Since her breakthrough role in the Divergent series, Woodley has embraced more mature roles. She delivers a raw and sincere performance in the movie The Spectacular Now, as a free spirit that defies family expectations.

She then starred in the biographical thriller Snowden, as Lindsay Mills, an American activist who leaked classified CIA information.

The Fault in Our Stars

The Fault in Our Stars is a poignant, heart-affecting tragic love story that takes us on the journey of two teenagers facing cancer and finding each other. Shailene Woodley and Ansel Elgort both give exceptional performances and help to elevate this spacemov film above the usual YA adaptations. The chemistry between the two is undeniable.

The film is based on the bestselling book by John Green and follows the story of Hazel Grace Lancaster, a 16 year-old bookworm who is diagnosed with terminal cancer. She comes perilously close to death as a preteen, but an experimental treatment allows her to live a mostly normal life. However, she now carries around an oxygen tank and is constantly reminded of the fragility of her life. Despite her condition, she finds a sense of purpose and meets the love of her life in the form of Gus Waters, a boy at her cancer support group. He charms her with his acerbic wit and their shared love of books.

Endings, Beginnings

Endings, Beginnings is a beautiful and raw depiction of the harder side of love. Woodley proves she has a knack for vulnerable, haunted roles – her performances in Big Little Lies and The Spectacular Now are reminiscent of this indie drama from Drake Doremus (Like Crazy). While it may move slowly, this film will definitely stay with you after you leave the theater.

After a bad breakup, 30-something Daphne (Shailene Woodley) moves into her sister Billie’s guest house and pledges to be sober and celibate for six months. But at a New Year’s Eve party, she finds herself drawn to two different men: the stable Jack (Jamie Dornan) and free-spirited Frank. When they reveal they’re close friends, she becomes caught in a toxic love triangle.

Divergent

After gaining notoriety on television with the 2008 series The Secret Life of the American Teenager, Woodley hit the big time with 2014’s teen romantic drama The Fault in Our Stars and the science fiction franchise Divergent. Her performance as Tris Prior fended off the machinations of an evil government faction, and the film’s success landed her roles in the sequels Insurgent (2015) and Allegiant (2016). Along the way, she’s worked with an impressive cast including a roster of Oscar winners, such as Nicole Kidman, Reese Witherspoon, and Sebastian Stan.

Divergent might seem like a carbon copy of The Hunger Games, with its dystopian societies divided into five factions and action-packed adventure, but it manages to distinguish itself with a tough heroine, solid action sequences, and a world that might credibly shake a teenager. That said, the film’s directors—Neil Burger and Robert Schwentke—struggle to make it all work, with clunky results.

White Bird in a Blizzard

Woodley has made a series of smart, sensible post-YA career moves: taking roles opposite multiple A-listers in HBO’s critically acclaimed Big Little Lies (which was recently renewed for a second season), starring in the Netflix romance The Last Letter from Your Lover for director Augustine Frizzell, and not hurriedly signing up for big-ticket tentpole movies that would drown out her empathetic sensibility. She’s also embracing weightier work, most recently appearing in the film Snowden as Lindsay Mills, the girlfriend of Edward Snowden, who revealed covert CIA operations tracking the public through their cell phones.

In the James Ponsoldt drama The Spectacular Now, Woodley stars alongside Miles Teller and other great actors like Brie Larson in a story about young love and discovering who you are as an individual through your surrounding relationships. It earned a 71% rating on Rotten Tomatoes and helped establish Woodley as a serious leading lady.

The Descendants

One of Shailene Woodley’s best films is The Descendants, which she co-starred in with veteran actor George Clooney. Based on a book, this film follows a lawyer who inherits a large chunk of Hawaiian land. He must decide whether to keep the property unspoiled or sell it to please his greedy family.

The Descendants is a smart and absorbing drama that is both humorous and sad. It won an Oscar for Best Adapted Screenplay and two Golden Globes for both the movie and George Clooney. The cast is incredible and the story is relatable for everyone.