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In 2015, he has starred in the first season of the FOX television series Wayward Pines, for which he was nominated for a Saturn Award.

In 1978, Jane Bernstein and a friend were helping director Jonathan Kaplan cast the violent teen drama Over the Edge when they found Dillon cutting class at Hommocks Middle School in Larchmont.

In the 2000s, he made his directing debut with City of Ghosts (2002) and went on to star in the films Factotum (2005), You, Me and Dupree (2006), Nothing but the Truth (2008), Sunlight Jr. For Crash (2004), he won an Independent Spirit Award and was nominated for a Golden Globe Award and the Academy Award for Best Supporting Actor.

In 2018, Dillon played the lead role in the Lars von Trier thriller The House That Jack Built.In 2005, Dillon co-starred in Disney's Herbie: Fully Loaded and on March 11, 2006 hosted Saturday Night Live, in which he impersonated Greg Anderson and Rod Serling in sketches.Dillon starred in the comedy You, Me and Dupree, opposite Kate Hudson and Owen Wilson. On September 29, 2006, Dillon was honored with the Premio Donostia prize in the San Sebastián International Film Festival.In 1989, Dillon won critical acclaim for his performance as a drug addict in Gus Van Sant's Drugstore Cowboy.Dillon continued to work in the early 1990s with roles in films like Singles (1992).

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