
In 2008, Woodley was cast in the lead role of Amy Juergens in The Secret Life of the American Teenager (2008) and in 2011 she had her big screen breakthrough when she appeared in Alexander Payne's The Descendants (2011), opposite George Clooney. Her performance in the role of Alexandra King brought critical acclaim and recognition by the movie industry. She won an Independent Spirit Award and the 2012 MTV Movie Awards Breakthrough Performance Award, as well as a Golden Globe nomination.
In October 2012, it was announced that Woodley was offered the role of Mary Jane Watson in The Amazing Spider-Man 2. On June 19, 2013, it was announced that she was cut from the film. Director Marc Webb told The Hollywood Reporter that the cut was "a creative decision to streamline the story and focus on Peter and Gwen and their relationship," and that everyone loved working with Woodley.

Woodley starred as Tris Prior in the film Divergent, an adaptation of Veronica Roth's best-selling young adult novel of the same name, and the first installment in The Divergent Series; it was released on March 21, 2014. The film received mixed reviews, but Woodley's performance as Tris received a positive reception.
Woodley will reprise her role as Tris in the second installment in The Divergent Series, titled The Divergent Series: Insurgent, which began filming on May 27, 2014 and has a release date of March 20, 2015. She will reprise her role again in the two-part finale of the franchise, The Divergent Series.