How Many Movies Have Ansel Elgort And Shailene Woodley Done Together?

Whether they're playing brother and sister coming of age in a dystopian hellscape or whether they are two teens living with and dying from cancer who fall hopelessly in love with one another, actors Ansel Elgort and Shailene Woodley have proven they have chemistry to spare.

As 2021 drew to a close, Elgort thrilled audiences as a triple threat, displaying his acting, singing, and dancing skills in the Steven Spielberg remake of the Stephen Sondheim-Leonard Bernstein musical, "West Side Story," which is of course based on a centuries old story by The Bard himself, William Shakespeare. Taking a page from "Romeo and Juliet," "West Side Story" tells the tale of two star-crossed lovers who are only parted by death and Elgort plays the romantic lead, Tony (via IMDb).

Woodley began acting at a young age and by the time she was just 8 years old, she made her TV movie debut in "Replacing Dad," where she worked with legendary actress Tippi Hedren. By high school is where Woodley truly gained fame, starring for five seasons on the series "The Secret Life of the American Teenager," but it was a supporting role in George Clooney's "The Descendants" in 2011 that earned her a Golden Globe nomination (via Biography), as well as the ticket to more high profile Hollywood roles, and that's when Elgort and Woodley's paths began to cross.

Two movies made their box office debuts in 2014 that paired Ansel Elgort and Shailene Woodley. First, there was "Divergent," the first in a series of dystopian movies based on the books by Veronica Roth about a future where people choose a destiny already spelled out for them, but Woodley's Tris learned she doesn't fit into any destiny of "faction" and the story grows from there (via Rotten Tomatoes). Woodley was the star of this vehicle and Elgort had a supporting role as Woodley's brother, who first seems to turn against her character, but then tries to save her.

That same year, "The Fault In Our Stars" became a teen hit after millions of young adults read the book of the same name by John Green. Woodley and Elgort played Hazel and Augustus, two teens dealing with cancer who meet at a support group and fall madly in love with one another (via John Green Books). When Augustus dies unexpectedly and Hazel lives on, there's not a dry eye in the house either when reading the novel or watching the movie.

After playing tragic star-crossed lovers, Ansel Elgort and Shailene Woodley shared the screen two more times for sequels to "Divergent" titled "Insurgent" and "Allegiant," in which both Elgort and Woodley's brother-sister characters learn that their entire life has been nothing but a social experiment and even their own mother knew it.

Elgort and Woodley were set to star in another movie in the "Divergent" franchise called "Ascendent," but when "Allegiant" had poor box office returns, the plans were scrapped. A TV movie idea was also floated around, but none of the stars were interested in a TV version, so fans never got to see the final installment of the "Divergent" series. According to Screen Rant, Woodley truly wanted to play out the end of Tris' saga, but she couldn't see it happening on the small screen. She was so disappointed that "Ascendent" never made it to the big screen that she even considered quitting acting.