Began going on auditions at age 5 with his older brother, Ben, and they appeared as extras in Field of Dreams and The Good Mother.
Portrayed a young Robert Kennedy in ABC's 1990 miniseries The Kennedys of Massachusetts.
First major movie role was in Gus Van Sant's 1995 satire To Die For, opposite Nicole Kidman; befriended costar Joaquin Phoenix on the set and years later married Phoenix's sister Summer.
Made a name for himself appearing in supporting roles in films such as Chasing Amy, Good Will Hunting and Ocean's Eleven.
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