- 2007: Starred in the indie drama "Grace Is Gone," playing a father who embarks on a road trip with his two daughters after his wife is killed in the line of duty in Iraq; premiered at Sundance
- 2007: Once again teamed with Dutch filmmaker Menno Meyjes on "The Martian Child"
- 2005: Played a simple-minded attorney who tries to steal money from his mob bosses in the "Ice Harvest," directed by Harold Ramis
- 2003: Co-starred in James Mangold's psychological thriller "Identity"
- 2002: Starred in the Nazi drama feature "Max," written and directed by Menno Meyjes
- 2001: Teamed romantically onscreen with Kate Beckinsale in "Serendipity"
- 2000: Reteamed with Frears for "High Fidelity," playing an immature record-obsessed thirtysomething; based on Nick Hornby's acclaimed novel
- 1999: Starred in the western "The Jack Bull," written by his father Dick Cusack
- 1999: Played Nelson Rockefeller in Tim Robbins' "Cradle Will Rock"
- 1999: Cast as puppeteer, Craig Schwartz who discovers a portal into the brain of the titular movie actor in Spike Jonze's experimental film "Being John Malkovich"
- 1999: Played a high-strung air traffic controller in Mike Newell's "Pushing Tin"
- 1998: Was featured in the ensemble cast of Terrence Malick's sweeping war drama "The Thin Red Line"
- 1997: Co-produced, scripted and starred in the sharp, high-school reunion set action-comedy "Grosse Point Blank"
- 1997: Starred in Clint Eastwood's uneven screen adaptation of "Midnight in the Garden of Good and Evil"
- 1997: Voiced the male lead Dimitri in the animated feature "Anastasia"
- 1997: Starred as a US Marshal in the summer action blockbuster "Con Air"
- 1996: Played a young, idealistic deputy mayor of New York in the political drama "City Hall"
- 1994: Co-starred in Alan Parker's satire "The Road to Wellville"
- 1994: Reteamed with Woody Allen with a featured role as a playwright in "Bullets Over Broadway"
- 1993: Had a supporting role in the period drama "Map of the Human Heart"
- 1992: Had a small role in Tim Robbins' directorial debut "Bob Roberts"
- 1992: Formed the film production arm of New Crime Productions with Paramount Pictures
- 1992: Was featured with a strange cameo role in the offbeat comedy "Roadside Prophets"
- 1991: Had a small role in "Shadows and Fog," his first film with Woody Allen
- 1991: Cast as an ethically corrupt political climber opposite an idealistic James Spader in the drama "True Colors"
- 1990: Played Anjelica Huston's con artist son in Stephen Frears' "The Grifters"
- 1989: Last teen role as cult icon Lloyd Dobler in Cameron Crowe's "Say Anything"; sister Joan also starred in film
- 1989: Starred as a nuclear physicist working on the atomic bomb in World War II in "Fat Man and Little Boy"
- 1988: First adult role, starring opposite Tim Robbins in the zany comedy "Tapeheads"
- 1988: Featured in the ensemble "Eight Men Out," John Sayles film of the 1919 Black Sox scandal
- 1987: Starred in the inane comedy "Hot Pursuit"
- 1986: Founded New Crime Productions, a Chicago based theater company
- 1986: Had a memorable cameo in "Stand By Me," helmed by Rob Reiner
- 1985: Was featured in Disney's "The Journey of Natty Gann"
- 1985: Starred as a heartbroken teen in the comedy "Better Off Dead"
- 1985: Played first leading role in Rob Reiner's "The Sure Thing"; first screen teaming with Tim Robbins
- 1984: Was one of the main nerds featured in "Sixteen Candles"; sister Joan also appeared in film
- 1983: Screen acting debut as a prep school student in the coming-of-age comedy "Class"
- 1982: Went on first feature audition at age 16 for "Class"
- Was appearing in industrial films, doing voiceovers in commercials and acting in radio spots by the age of twelve
- Directed a stage production of Hunter S Thompson's "Fear and Loathing in Las Vegas"




