Acted in a junior high school production of "Meet Me in St. Louis"
Professional stage debut, "St. Joan" at the McCarter Theatre in Princeton, NJ
Feature acting debut, Joe Dante's "Explorers"
Returned to features with a well-received supporting role as the baby-faced Todd in Peter Weir's "Dead Poets Society"
Played Ted Danson's son and Jack Lemmon's grandson in "Dad," a film based on a William Wharton novel
Off-Broadway debut, New York Shakespeare Festival production of "Casanova"
Visited the Steppenwolf Theater in Chicago during a cross-country drive with playwright-actor Jonathan Marc Sherman and actor Josh Hamilton; inspired to start a theater group
Started a reading series in NYC with Sherman and Hamilton
Co-founded Malaparte, a nonprofit theater group; served as artistic director; "Dead Poets Society" co-star Robin Williams was among the notables providing funding; company included Robert Sean Leonard, Frank Whaley, Steve Zahn and Hamilton; eventually disbanded
Broadway debut, National Actors Theater production of Chekhov's "The Seagull"
Played a reluctant platoon leader in "A Midnight Clear"; also featured Steppenwolf's co-founder Gary Sinise and friend Frank Whaley; second film based on a Wharton novel
Wrote, directed and edited the short film "Straight to One"
Acted in Jonathan Marc Sherman's "Sophistry" at NYC's Playwrights Horizon
Co-starred in Ben Stiller's feature directorial debut "Reality Bites"; also helmed Lisa Loeb's music video "Stay," a featured single from the soundtrack; Steve Zahn also acted in film
Theatrical directorial debut, "Wild Dogs!"; officially opened the first full season of Malaparte
Acted opposite Julie Delpy in Richard Linklater's romantic cult classic "Before Sunrise"
Acted in the Steppenwolf Theater Company production of Sam Shepard's "Buried Child" in Chicago; project reunited him with Sinise who directed
Published first novel <i>The Hottest State</i>
Starred in the sci-fi thriller "Gattaca," written and directed by Andrew Niccol; co-starred with future wife Uma Thurman
Portrayed the Pip-like Finn in the contemporary remake of Dickens' "Great Expectations"
Appeared as Jess Newton, the charming drunken brother in Linklater's "The Newton Boys"
Played Ishmail, the one-armed journalist in love with a Japanese woman in "Snow Falling on Cedars"; adapted from David Guterson's 1994 novel about a doomed interracial romance
Cast in small role as a concerned guidance counselor in Frank Whaley's feature directorial debut "Joe the King"
Acted in Williamstown Theatre Festival staging of Tennessee Williams' "Camino Real"
Starred as Michael Almereyda's slacker "Hamlet"; Zahn played Rosencrantz
Again collaborated with Linklater on the digitally-shot "Tape," co-starring Robert Sean Leonard and Uma Thurman
Returned to the NYC stage as one of the stars of the Manhattan premiere of Sam Shepard's play "The Late Henry Moss"
Cast as a rookie cop teamed with an amoral partner (Denzel Washington) in "Training Day"; earned an Oscar nomination for Best Supporting Actor
Feature directorial debut, "Chelsea Walls," based the film on Dylan Thomas' 1954 radio drama "Under Milkwood"; co-starred wife Uma Thurman and friends Leonard, Whaley, and Zahn
Re-teamed with Whaley in "The Jimmy Show"; written and directed by Whaley
Guest starred on the ABC series "Alias" as a captured CIA agent whose allegiances may have shifted
Reunited with director Richard Linklater and Julie Delpy for "Before Sunset" once again portraying Jesse (Hawke) and Celine (Delpy) who are reunited nine years after they first met; also co-wrote screenplay; received an Independent Spirit Award nomination for Best Screenplay; received an Oscar nomination for Best Adapted Screenplay
Portrayed an Interpol agent, chasing an arms dealer (Nicolas Cage) in Andrew Niccol's "Lord of War"
Cast as part of an ensemble in Linklater's "Fast Food Nation"
Cast in "The Coast of Utopia," playing Mikhail Bakunin; received a Tony Award nomination
Wrote and directed "The Hottest State," based on his novel of the same name; also co-starred (debuted at the 2006 Venice Film Festival)
Co-starred with Philip Seymour Hoffman in Sidney Lumet's "Before the Devil Knows You're Dead"
Acted with Mark Ruffalo in the crime drama "What Doesn't Kill You"
Cast as Edward Dalton, a vampire researcher in the sci-fi film "Daybreakers"
Re-teamed with Antoine Fuqua for "Brooklyn's Finest"
Co-starred with Kristin Scott Thomas in Parisian-set thriller "The Woman in the Fifth"
Starred in found-footage thriller "Sinister"
Starred in "Before Midnight," his third Linklater/Delpy collaboration
Featured in the horror hit "The Purge"