- 2008: Cast in the television adaptation of "The Memory Keeper's Daughter" (Lifetime)
- 2007: Co-starred in the Garry Marshall directed "Georgia Rule"
- 2007: Portrayed the father in "Gracie," a movie inspired by events in the lives of Elisabeth and Andrew Shue
- 2005: Played the eldest son, who brings his girlfriend (Sarah Jessica Parker) home to meet his family, in the holiday comedy "The Family Stone"
- 2005: Starred with Debra Messing in the romantic comedy "The Wedding Date"
- 2004: Starred with Josh Lucas in the dramatic thriller "Undertow"
- 2003: Cast in the ensemble "The Safety of Objects"
- 2002: Had comedic turn as Jack Nicholson's prospective son-in-law in "About Schmidt"
- 2001: Appeared in Nicole Holofcener's "Lovely & Amazing," opposite wife Catherin Keener and Brenda Blethyn
- 2001: Re-teamed with Rudolph for "Investigating Sex"
- 2000: Shared the screen with film legend Paul Newman and Linda Fiorentino in "Where the Money Is"
- 2000: First film with writer-director Alan Rudolph, "Trixie"
- 1998: Starred with Patricia Arquette and Don Johnson as "a murderous, adulterous, ambitious family" in the black comedy "Goodbye Lover"
- 1997: Portrayed the prospectiv bridegroom caught between Julia Roberts and Cameron Diaz in "My Best Friend's Wedding"
- 1996: Appeared briefly in Anjelica Huston's "Bastard Out of Carolina" (Showtime) as Jennifer Jason Leigh's sweet-tempered husband
- 1996: Played a young upstart mobster in Robert Altman's "Kansas City"; Buscemi also in cast
- 1996: Re-teamed with DiCillo for "Box of Moonlight," playing a hostile grease monkey
- 1995: Served as associate producer of DiCillo's "Living in Oblivion," an expanded version of "Scene Six, Take One"
- 1995: Played Wynona Ryder's beau in "How to Make an American Quilt"
- 1994: First collaboration with director Tom DiCillo, the short "Scene Six, Take One"; played Wolf, the cinematographer, to Buscemi's director
- 1993: Wrote the song "Someone Else's Used Guitar" for Peter Bogdanovich's "The Thing Called Love"; also acted in the movie
- 1993: Portrayed the clueless boyfriend of Bridget Fonda's trained assassin in "Point of No Return"
- 1993: Acted with Steve Buscemi for the first time in "The Last Outlaw" (HBO)
- 1993: Re-teamed with Shepard for "Silent Tongue"
- 1992: First leading role in a feature, "Where the Day Takes You"
- 1990: Acted with Sam Shepard in Michael Fields' "Bright Angel"
- 1989: Played a gay man who dies from an AIDS-related illness in "Longtime Companion"
- 1988: Feature debut, Blake Edwards' "Sunset"
- 1988: Joined an all star cast for Christopher Cain's "Young Guns"
- 1986: TV debut in the CBS TV-movie "Sin of Innocence"
- Raised in Alexandria, Virginia




