Leighton Master embodies the trifecta of artistry with acting, singing, and theater roles in her repertoire. Since her drama-filled, headband-wearing role as Blair Waldorf in The CW’s Gossip Girl, based on the YA novel series by Cecily von Ziegesar, Meester has gone on to star in a wide variety of roles. Indeed, Meester’s time in the spotlight has earned her spots alongside Selena Gomez in Monte Carlo and even landed her on Broadway in a play adapted from John Steinbeck’s Of Mice and Men.
Her most recent role was in the new Netflix Original thriller about a girls’ trip gone wrong The Weekend Away based on the novel by Sarah Alderson. While the film received mixed reviews, most would agree that Meester’s acting was flawless. Meester also recently starred in a recurring role on Hulu’s How I Met Your Father, which just finished its first season. At this time, the actress does not officially have any upcoming films or shows, but rest assured she will grace our screens once again. In the meantime, here are some of Leighton Meester’s best performances, ranked.
8 The Roommate
Sarah, played by Minka Kelly, and Rebecca, played by Meester, are assigned as freshman roommates. Where Sarah is outgoing and nice, Rebecca is quiet and reserved. The two become friendly and Sarah tries to include her roommate unaware that Rebecca is slowly becoming obsessed with Sarah.
In The Roommate, Leighton Meester is perhaps one of the best parts of the movie. Her character is obsessive, a stalker, and all-around unhinged, which Meester expertly portrays. The film itself had a lot of potential to be a compelling thriller, but ultimately fell flat. Meester’s screen time is arguably the only reason the film is worth watching.
7 Country Strong
Full of drama, country music, and relationships, Country Strong looks at the lives of three people: an alcoholic, washed-up diva, a new rising country boy, and a pageant queen turned singer. The love triangle between the three causes drama and threatens the stardom of the three forced to tour together.
Another flop that had potential, Country Strong showcases the musical talent of Meester as a naive country singer. Starring alongside Garret Hedlund, Gwyneth Paltrow, and Tim McGraw, Meester’s beauty pageant and sweetheart personality stands out against the drama-filled characters. Meester also does her own singing in the movie, and had a few of her songs hit the top charts back in 2010 when the film was released.
6 Monte Carlo
Grace, Emma, and Meg, played by Selena Gomez, Katie Cassidy, and Leighton Meester, go on vacation to Paris, which turns into an experience they will never forget. Grace is mistaken for a famous heiress and brings along Emma and Meg as she lives out the heiress’ life for a few days.
In the family-friendly film Monte Carlo, Meester plays an uptight sister who lives to follow the rules. When forced on a vacation with her stepsister, she’s the one who ends up learning how to let loose. Meester’s transformation from rule-follower to adventure seeker is another example of her diversity in roles.
5 The Weekend Away
In Meester’s most recent role, she stars in a Netflix Original Movie about a weekend trip with her best friend that turns deadly after she is accused of killing her best friend. As Meester’s character tries to piece together her fuzzy memory from the night before, she finds herself looking more guilty to the police.
This film portrayed Meester in a new light by adding a thriller to her filmography. Full of twists and seemingly obvious conclusions, Meester’s character has to become a detective to clear her name and to find out more about her best friend’s behavior. While the film received mixed reviews, the movie does display another compelling performance by Meester.
4 The Judge
Hank is a big city lawyer who is called home after his mother dies. While home, his father, the judge, is accused of murder. Hank investigates and, along the way, meets up with his high school sweetheart and reconnects with his family.
In The Judge, Meester plays the supporting role of Carla Powell, a young bartender who makes out with Hank, played by Robert Downey Jr., after meeting at the bar she works at. It turns out that Carla is the daughter of his old high school sweetheart, which leads to an awkward encounter when the three meet. Meester’s screen time does not amount to much in this film, but her ability to stand beside powerhouse actors like Downey Jr. and Vera Farmiga shows that she can hold her own on screen.
3 Like Sunday, Like Rain
Like Sunday, Like Rain follows the lives of two musicians: Reggie who is a 12-year-old prodigy, and Eleanor who is a young woman that is struggling with her life. The lighthearted story is about acceptance and discovering one’s self.
Meester’s character, Eleanor, is a mess. She is going through a breakup and was fired from her waitressing job when she meets Reggie. The two form a unique friendship as she is one of the few who can really resonate with him. Reggie’s cynicism and Eleanor’s kindness give viewers an onscreen duo to love and a movie for all ages.
2 Single Parents
A group of single parents come together and form their own support system as they struggle to both raise their children and find new relationships. Each parent and their children have their own personality traits, from a clingy son to an overwhelmed parent. Set as a comedy, each episode can be watched in under 30 minutes.
Single Parents ran for two seasons from 2018-2020 on ABC. Reviews stated that it was easy to get invested in a diverse group of characters. While this is a comedy, the show is also full of life lessons. Meester plays a single mom to a very clingy son.
1 Gossip Girl
Gossip Girl follows a group of privileged New Yorkers from high school to college and then to their adult lives. An online blogger called Gossip Girl, reports on the group leaving no secret left unturned. Full of drama, lies, fashion, and romance, Gossip Girl gives its viewers an insight into a crazy New York life.
In arguably one of her most famous roles, Meester plays Blair Waldorf, a rich, manipulative, yet loyal Upper East Sider. Throughout the show’s six seasons, Blair has one of the best character arcs as we get to watch her find confidence in herself. The TV-14 rated show ran from 2007-2012 on The CW and is still streamed constantly through Netflix. Meester’s mean-girl attitude is very different from her personality in her real-life, which makes her acting that much better.
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