18 Side-By-Sides Of The "Gossip Girl" Cast On Their First Red Carpet Vs. Most Recent

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Hello, Upper East Siders! Gossip Girl here to, well, give you an update on the original Gossip Girl cast, now that the show is officially 16 years old. That's right, take it in — the show is now the same age that Blair and Serena were in Season 1. Let's take a look back at the cast on their earliest red carpets compared to their most recent, shall we? XOXO.

1.Leighton Meester (Blair Waldorf) on her first red carpet in 2003:

she's wearing cargo capris and a printed bomber jacket
Albert L. Ortega / WireImage

Leighton Meester on her most recent red carpet:

wearing a cream outfit with a dark purse

2.Blake Lively (Serena Van Der Woodsen) on her first red carpet in 2005:

closeup of her in a t-shirt
J. Merritt / FilmMagic

Blake Lively on her most recent red carpet:

she's wearing a gold jumpsuit

Since Gossip Girl, Blake has pivoted to movies, starring in films like The Age of Adaline, A Simple Favor, and The Rhythm Section. She will also be starring in the upcoming adaptation of Colleen Hoover's book, It Ends With Us.

Gilbert Flores / WWD via Getty Images

3.Penn Badgley (Dan Humphrey) on his first red carpet in 2003:

closeup of him in a short-sleeved button-down
Ron Galella / Ron Galella Collection via Getty Images

Penn Badgley on his most recent red carpet:

he's wearing baggy suit shorts with a matching trench coat, boots, and a skinny tie

Of course, Penn has had a thriving film and TV career since Gossip Girl. Most notably, he's starred as Joe Goldberg on You since 2018.

Marc Piasecki / WireImage

4.Chace Crawford (Nate Archibald) on his first red carpet in 2005:

closeup of him in a polo
Mark Sullivan / WireImage

Chace Crawford on his most recent red carpet:

closeup of him in a suit

Chace has also had several TV roles and most notably has starred as The Deep on The Boys since 2019 and recently guest starred on the show's spinoff, Gen V.

Gilbert Flores / Variety via Getty Images

5.Ed Westwick (Chuck Bass) on his earliest red carpet in 2005:

closeup of him in a polo
Evan Agostini / Getty Images

Ed Westwick on his most recent red carpet:

closeup of him in a suit

6.Taylor Momsen (Jenny Humphrey) on her first red carpet in 2000:

closeup of her as a kid wearing a long skirt and cardigan
New York Daily News Archive / NY Daily News via Getty Images

Taylor Momsen on her most recent red carpet:

closeup of her in dark eye makeup

7.Jessica Szohr (Vanessa Abrams) on her first red carpet in 2005:

closeup of her wearing a bandana on her head
Michael Tran / FilmMagic

Jessica Szohr on her most recent red carpet:

she's wearing a strapless dress with a long slit and her

8.Kelly Rutherford (Lily Van Der Woodsen) on her first red carpet in 1989:

her looking over her shoulder in a halter dress
Ron Galella / Ron Galella Collection via Getty Images

And just for fun, here she is with Paul Johansson aka Dan Scott from One Tree Hill at the same event:

the two hugging
Ron Galella / Ron Galella Collection via Getty Images

And here's Kelly Rutherford on her most recent red carpet:

she's got her hair tied back and she's wearing an empire style dress

Post-Gossip Girl, Kelly stuck around in the teen drama and CW world with roles in shows like Pretty Little Liars: The Perfectionists and Dynasty.

Stephane Cardinale - Corbis / Corbis via Getty Images

9.Matthew Settle (Rufus Humphrey) on his earliest red carpet in 1997:

closeup of him in a suit
Frank Trapper / Corbis via Getty Images

Matthew Settle on his most recent red carpet in 2015:

closeup of him in a suit underneath a large jacket

Matthew hasn't acted very much since his Gossip Girl days, but he did appear in an episode of Criminal Minds: Beyond Borders in 2016.

Ben Gabbe / FilmMagic

10.Zuzanna Szadkowski (Dorota Kishlovsky) on her earliest red carpet in 2009:

closeup of her in a dress at an event
Jerritt Clark / WireImage

Zuzanna Szadkowski on her most recent red carpet:

closeup of her in a lace dress

The actor who brought us the beloved Dorota has acted a bunch since Gossip Girl, including reprising her role on the show's 2021 reboot. She has also appeared on shows like Bull, Modern Love, and The Gilded Age.

Jamie Mccarthy / Getty Images

11.Connor Paolo on his earliest red carpet in 2007:

cloesup of him with long hair wearing a suit
Patrick Mcmullan / Patrick McMullan via Getty Images

Connor Paolo on his most recent red carpet:

closeup of him in a leather jacket with long curly hair

After Gossip Girl, Connor starred in the hit show Revenge. More recently, he's been on shows like Electric Dreams and The Resident.

Sean Mathis / Getty Images for SXSW

12.Margaret Colin (Eleanor Waldorf) on her earliest red carpet in 1987:

closeup of her wearing a blazer
Ron Galella / Ron Galella Collection via Getty Images

Margaret Colin on her most recent red carpet:

she's wearing polka dot pants and a bomber jacket

Margaret also reprised her Gossip Girl role in the reboot. She has also appeared on shows like Veep, Shades of Blue, and Chicago Med.

John Lamparski / Getty Images

13.Michelle Trachtenberg (Georgina Sparks) on her first red carpet in 1996:

young michelle in a long printed skirt with hair clips in her hair
Ron Galella / Ron Galella Collection via Getty Images

Michelle Trachtenberg on her most recent red carpet in 2020:

closeup of her in a long-sleeved sparkly dress

Michelle made a splash on the Gossip Girl reboot by reprising the role of Georgina. She also hosted the show Meet, Marry, Murder.

Michael Tran / AFP via Getty Images

14.Robert John Burke (Bart Bass) on his earliest red carpet in 1993:

closeup of him in a suit
Frank Trapper / Corbis via Getty Images

Robert John Burke on his most recent red carpet:

he's wearing a suit and has grey hair now

Robert has appeared in several movies since Gossip Girl, including BlacKkKlansman, Black Panther: Wakanda Forever, and Boston Strangler.

Noam Galai / Getty Images for 20th Century Studios

15.Sebastian Stan (Carter Baizen) on his first red carpet in 2006:

closeup of him in a suit with spiky hair
Patrick Mcmullan / Patrick McMullan via Getty Images

Sebastian Stan on his most recent red carpet:

him wearing all black with longer hair and a beard

Of course, Sebastian went on to land the massive role of Bucky Barnes in the Marvel Cinematic Universe. He also starred in Pam & Tommy, and the movies Fresh and I, Tonya.

Karwai Tang / WireImage

16.Wallace Shawn (Cyrus Rose) on his earliest red carpet in 1966:

closeup of him in a suit
Robert R. Mcelroy / Getty Images

Wallace Shawn on his most recent red carpet:

closeup of him with grey hair, wearing a button down shirt

Wallace appeared in the 2018 movie Marriage Story. He has also provided the voice of Rex in all of the Toy Story films and most recently also did voice work in The Addams Family 2. He also reprised his Gossip Girl role in the reboot.

Gary Gershoff / Getty Images

17.Kaylee DeFer (Ivy Dickens) on her first red carpet in 2005:

she's wearing low-rise jeans and holding up a betty crocker shirt
Rebecca Sapp / WireImage for General Mills

Kaylee DeFer on her most recent red carpet:

closeup of her in a suit

After playing Ivy in the latter seasons of the show, in 2013, Kaylee announced a break from acting to raise her son.

Jerod Harris / Getty Images

18.Kristen Bell (the voice of Gossip Girl) on her earliest red carpet in 2004:

she's wearing a mini dress and her hair is cut short
Kevin Winter / Getty Images

Kristen Bell on her most recent red carpet:

wearing a leather jumpsuit with shoulder length hair

Since Gossip Girl, Kristen has starred in House of Lies, The Good Place, Frozen, and more recently The Woman in the House Across the Street from the Girl in the Window. She also returned to narrate the Gossip Girl reboot.

Elyse Jankowski / Getty Images