10 Must-Watch Movies Starring The Cast Members Of Gossip Girl

Between 2007 and 2012, a popular novel-turned-television-show was born. Everybody likes a little drama and gossip, especially if it’s on the television screen. When Gossip Girl premiered on September 19th, 2007, fans of the novel were ready, while other fans gathered to watch privileged teenagers attend Upper East Side schools, while dealing with heartache, scandals, and a text-message thread with everyone’s deepest, darkest secrets. The characters in Gossip Girl, as fans know, are subject to questionable life choices, which may or may not be the intrigue of the show.

Some of the cast reached stardom very fast, while others have been in show business for years; either way, the actors and actresses that make up the ultra-successful series have had some impressive roles in movies, whether they were before or after Gossip Girl.

10 Blake Lively – A Simple Favor (2018)

Fashionista, advocate, and better half to actor Ryan Reynolds, Blake Lively had made quite the name for herself. Prior to Gossip Girl, she had starred in movies such as The Sisterhood of the Traveling Pants and Accepted, but one of the best movies she’s starred in thus far is A Simple Favor. Blake plays Emily Nelson, who is, like Serena van der Woodsen, upper-class.

Also starring Anna Kendrick, who plays Stephanie Smothers, finds out Emily has gone missing and takes it upon herself to find out what happened. Emily’s character is dark, mysterious, and has way more secrets than Stephanie might not want to find out. Blake Lively plays a fabulous, and put together character, much like her role in Gossip Girl.

9 Leighton Meester – Like Sunday, Like Rain (2014)

If anyone has seen at least one episode of Gossip Girl, they’ll know that Blair Waldorf, who is played by Leighton Meester, isn’t meek or attracted to niceties. She’s the best friend of Serena can der Woodsen, which might be one of the most toxic relationships on the show. She’s the ultimate “Queen Bee” of Constance Billard School of Girls, and isn’t to be messed with; so it’s refreshing to see Leighton playing a role that’s quite opposite of Blair. Leighton stars as Eleanor in the movie called Like Sunday, Like Rain.

After a blow-up at her current job involving her chaotic boyfriend, she finds herself out of a job and needing a new place to live. She takes a job as a nanny to a young cello player named Reggie, played by Julian Shatkin, who seemingly has it all, but doesn’t have a lot of family or friends to be there for him. Together Elanor and Reggie form a unique bond that came around at the right time. Leighton takes on her character in stride while showing a softer, emotional side.

8 Penn Badgley – Margin Call (2011)

So far, Penn Badgley has made quite the name for himself in popular television shows, but he’s also played some pivotal characters in the movie industry as well. J.C. Chandor’s Margin Call was just what Penn needed to further prove he can slip into a more mature role after Gossip Girl. Penn plays a character named Seth Bregman in Margin Call, a movie based on the early stages of the real 2008 financial crisis.

The story takes place at a Wall Street investment bank, which focuses on a group of investment bankers fighting the clock to save the company, in light of a major financial decline. Margin Call focuses on the corruption, capitalism, greed, and financial fraud that took place around this time. The movie headlines a lot of other well-versed actors such as Kevin Spacey, Zachary Quinto, Simon Baker, Demi Moore, and Stanley Tucci.

7 Chace Crawford – Undrafted (2016)

Chace Crawford’s Nate Archibald was quite the heartthrob “nice guy” of the Gossip Girl bunch, and made fans swoons worldwide; since then, Chace has acted in several other movies, Undrafted included. Chace plays the role of Barone, just one of several underachievers that are looking to play a bit of leisure baseball for the summer.

The bunch each have their own quirks, and as innocent as the game started out, they realize it’s much more than that when the competition gets heated, and the team comes together for a bigger purpose. Undrafted is a comedy that isn’t to be taken seriously but is a good watch nonetheless.

6 Ed Westwick – Chalet Girl (2011)

Chuck Bass, played by Ed Westwick, also known as the male Blair Waldorf, is handsome, but also has some major issues. At the end of the Gossip Girl series, Chuck made the right changes, but along the way, his time on Gossip Girl included scandal after scandal; fortunately, even before the show wrapped up, Ed was able to continue to find work.

For example, he starred in a rom-com movie called Chalet Girl, which also stars Felicity Jones as Kim Matthews, once a champion skateboarder. Ed plays Jonny, Kim’s boss, as she takes a catering job in a posh chalet for a new start. Ed plays the perfect love interest and probably continued to swoon fans that will watch or have watched the movie.

5 Matthew Settle – Rancid (2004)

Matthew Settle has been making a name for himself since the mid-1990s, and when he scored the role of Rufus Humphrey on Gossip Girl, it was a perfect fit. Prior to the successful series, he starred in a film called Rancid, taking the role of James Hayson, a successful-writer-turned freelancer.

He experienced a traumatic experienced which dulled his world and after going to a high school reunion, his world turns upside down. Embroiled in deceit, an old flame, and murder, James must tread lightly and trust in himself once again.

4 Taylor Momsen – How The Grinch Stole Christmas (2000)

Taylor Momsen, also known as Jenny Humphrey, was just a young teen from Brooklyn who wanted to fit in with the rest of the girls at Constance. But, before she became Jenny, she was Cindy Lou Who in the live adaptation of the Christmas classic, How the Grinch Stole Christmas.

She may look unrecognizable as a little girl, and like her transformation today, she’s quite the chameleon. She played the perfect Cindy Lou Who, who tries to tell the people of Whoville that the Grinch, played by Jim Carrey, isn’t so bad after all. Without a doubt, How the Grinch Stole Christmas will go down as one of the best holiday movies from the 2000s.

3 Jessica Szohr – Art Machine (2012)

Another young woman from Brooklyn, who is close with the Humphrey family, is Vanessa Abrams, played by Jessica Szohr. She’s a bit of a hipster and became a reoccurring character in the Gossip Girl series.

The same year that Gossip Girl ended, Jessica starred in the movie, Art Machine. It’s a comedy about a child prodigy painter named Declan Truss, played by Joseph Cross, who is lacking inspiration. He meets Cassandra, who is part of a freethinking group in the art world that Declan discovers. Jessica is an excellent choice for this role and makes it her own.

2 Connor Paolo – Stake Land (2010)

Eric van der Woodsen, played by Connor Paolo, is Serena’s younger brother, who has a troubled past and is coming into his own as a homosexual young man. Two years before Gossip Girl ended, Connor starred in Stake Land, a sci-fi drama about a vampire hunter and his young protégé named Martin, played by Connor.

Martin was a normal teenage boy before the world collapsed, and a vampire epidemic swept across the nation. He’s assisted by a man named Mister, played by Nick Damici, to get to Canada, the “New Eden” of the world. Stake Land provides good acting, with plenty of suspense to keep the viewers going. In fact, Stake Land is one of several underrated vampire movies that should get more recognition.

1 Margaret Colin – Independence Day (1996)

Eleanor Waldorf is Blair’s mother and is a successful fashion designer who is rarely around. While she’s hard to like at times, she does have her moments and Margaret Colin portrays this upper-crust character well.

Before Margaret joined the Upper East Side, she starred in Independence Day as Constance Spano, the U.S. President’s White House Communication Director and soon-to-be ex-wife of David Levinson, played by Jeff Goldblum. Independence Day is stacked with an A-list cast and an action-packed storyline about mankind’s survival and an evil alien invasion. Independence Day is one of the great alien invasion movies that will be hard to beat and is a true 1990s gem.