The dynamic characters of the iconic TV series, Gossip Girl, will never be forgotten by the kids of my generation. From beautiful Serena to devilish Georgina, pretty much anyone can find a character that he or she relates to the most. Some of them we love to hate while others we hate to love. Today, I’m going to profile some of my favorite (and least favorite) Upper East Siders.
First, of course, is Serena van der Woodsen. Portrayed by Blake Lively, Serena is a party-girl turned good after dating the infamous Dan Humphrey. Beautiful blonde locks and an enchanting smile pretty much earn Serena anything she wants including the hottest men of the Upper East Side. Her best friend is Blair Waldorf, and though it seems that they are constantly fighting about something, the friendship is forever. Sometimes it’s hard to love S, but personally, she’s one of my favorite characters. Maybe it’s just because I’m obsessed with Derena. Oops.
The queen bee of the Upper East Side is Blair Waldorf, played by Leighton Meester. I’ve always struggled with how exactly to feel about B. Like most rich girls, she’s bratty, entitled, and extremely overdramatic, but something about her is definitely endearing. Plus, her relationship with Chuck Bass may be the most iconic fictional relationship of our time. Though Serena is usually the most known for having many, many boyfriends, Blair’s number is up there too especially if a husband counts as two. The queen bee temporarily upgraded to real life princess, but as usual in Gossip Girl, it didn't really turn out how she wanted it to.
Next, Nate Archibald fits the hot, rich guy mold perfectly. Chace Crawford used his smoking looks for good when he took on the role of one of the Upper East Side’s finest. Nate, like most characters on the show, has dated most of his girl-friends, but he has always struggled with who he is without the girls, money, or Vanderbilt family name. After his father was thrown in jail for embezzlement, he works even harder to find himself and lands the position of editor-in-chief of The Spectator. He’s best friends with the Chuck Bass and Dan Humphrey.
Now, for my favorite character: Dan Humphrey, played by Penn Badgley. I know, I know that it’s a strange choice, but since his first appearance, I’ve fallen in love with a fictional character. Raised in Brooklyn, Dan has always felt like an outsider. In high school, he was basically ignored by the social hierarchy until he started dating Serena, and this experience later serves as fuel for his book entitled Inside. My favorite episodes of the series are the ones in which he and Serena are a couple. My least favorite are the ones that show him and Blair together. Literal yuck. I can’t say that I’m in love with Dan’s homely father, Rufus, or his God-awful sister, Jenny, and I’ll hit on Jenny a little later.
Chuck Bass, portrayed by Ed Westwick, is the character I would say that I love to hate. Before Blair Waldorf, he was a disgusting, womanizing child, but after the love of his life, he made a beautiful transformation. I like to think of Chuck as a sort of rich, alcohol-loving butterfly if that makes sense. Poor Chuck had a bit of a difficult childhood complete with a rough-around-the-edges father, a “dead” mother, and way too much money. In my opinion, Blair mended who was simply a scorned child and slowly but surely turned him into a man who anyone would be proud to be with.
Taylor Momsen created a character in Jenny Humphrey that literally sends chills down my spine. Little J is the definition of a rebellious child since she runs away multiple times, doesn’t understand what grounded means, and knows no loyalty. Looking back, Jenny is extremely talented as a seamstress, but her attitude leaves me with absolutely no affection for her. Plus, she ruined Chuck and Blair, so I’m bound to hate her. In fact, I’m fairly certain that she’s my absolute least favorite character in the show. There are a few others that make my skin crawl as well like Ivy Dickens, Juliet Sharp, and Vanessa Abrams, but Jenny Humphrey takes the cake. What did Nate ever see in her anyway?
I’m going to finish the post out with my second favorite character, and beware, it’s another weird choice. Dorota Kishlovsky is Blair Waldorf’s loyal housekeeper, who basically raised the queen bee. Again, I know what you’re thinking. I should like Serena or Blair or even Eric van der Woodsen, but Dorota, played by Zuzanna Szadkowski, has some of the most inspirational lines in the six season series and stole my heart. She is kind of like the mother of the show, and honestly, she’s a better mother to B and S than Eleanor Waldorf and Lily van der Woodsen.
We all have our opinions on the most famous Upper East Siders of the 20th Century, and don’t forget to tell me what yours are. Happy kommenting :)
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