Gossip Girl: 8 Stars Who Became A-Listers (And 7 Who Flopped)

Good morning Upper East-Siders, more than ten years ago the first episode of the teen sensation we would come to know as Gossip Girl aired across millions of television screens in the US. Merely a year later, audiences across the world were enthralled with the scandalous lives of Manhattan’s elite, as ridiculous and farfetched as they may seem. Gossip Girl was everywhere for a solid six years: in magazines, on social media, and most importantly on television. Absolutely everyone between the ages of 14 to 25 was obsessed with learning whether these privileged people would finally find their happy endings.

It has now been six years since the show ended, and it has gotten rather quiet around the actors behind the phenomenon. Die-hard fans will have followed their favorites through independent films, off-broadway plays, and failed television projects, but only a few of the original cast members has remained relevant.

Let’s have a look at those actors, who either have managed some of this century’s top roles or have a most promising year ahead, and those who unfortunately, seem to have gotten lost in the wonderland that is Hollywood.

Without further ado we present: Gossip Girl: 8 Stars Who Became A-Listers (And 7 Who Flopped).

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15 A-Lister: Blake Lively

Blake Lively has kept busy these past few years. On Gossip Girl she played Serena, a flaky but charismatic young woman who, despite her best efforts, does not quite find her way in the end. In real life, Lively has done well for herself. The actress has starred in a variety of multi-million dollar productions, and has several more blockbusters lined up.

In 2015 and 2016, she played the female lead in The Age of Adaline and The Shallows, respectively. Both were not exactly box-office hits, but were well received by critics. Her upcoming projects include the thriller A Simple Favor (due to be released in September 2018), and The Rhythm Section, which is currently on hiatus as Lively recovers from an on-set injury.

14 Flopped: Ed Westwick

Ed Westwick Gossip Girl

Ed Westwick may have been able to charm young girls on screen as the devilish Chuck Bass, but off-screen he seems to be the kind of person one should stay as far away from as possible. Late last year, three women came forward with charges towards Westwick, which he vehemently denied, but those charges are now under review by the Los Angeles District Attorney’s office.

In addition to these allegations, Westwick’s more recent projects have all gone downhill.

His first lead role after Gossip Girl, as Kent Galloway in Wicked City lasted all of eight episodes, before it was cancelled. After the accusations, BBC pulled his series White Gold, and recast his character in the Agatha Christie adaptation Ordeal by Innocence.

13 A-Lister: Sebastian Stan

You know and love him as Bucky Barnes, but before Sebastian Stan took over the Marvel universe as the most lovable antagonist, he terrorized Manhattan’s darlings. As Carter Baizen, he charmed both Serena and Blair, but also got Chuck and Nate in trouble with his substance abuse and gambling problems.

In the past few years, Sebastian Stan has become the face of beloved Marvel character Winter Soldier, and has portrayed him in no less than five separate movies, including Avengers: Infinity War. He also booked a few of guest stints on television hits such as Once Upon a Time, and has played one of America’s most hated men, Jeff Gillooly in I,Tonya. The world expects great things from Mr. Stan in the future.

12 Flopped: Michelle Trachtenberg

What ever happened to Michelle Trachtenberg? The young actress was celebrated for her breakthrough performance as Dawn in Buffy the Vampire Slayer, being the title character’s little sister. Before joining Gossip Girl, she guest starred on several programs including House, Six Feet Under, and Law and Order: Criminal Intent.

As Georgina Sparks, Trachtenberg became one of the series’ favorite villains.

Whether she went up against Serena, tricked Dan into taking care of her child, or eventually took on the identity of Gossip Girl, she was pure entertainment. However, Trachtenberg has not been able to recreate her Gossip Girl success. She guest starred in a few more programs, amongst them Sleepy Hollow, and NCIS: Los Angeles, but the big break never came.

11 A-Lister: Armie Hammer

On a scale of one to ten, how well do you remember Armie Hammer’s role on Gossip Girl? He does indeed belong to the category of long forgotten guest stars. He briefly appeared in season two as Gabriel Edwards. Gabriel started dating Serena, while secretly seeing her friend Poppy, and eventually conned Serena into providing him with funds.

Since then, Hammer has moved on to much bigger things than playing a preppy con man. He played the twin-set Tyler and Cameron Winklevoss on The Social Network, and of course, made audiences swoon as Oliver in Call Me By Your Name. From Gossip Girl to starring in an Oscar-nominated drama - Mr. Hammer has definitely carved out a name for himself. 

10 Flopped: Leighton Meester

If there is one person we would have liked to come out of Gossip Girl a star, it would have been Leighton Meester. She dazzled with her performance as the vulnerable but tough leading lady Blair Waldorf.

Unfortunately, Meester has not made it back into the limelight just yet.

While she did star in a handful of wonderful independent movies such as the LGBT comedy Life Partners, and the heart-felt drama Like Sunday, Like Rain, she has yet to find her way back to the mainstream masses. She did try to do so with the FOX comedy Making History, which sadly, did not make history and was cancelled after one season.

She was most recently cast as the female lead in the upcoming ABC pilot Single Parents, so let’s pray this will solidify her return to prime time television.

9 A-Lister: Willa Holland

Willa Holland may have come to fame thanks to her role as Kaitlin Cooper on The OC, but one should not forget she also spent some time on Gossip Girl. Holland joins the cast in season two and three in the role of Agnes Andrews, a model-turned-troublemaker that challenges Jenny Humphrey’s career, as well as the relationship with her family.

Since then, Holland may not have dabbled in too many projects, but the one that she has had a continuous presence in, is massive. Just as Gossip Girl ended, Arrow began - and so the world was introduced to Thea Queen, Oliver’s sister. While the character does not exist in the Green Arrow comic book series, Holland has made Thea her own - she has become an integral part of the series.

8 Flopped: Taylor Momsen

Oh, little J. Taylor Momsen has started her career in the spotlight at the tender age of 2, when she started modeling, and stole hearts as Cindy Lou Who in How the Grinch Stole Christmas! long before she finished elementary school. She then joined Gossip Girl as a young, innocent teenager to take on the role of a young, innocent teenager: Jenny Humphrey.

However, as Momsen grew into an adult seemingly overnight, so did Jenny.

Starting in season three, Momsen sported dark eyeliner, long platinum blonde curls, and the highest of heels. At the end of the series’ fourth season, Momsen decided not to return, and to focus on her music career. She has not been seen on television since.

7 A-Lister: Hilary Duff

Admittedly, Hilary Duff was a star long before she joined Gossip Girl. She defined the childhood of many as Disney’s Lizzie McGuire, and appeared in classic early 2000s romantic comedies such as A Cinderella Story. Not to mention she has an incredibly successful music career. Hilary appeared in the third season of Gossip Girl as Olivia Burke, and took part in one of the series’ most scandalous scenes.

After Gossip Girl, she continued her work on television with guest appearances on Community, Raising Hope, and Two and a Half Men, before she finally settled into a lead role as Kelsey Peters in Younger. Now in its fifth season, alongside the charming Sutton Foster, it's easy to see Hilary Duff is doing just fine.

6 Flopped: Matthew Settle

Before joining the main cast of Gossip Girl, Matthew Settle guest starred on a variety of television shows including ER, CSI: Miami, and Brothers and Sisters, as well as portraying Ronald C. Speirs on the 2001 mini-series Band of Brothers. He joined Gossip Girl in 2007, where he played Dan and Jenny's kind-hearted father.

As Rufus Humphrey, Settle did a lot more than support his children. He had his own career as a musician, and most importantly, his romantic relationship with Lily van der Woodsen to deal with. After the series ended, Settle has taken a step back from the television world, or so it seems. He starred in a handful of mildly successful movies, including the horror flick Ouija, but none of his projects comes even close to the success of Gossip Girl.

5 A-Lister: Elizabeth Hurley

She is most well-known for her role as Vanessa Kensington in the Austin Powers films, and for playing the Devil opposite Brendan Fraser in Bedazzled.

Elizabeth Hurley could be considered an important part of British film culture.

On Gossip Girl, Hurley took on the role of the powerful business woman Diana Payne in season five. Diana not only finds herself a boy toy in Nate, but also ends up revealing that she is Chuck’s real mother, who he originally believed had passed away during childbirth. Only a few years after her stint on Gossip Girl, she bagged the lead role in the E! drama The Royals. The Royals may not be quality TV, but it certainly offers Hurley constant exposure.

4 Flopped: Kaylee DeFer

Prior to Gossip Girl, Kaylee DeFer appeared on a wide range of television series such as Nickelodeon favorite Drake and Josh, the comedy The War at Home, and crime dramas CSI: Miami, Bones, and Ghost Whisperer.

However, many of these roles were mere guest appearances, so when she joined Gossip Girl in 2011 as Charlie Rhodes/Ivy Dickens, DeFer bagged her first major television role.

In season four, Ivy tried to infiltrate the van der Woodsen family by pretending to be Serena’s long lost cousin. She was hired by Carol Rhodes, Lily’s sister, to gain access to the the family trust fund. However, after Gossip Girl ended, DeFer has disappeared from the small screen never to return again... for now.

3 A-Lister: Katie Cassidy

Remember one of the most manipulative women on the Upper East Side? In season four, Katie Cassidy's Juliet Sharp made it her mission to get revenge on Serena, who she blames for her brother’s incarceration. She also wooed Nate for a while, but that was never meant to last.

Even before joining Gossip Girl, Cassidy had made a name for herself with recurring roles on shows such as Supernatural and 7th Heaven, as well as lead roles in Harper’s Island and Melrose Place.

A-Lister might be a bit much, but Katie Cassidy continues to land respectable television roles even after Gossip Girl.

She is currently best known for portraying Laurel Lance, and later on Black Siren in the CW’s Arrow.

2 Flopped: Chace Crawford

Let’s talk about Chace Crawford. The young actor was mostly unknown before he took on the role of Nate Archibald on Gossip Girl. While he had lended his voice to a few characters on Family Guy, and appeared in a few smaller films, it was Gossip Girl that catapulted the young man to fame.

Nate Archibald was everything one would expect from a preppy Upper East Sider: handsome, rich, and incredibly charming. Often times he was also clueless, and especially in later seasons, and failed to make any of the revolving storylines his own.

After the end of the series, Crawford took on the lead role of Billy LeFever in the ABC drama Blood & Oil, which unfortunately did not stand the test of time and was not only cancelled after one season, but even saw its 2015 season shortened.

1 A-Lister: Penn Badgley

On Gossip Girl, Penn Badgley portrayed Dan Humphrey, the boy from the wrong side of the tracks who fell in love with not just one, but two Upper East Side queens. He was also revealed to be the mastermind behind the notorious gossip website, which made no sense, but was widely accepted nonetheless.

Since then, Badgley has starred in a variety of critically successful independent films such as the musical drama Greetings from Tim Buckley, or the Shakespearean action thriller Cymbeline. However, it is his upcoming project that could cement his A-Lister status and bring him back to television screens for good. Badgley was cast in the lead role in an adaptation of Caroline Kepnes’ novel You for Lifetime. The psychological thriller is a Greg Berlanti project, so there are good chances it will become a success.


Which other Gossip Girl stars can you think of that gained A-Lister status or flopped? Share them in the comments!

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