Her second single "Your Love's a Drug" was released in 2011.Meester has also recorded songs for various soundtracks.
Also in 2010, she starred with Gwyneth Paltrow and Garrett Hedlund in the country music drama Country Strong.
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).
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.
Following this, she made her film debut in Hangman's Curse (2003), based on the bestselling book by Frank Peretti.