He starred in the 1990s films White Fang (1991) and its sequel (1994); Reality Bites with Winona Ryder (1994), Gattaca with Uma Thurman (1997), and Great Expectations with Gwyneth Paltrow (1998).
During the 2000s, Hawke starred in numerous blockbuster films including Training Day opposite Denzel Washington (2001), Taking Lives with Angelina Jolie (2004), Lord of War with Nicolas Cage (2005), Before the Devil Knows You're Dead with Philip Seymour Hoffman (2007), and Brooklyn's Finest with Richard Gere (2009).
The following years, Hawke co-starred in the films Maggie's Plan (2015), Born to Be Blue (2015), The Magnificent Seven (2016), Valerian and the City of a Thousand Planets (2017), Juliet, Naked (2018), The Black Phone (2021) and The Northman (2022).
In addition to his film work, Hawke has appeared in many theater productions, making his Broadway debut in 1992 in Anton Chekhov's The Seagull, and was nominated for a Tony Award for Best Featured Actor in a Play in 2007 for his performance in Tom Stoppard's The Coast of Utopia.
In 2010, Hawke directed Sam Shepard's A Lie of the Mind, for which he received a Drama Desk Award nomination for Outstanding Director of a Play.