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Gossip Girl: Guest Stars, Ranked

Gossip Girl is a teen drama television series based on a book series of the same name. It ran for six seasons, from September 19, 2007, to December 17, 2012, and it was about an affluent and attractive group that lived on the Upper East Side in New York. There was the it girl Serena van der Woodsen, the Queen B Blair Waldorf, the lonely boy Dan Humphrey, the jock Nate Archibald and, of course, Chuck Bass.

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But this thrilling series also featured many exciting guest stars! Some were just around for a bit, playing themselves at star-studded events in Manhattan, while others stuck around for several episodes, playing made-up characters. And the best ones are ranked below...

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13 Ivanka

For those who don’t know, Ivanka’s parents are the present of the United States and his wife, and this well-known woman played herself on one episode in 2010 - “Easy J”; her husband (Jared Kushner, who currently serves as the president's senior advisor) portrayed himself alongside her, too! Besides popping up on this hit TV series, she is also a businesswoman, a fashion designer, an author, a reality television personality and a politician. Her other television appearances include being a guest judge on Project Runway's third season and Project Runway: All Stars’ fourth season, as well as being on The Apprentice and Celebrity Apprentice.

12 Florence Welch

Florence Welch is the vocalist and songwriter of the indie rock band Florence and the Machine. This group’s debut album was released in 2009, but Florence Welch has been up to more than just this; besides being a musician, singer and songwriter, she is also a producer. Furthermore, in 2018, she released a book called Useless Magic, which is a collection of lyrics and poems. And, of course, she played herself on this television show, as her band appeared in one episode in 2011 - “Panic Roommate”; amidst all the craziness that was happening (like in every episode!), Florence and the Machine was playing at a party.

11 No Doubt

Another musical guest that showed up on Gossip Girl was No Doubt. This rock band formed in 1986, and the lead vocalist is Gwen Stefani. But within this fictional world, they were a group called Snowed Out. The episode was an iconic one from 2009, which was titled "Valley Girls", and in it, they performed a cover version of the Adam and the Ants song "Stand and Deliver". This particular episode will be touched upon more later, but for now, just think back to Gwen Stefani on this show, which was a fun surprise that many may have forgotten about!

10 Lex Meester

One of the main stars from this hit show is Leighton Meester, who played Blair Waldorf. As most fans know, this actress is married to a fellow star in real life: actor Adam Brody, who was on another teen drama; he played Seth Cohen on The O.C.! But how many people know about Leighton Meester’s brother? His name is Lex Meester, and in 2009, he played an NYU Student on an episode that was called “The Freshmen”. According to IMDb, he was diagnosed with brain cancer in infancy. After horrible headaches and surgeries, he was declared fully disabled in 2011. Since then, he's had eight more surgeries.

9 Cecily von Ziegesar

This book series was written by Cecily von Ziegesar, and she, too, has shown up on Gossip Girl! Yes, she played herself in an episode from 2011, which was called “The Wrong Goodbye”. And here is a fun fact for everyone: When Cecily von Ziegesar was a teenager, she commuted to Manhattan at 6:00 a.m. every day to attend The Nightingale-Bamford School, according to Wikipedia, which sounds a lot like the this TV show!

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Her other book series include The It Girl and Gossip Girl: The Carlyles, but she will always be known for this original series.

8 Tinsley Mortimer

Tinsley Mortimer played herself on two episodes from 2008 - “The Serena Also Rises” and “Summer Kind of Wonderful”. Since Tinsley Mortimer is a socialite in real life, it made sense to have her appear at some of the glam events and parties seen on this television show.

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Plus, since then, she has gone on to appear on TV regularly, since she is a cast member of Bravo’s The Real Housewives Of New York! Both of these shows are known for their drama, and it is neat for RHONY fans to go back and see her in this setting.

7 Project Runway Judges/Mentors

Reality TV and Gossip Girl collided far more than just once, and many of the stars from Project Runway and Project Runway: All Stars appeared on this teen series. For instance, we saw designer Isaac Mizrahi and Georgina Chapman, who are judges on Project Runway: All Stars and designer Michael Kors, who used to be a judge on Project Runway. Karlie Kloss was on an episode in 2010, and she has stepped into Heidi Klum’s shoes on Project Runway’s 17th season, as the host and executive producer. And, of course, Jenny Humphrey met with Tim Gunn, who served as the mentor on Project Runway until this year.

6 Cyndi Lauper

Since Blair was a fan of Cyndi Lauper’s, this singing sensation showed up at her birthday once! Yes, in 2008, on an episode called “Bonfire of the Vanity”, Cyndi Lauper portrayed herself. With songs like "Girls Just Want to Have Fun", "Time After Time" and "All Through the Night” and with a career that spans over 40 years, this was definitely an iconic moment on Gossip Girl, and she is definitely one of the biggest guest stars on this list! Plus, if we did not already sort of want to be Blair, this surely made us envy her life a bit more.

5 Krysten Ritter & Brittany Snow

One of the coolest episodes of this show is called “Valley Girls” - the one we said we would mention again! See, it told the backstory of Lily and Carol Rhodes. Lily is, of course, Serena van der Woodsen’s mother, and she was played by actress Brittany Snow, who is known for the Pitch Perfect movies. And her sister, Carol, was played by actress Krysten Ritter, who also played Jane Margolis (Jesse’s girlfriend) on Breaking Bad. Seeing these two in the ‘80s - with their fun fashion, crazy love stories and night that resulted in Lily behind bars - gave some interesting perspective.

4 Lisa Loeb

Lisa Loeb - who is a singer-songwriter, producer, touring artist and an actress and author - is best known for the hit song, "Stay (I Missed You)". But she has also starred in Dweezil & Lisa, a weekly culinary adventure for the Food Network, and has appeared in films such as House on Haunted Hill, Fright Night, Hot Tub Time Machine 2 and Helicopter Mom. Oh, and she portrayed herself in Gossip Girl! Fans met her through Rufus Humphrey’s musical career, and the two were even cozied up together in the series finale, causing us to believe that they were an item.

3 Rachel Bilson

Speaking of the series finale… We could go on and on when talking about that episode, but instead, we will just focus on another guest star seen there: Rachel Bilson, who appeared as herself in this one episode from 2012! This actress is known for roles in things like the movie Jumper and the television series Hart of Dixie, but she is best known as Summer Roberts from The O.C. (which is interesting, since, as mentioned, Leighton Meester married Rachel Bilson’s co-star, Adam Brody, in real life!). Yes, seeing her was just another cherry on top.

2 Hilary Duff

A guest star that really hung around was Hilary Duff, who was Olivia Burke in this series. This character, who was around for six episodes, was actually a famous actress, but clueless Dan Humphrey didn't even know who she was. This made Olivia like him even more, and it led to that interesting scene between these two and Vanessa.

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In real life, Hilary Duff starred on Disney Channel’s Lizzie McGuire and went on to have a singing career and two adorable children. But before becoming a mom, she was just another NYU student on Gossip Girl!

1 Kristen Bell

Of course, this list is wrapping up with Ms. Kristen Bell, who was the voice of Gossip Girl. This actress has starred in movies like Couples Retreat, When in Rome, Bad Moms and Frozen, as well as in the NBC comedy series The Good Place. But for fans of this teen drama, her voice is synonymous with the dramatic stories and exciting plots surrounding Serena, Blair and their friends. So when Kristen Bell’s face was finally shown at the end of this series, it was a bittersweet moment - one that has gone down in history.

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