Rose to fame for his roles in the 1985 film Explorers and the 1989 film Dead Poets Society. He also gained notoriety for playing Jesse in Richard Linklater's Before Sunrise series. In 2001, he received a Screen Actors Guild Award nomination for his portrayal of Jake Hoyt in Training Day and his role in the 2014 film Boyhood earned him a Golden Globe nomination for Best Supporting Actor.
He was featured in White Fang as the boy who comes to know the wild wolf.
He starred with Winona Ryder in Reality Bites.
In his youth, he aspired to become a writer but developed a love for acting after starring in a school production of Saint Joan. Later in life he would fulfill his wish and write novels.
He married actress and co-star, Uma Thurman in 1998. They separated in 2003. He has three daughters named Maya, Clementine and Indiana and a son named Indiana.