It's hard to believe it's been nearly 10 years since the CW brought us new episodes of Gossip Girl, the series about a group of New York City teens attending a tony private school while getting into all sorts of trouble that they couldn't hide from the anonymous blogger constantly threatening them, no matter how hard they tried. There was nothing like getting lost in the totally enviable but unrelatable lives of Serena van der Woodsen and Blair Waldorf after a long day.
Now that Gossip Girl is getting the reboot treatment (the new show premieres on July 8), we can't help but wonder about the cast of the original hit show.
It's been a long time since their days playing the young aristocrats of the Upper East Side's best families, and their lives, careers, and appearances have undoubtedly changed quite a bit. So before we tune into the HBO Max reboot, we decided to take a look back at our favorite Gossip Girl characters and see what the actors who played them are up to now.
Some of the show's cast members have gone on to even bigger stardom, while others kind of disappeared off of our radars since the original Gossip Girl came to an end. But we've managed to track them all down, so come and take a little walk down memory lane with us and find out what the OG cast is up to now.
Then: Blake Lively
No matter how much we adored her wardrobe as Serena van der Woodsen, none of us really wanted to be like actress Blake Lively as the lead character in Gossip Girl — at least not in the beginning. She did eventually win most of us over, though. Blake earned herself a lot of fans during the show's six seasons.
Now: Blake Lively
The same year the show ended, Blake married fellow A-list actor Ryan Reynolds. They've since had three children, and Blake has gone on to star in several movies including the Age of Adaline and the Shallows. She's also quite well known for goofing around with her notoriously humorous hubby on social media.
Then: Leighton Meester
If Serena was the one we didn't want to love but did anyway, actress Leighton Meester's character, Blair Waldorf, was actually the one we loved to hate. She was just so good at being a mean girl that we were all convinced for at least a while that Leighton herself was just as bitchy as Blair.
Now: Leighton Meester
Over the years, Leighton has shed her glamorous "Blair" mask and revealed more of her true self on social media. Since the show ended, she's worked on Broadway a bit, appeared in a handful of films and shows, married OC actor Adam Brody, and become a mom. She's also expected to star in the upcoming Netflix original film, The Weekend Away.
Then: Penn Badgley
Actor Penn Badgley's character, Dan Humphrey, was the outsider of the Gossip Girl group (he lived in Brooklyn, after all), and while we started out adoring him, by the end of the series, his conniving side came out. It actually took us a while to put two and two together, but he went on to star in another hit show.
Now: Penn Badgley
Years after the end of Gossip Girl, Penn resurfaced in a starring role as a totally adorable (but also seriously creepy) psychopath in the hit Netflix original series You, which is based on the novel of the same name by author Caroline Kepnes. He also got married (to Domino Kirke in 2017) and became a dad for the first time in 2020.
Then: Chace Crawford
Actor Chace Crawford played the super cute, albeit seemingly shallow Nate Archibald on Gossip Girl and was the object of many a teenage crush. Nate genuinely tried to be a nice guy, which made us all love him even more. And, you know, those eyes and that hair. It was hard not to fall for him.
Now: Chace Crawford
Chace is still playing eye candy, these days as minor superhero "the Deep" on the Amazon Original series The Boys. The Texan actor, who now calls former Dallas Cowboys star Tony Romo brother-in-law, has also acted in several films and TV series since his Gossip Girl role came to an end, including Blood & Oil and Eloise.
Then: Ed Westwick
British actor Ed Westwick was perfection as Gossip Girl's Chuck Bass. The character was utterly loathsome — until he wasn't — and when it was time for us to sympathize with him and see him as the feeling, breathing, completely traumatized human that he was, Ed sold us that story, too.
Now: Ed Westwick
Ed's been pretty busy since Gossip Girl ended, acting in several TV series and a few films throughout the years. He also landed in some hot water in 2017 and 2018 when he was accused of raping two women and sexually assaulting another. However, charges were not brought against him due to insufficient evidence. He's currently working on the film Wolves of War.
Then: Taylor Momsen
Jenny Humphrey, played by actress Taylor Momsen, was arguably one of the most hated characters on Gossip Girl. She was super annoying and proved to be among the most disloyal of the bunch. Although Jenny started out sweet, many fans of the show were shocked to see how she evolved over the course of the series.
Now: Taylor Momsen
Taylor pretty much stopped acting after Gossip Girl, instead focusing on her career as a musician. She's the lead singer of the rock band The Pretty Reckless. The band's fourth studio album, Death by Rock and Roll, was released in February 2021, and Taylor has been busy promoting it on social media.
Then: Connor Paolo
Serena's brother, Eric van der Woodsen, was a beloved character on Gossip Girl for many reasons. He was sweet and kind and one of the few openly gay characters on primetime TV at the time. We loved him and still do, largely in part due to actor Connor Paolo's on-point portrayal.
Now: Connor Paolo
When his time on Gossip Girl ended, Connor immediately picked up a recurring role on the popular ABC series Revenge, and since then he's done episodic work on a number of shows and is set to appear in several upcoming films. He also ventures into music a bit and shares some of that on social media.
Then: Michelle Trachtenberg
Those of us who were fans of actress Michelle Trachtenberg as Harriet the Spy when we were kids were thrown for a loop when she played the catty and conniving Georgina Sparks on Gossip Girl. She wasn't a series regular, but whenever she popped up on the show, fans knew the drama was about to ramp up.
Now: Michelle Trachtenberg
Michelle has always been a busy actress, and that didn't change after Gossip Girl. She has continued to do episodic work on various TV shows, and held recurring roles on series including Guidance, Robot Chicken, and Human Kind Of, though she hasn't been in anything since 2018.
Then: Kelly Rutherford
It was always hard to understand Lily van der Woodsen as a mother, and actress Kelly Rutherford was so good at portraying the WASP-y aristocrat. She totally had us convinced that she was the cold, uncaring character she portrayed. Kelly has serious acting chops that have served her well.
Now: Kelly Rutherford
Kelly has had a thriving career on television since the end of Gossip Girl. She did episodic work for a while, then landed recurring roles on several series including Pretty Little Liars: The Perfectionists and the Dynasty reboot. She's also appeared in some TV movies and mini-series.
Then: Matthew Settle
Matthew Settle's Gossip Girl character, Rufus Humphrey, was the musician single dad of Dan and Jenny, and while he made some questionable parenting choices (like many of the parents on the show), he was a character fans truly felt for. He was the underdog, and people rooted for him throughout the series.
Now: Matthew Settle
Matthew Settle has kept a fairly low profile since Gossip Girl ended, though he has appeared in a few TV movies and a couple of smaller films including 2017's Valentine. He's quiet on social media as well. He no longer posts on his Instagram account and his Twitter hasn't tweeted since 2016.
