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." On September 9, 2014, it was announced her debut LP Heartstrings would be released independently through her own label, Hotly Wanting, on October 28, 2014.
But it's not an impersonation; it's a performance with its own comedy and sweetness." Though the film mainly received negative reviews, Meester's portrayal was praised by critics.Entertainment Weekly found she was the only one to bring "the slightest trace of something fascinating to her role," while Los Angeles Times wrote, "[Meester's] performance often has the feeling of a sports car in neutral.Her debut album, Heartstrings, was independently released in 2014.She has also modeled, having been the face of brands such as Jimmy Choo, Herbal Essences, At the time of her birth, her mother was serving time in a federal prison for her involvement in a drug ring that smuggled marijuana from Jamaica to the United States.She has also appeared in the films Killer Movie (2008), Country Strong (2010), The Roommate (2011), Monte Carlo (2011), The Oranges (2011), and The Judge (2014).
Meester made her Broadway debut in Of Mice and Men (2014).
Meester subsequently appeared in the television film The Haunting of Sorority Row, and had a role in the ensemble comedy-drama film Remember the Daze.
She also appeared in the horror-thriller film Killer Movie in 2008.
She then appeared in Tarzan, which ran for only eight episodes.
Meester started to book guest roles in other series such as Crossing Jordan, 8 Simple Rules, 7th Heaven, Veronica Mars, 24, and Entourage.
She was able to give birth to Leighton in a hospital and nurse her for three months in a halfway house, before returning to prison to complete her sentence, after which Leighton's grandmother cared for her.