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She has maintained that her parents gave her a normal upbringing and, despite their criminal past, has stated, "It made me realize that you can't judge anyone—especially your parents—for what they've done in their past, because people change." When she was 11 years old, Meester and her siblings moved with their mother to New York City.She attended the Professional Children's School and began working as a model with Wilhelmina, booking a Ralph Lauren campaign shot by Bruce Weber, and working with then-photographer Sofia Coppola.In October 2010, Meester said she had been working with a band called Check in the Dark and had been writing for the last six months after being inspired by Country Strong.She revealed her influences, "I love Neil Young and Joni Mitchell, that style of music, and as far as songwriting I think that's where my heart is." Vera Wang selected her to be the face of the fragrance Lovestruck in 2011, stating that Meester's "beauty, talent and spirit will inspire all the young women that I hope will enjoy this passionate, new young fragrance." while Los Angeles Times wrote, "[Meester's] performance often has the feeling of a sports car in neutral.In 2009, she featured on Cobra Starship's "Good Girls Go Bad", which charted in the top ten of the Billboard Hot 100, and released her first single "Somebody to Love" on the Universal Republic label.She released a second single "Your Love's a Drug" in 2010.However, it was important that Serena was blonde and Blair was brunette, so Meester dyed her hair brown for the role.
It follows the friendship between a lesbian (Meester) and a straight woman (Gillian Jacobs) who begin a new relationship.
Wesley Morris of The Boston Globe described Meester as the best part of the film, writing, "She's just doing Reese Witherspoon's June Carter Cash in Walk the Line with dabs of Miley Cyrus and Kellie Pickler.
But it's not an impersonation; it's a performance with its own comedy and sweetness." For the film, Meester recorded a cover of the song "Words I Couldn't Say" by Rascal Flatts as well as "A Little Bit Stronger" by Sara Evans featured on the film's soundtrack; a promotional single titled "Summer Girl"; and a duet with Garrett Hedlund titled "Give In To Me".
She then appeared opposite Robert Downey, Jr., Robert Duvall, and Vera Farmiga in the David Dobkin-directed comedy-drama film The Judge, which premiered at the Toronto International Film Festival and released in October 2014.
On September 9, 2014, it was announced her debut album, Heartstrings, would be released independently through her own label, Hotly Wanting, on October 28, 2014.