milestones
Year
Milestone
 
Raised in Alexandria, Virginia
1986 
TV debut, "Sin of Innocence", a CBS TV-movie
1988 
Feature debut, Blake Edwards' "Sunset"
1988 
Joined Emilio Estevez, Charlie Sheen, Kiefer Sutherland, Lou Diamond Philips and Casey Siemaszko as the six cowboys of Christopher Cain's "Young Guns"
1989 
Starred in "Unconquered" (CBS), the true story of Richmond Flowers Jr who overcame illness, a physical handicap and the derision of his classmates to become a world-class hurdler and football star
1989 
Played a gay man and the first character to die of AIDS-related illness in "Longtime Companion"
1990 
Acted with Sam Shepard in Michael Fields' "Bright Angel"
1992 
First leading role in a feature, "Where the Day Takes You"
1993 
Portrayed the clueless boyfriend to Bridget Fonda's trained assassin in "Point of No Return"
1993 
Wrote the song "Someone Else's Used Guitar" for Peter Bogdanovich's "The Thing Called Love"; also credited as song performer on it and four other tunes, as well as acting in the movie
1993 
Reteamed with Shepard, portraying the prototypical Shepard "son" character in "Silent Tongue", helmed and scripted by Shepard
1993 
Acted with Steve Buscemi for the first time in "The Last Outlaw" (HBO)
1994 
First collaboration with director Tom DiCillo, the short "Scene Six, Take One", playing Wolf, the cinematographer, to Buscemi's director; second film with wife Catherine Keener
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"
1996 
Reteamed with DiCillo and Keener for "Box of Moonlight", portraying a hostile grease monkey
1996 
Portrayed young upstart mobster in Robert Altman's atmospheric but dramatically lackluster "Kansas City"; Buscemi also in cast
1996 
Appeared briefly in Anjelica Huston's "Bastard Out of Carolina" (Showtime) as Jennifer Jason Leigh's sweet-tempered husband who expires in a freak auto mishap
1997 
Portrayed the prospectiv bridegroom caught between Julia Roberts and Cameron Diaz in "My Best Friend's Wedding"
1998 
Starred with Patricia Arquette and Don Johnson as "a murderous, adulterous, ambitious family" in the black comedy "Goodbye Lover"
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", co-starring with Nick Nolte and Emily Watson (in the title role)
2001 
Reteamed with Rudolph and Nolte on "Investigating Sex"
2001 
Appeared in Nicole Holofcener's "Lovely & Amazing" opposite Catherin Keener and Brenda Blethyn
2002 
Had comedic turn as Jack Nicholson's prospective son-in-law in "About Schmidt"
2003 
Cast in Rose Troche's drama "The Safety of Objects"
2004 
Starred with Josh Lucas in the dramatic thriller "Undertow"
2005 
Starred with Debra Messing in the romantic comedy "The Wedding Date"
2005 
Played the eldest son who brings his girlfriend, Meredith (Sarah Jessica Parker), home to New England to meet his family in the holiday comedy "The Family Stone"
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
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Lauren and Heidi of MTV's "The Hills"
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