XOXO, “Gossip Girl”: The Top 10 Episodes

gossip girl

Ladies and gentlemen, I will now risk any credibility I have left as a normal, heterosexual male, and present you with my final salute to my favorite guilty pleasure on television, Gossip Girl. Having just finished its run in fairly unceremonious fashion, I decided to take a look back at this once buzzed-about show and figure out what I loved (and hated) about it.

There was a time when Gossip Girl wasn’t just the best teen drama on TV, it was the only one that counted. Co-created by OC wunderkind Josh Schwartz, Gossip Girl felt like the even more elaborate, East Coast version of the aforementioned California-based show. Although its ratings were never great, it got into its groove midway through season one, and people started to pay attention. It was downloaded again and again on iTunes, it made critics’ top ten lists and it was even featured on a scandalous cover for Rolling Stone. Even though it hit at the beginning of the recession, this show about spoiled rich kids doing bad things actually prompted the CW to base their whole lineup around it.

But soon enough, as all things do, Gossip Girl faded from the American consciousness. The Vampire Diaries became the new CW show of note, following the “vampire everything” trend. The CW shuffled more teen dramas in and out of their lineup, some of which were minor successes, but most of which were not. And Gossip Girl hit a creative low peak. Where it was once campy fun, full of clever pop culture references and storylines both shocking and decadent, it became a convoluted mess, filled with an obnoxious amount of guest stars and dialogue so stiff you would think the original writers had died.

But as Monday night’s series finale proved, when Gossip Girl focused up, it was a great source of soapy escapism. So, with that said, here is my list of the ten best episodes of Gossip Girl. If you want to watch the finale, it is now available on Hulu Plus. Enjoy, and XOXO.

10) Season 6 – “New York, I Love You XOXO”: Once again, Monday night’s series finale really did have everything I love about this show. It was funny (Georgina describing Dan as the only one who would own a “hoodie,” for instance), sweet and completely over the top. Filled with not one, but two weddings, it gave everybody a happy ending and paired off all the couples in the most appropriate ways. Chuck and Blair. Dan and Serena. Nate and a good haircut. Hell, even the evil Georgina Sparks and Jack Bass found love together. As for the reveal of who Gossip Girl was (SPOILER ALERT! IF YOU HAVEN’T SEEN IT, BUT WANT TO, DO NOT READ ON), the revelation that it was actually Dan Humphrey, of all people, felt a bit strange at first, but made sense when you took the time to consider everything. Furthermore, it hardly mattered who it was after we got hilarious cameos from Kristen Bell and New York mayor Michael Bloomberg.

9) Season 3 – “The Last Days of Disco Stick”: Although the show had already started to feel a bit stale by the third season, this episode features the show’s best musical cameo in the form of Lady Gaga, and kicks off the Serena/Senator storyline, which was one of the most amusing past season two.

8 ) Season 2 – “Carnal Knowledge”: Another episode about a scandalous relationship, this one kicking off Dan’s tryst with his teacher.

7) Season 3 – “Last Tango, Then Paris”: What was perhaps the most devastating blow ever dealt to Gossip Girl fans occurred at the end of this episode, when Jenny loses her virginity to Chuck, just as Blair decides she’s ready to love him again. It made a lot of people mad, but it also made for great television.

6) Season 1 – “All About My Brother”: One thing to remember about Gossip Girl is that they were masters of the cliffhanger ending, and this one is particularly jarring. As Serena breaks down and begins to tell a secret to Blair, we expect just about anything to come out of her mouth, except for the words “I killed someone.”

5) Season 2 – “The Goodbye Gossip Girl”: This is, of course, where the show’s most beloved couple, Dan and Blair, get together. Unfortunately, it also ended up being the show’s early undoing. By playing out the romantic tension between the show’s two most interesting characters early on, the writers were forced to find ways to break them apart and get them back together again for the next four seasons.

4) Season 5 – “The Princess Dowry”: Of course, while most fans watched Gossip Girl from season three on to see where the Chuck/Blair romance would go, and once it became easy to figure out that they would end up together in the end, it was a lot more entertaining to see who they’d date in the interim. It was probably the most polarizing plotline of the show, but the will they/won’t they of the “Dair” (Dan and Blair) relationship ultimately became my favorite element about the later seasons of Gossip Girl.

Dan and Blair were so great together for the opposite reason Dan and Chuck were so great together. While the latter couple was so alike, the former was so different. Dan and Blair’s bickering flirtation was always among some of the best writing the show ever produced. Sadly, while most of the characters on Gossip Girl hopped in and out of bed with each other without so much as a second glance, it took about a season and a half to finally get Dan and Blair together. It ultimately happened here, in season five’s “The Princess Dowry.” Of course their doomed love story didn’t last long. But in this brief moment, when after months of waiting it actually happened, the result was pretty damn satisfying.

3) Season 1 – “Victor/Victoria”: “The Goodbye Gossip Girl” was the first time fans got to see Dan and Blair together as a couple, but “Victor/Victoria” is their first romantic encounter, and OMG was it steamy. Blair does a mini-striptease at Chuck’s club, and then loses her virginity to him (Chuck Bass is really good at helping girls do this) in the back of his limo. It was the episode that forever cemented what would ultimately be the main source of drama on the show.

2) Season 1 – “Pilot”: The reason the Gossip Girl pilot is so successful is that it sets up every major dynamic the show would ultimately explore. Some of it is subtle (or at least, subtle for Gossip Girl), but it’s all there in the opening episode. I can’t believe I’m saying this, but in setting up the rules of the show, it’s probably one of the better pilots I’ve ever seen.

1) Season 2 – “O Brother, Where Bart Thou?”: While Serena was always meant to be the lead of the show, Blair has been the more compelling character from the beginning. Here, we see a softer side to her, and to Chuck, as she helps him grieve the loss of his dead father. It might have the show’s least clever title, but “O Brother, Where Bart Thou?” is Gossip Girl’s emotional high point. It’s even, dare I say it, moving. And the decision to kill off Chuck’s father was just ridiculous enough to work. The decision to bring him back, however, not so much. But that’s what’s great about this mid-season finale. It was a wonderfully sappy and over-dramatic episode that Gossip Girl never quite matched after it aired, no matter how hard it tried. Still, I can re-watch it now and be reminded of just why my unlikely love for this show began in the first place.

  • Pingback: See you later, dummies: The 10 best episodes of “30 Rock” | Heave Media()

  • poopydoop

    I think there is a typo… unless on #4 dan and chuck became a couple and i totally missed that…

  • lkj

    you kept saying dan instead of chuck

  • Annoeska

    My favourite is S04E22 for sure!

  • Maria

    You made loads of mistakes

  • ff

    U messed everything up! U kept saying Dan and Blair for chuck and Blair -_- and where the hell did chuck and Dan come from?????? Read ur articles before u post them online !

  • Some kid who loves Chuck&Blair

    umm it’s Chuck not Dan, and also, #3 is actually titled, “Victor/Victrola”