thought Blair no longer loved him. But it was definitely a low point for the character and the show.

Blair’s Princess Wedding Gone Wrong (Season 5, Episode 13, “G.G.”)

Everything about Blair’s romance with Belgian prince Louis Grimaldi was wrong. He was boring. Blair’s desire to be a princess, while in character, meant that she suppressed every part of her personality that made her fun to watch. No one wanted to see Queen B kowtowing to get the approval of real royal. So the implosion of her dream wedding was less of a shock and more of an answered prayer. The hundreds of guests at the wedding all got to see video of Blair telling Chuck that she still loved him thanks to Gossip Girl. The surprise was that the ceremony happened anyway – but that during the couple’s first dance, Louis coldly told Blair that their relationship was over and they had to pretend to be happy in public for the sake of appearances. Fortunately, Blair fled the reception with Dan’s help, rather than becoming a Princess Slave.

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Georgina Is Gossip Girl (Season 5, Episode 13, “G.G.”)

Since the first episode, the identity of Gossip Girl has been the show’s central mystery. In Season 5, viewers discovered that unrepentant troublemaker Georgina Sparks (Michelle Trachtenberg) was behind the all-knowing web site that chronicles everyone’s lives. It turned out that she was just filling in since the real Gossip Girl had gone AWOL, but it was one of the show’s most shocking reveals ever. Georgina later passed the torch to Serena. The finale may finally answer all of our questions about the mysterious “G.G.”

Chuck Wears a Onesie (Season 5, Episode 19, “It Girl Interrupted”)

“Gossip Girl” has influenced fashion. It made teens covet couture. It created trends, including headbands, and inspired a resurgence of the preppy look. Anna Sui was even inspired to create a real-life fashion line based on the show. Other real-life icons, including Vera Wang, guest starred. But no outfit on the show garnered more attention than the adult onesie that Chuck wore in Season 5. The normally dapper character donned a skin-tight red onesie known as a One Piece that is apparently a trend in Norway – and recently opened a boutique on tony Robertson Avenue in Los Angeles. He looked ridiculous and utterly unlike himself. There were about 100 blog posts condemning the abomination.