The Bride!
as Jake Wiles
Mar 4, 2026
Pet Shop Days
Oct 22, 2025
September 5
as Roone Arledge
Nov 7, 2024
Coup!
as Floyd Monk
Aug 2, 2024
Memory
as Saul
Dec 22, 2023
The Survivor
as Emory Anderson
Apr 7, 2022
The Batman
as District Attorney Gil Colson
Mar 1, 2022
The Lost Daughter
as Professor Hardy
Dec 15, 2021
The Guilty
as Henry Fisher (voice)
Sep 24, 2021
Best Summer Ever
as Camera Man
Oct 10, 2020
Human Capital
as Quint Manning
Jul 17, 2020
Mr. Jones
as Walter Duranty
Oct 3, 2019
The Sound of Silence
as Peter Lucian
Sep 13, 2019
The Lie
as Jay Logan
Sep 13, 2018
Loving Pablo
as Shepard
Dec 14, 2017
Wormwood
as Frank Olson
Sep 1, 2017
Jackie
as Robert Kennedy
Dec 2, 2016
The Magnificent Seven
as Bartholomew Bogue
Sep 14, 2016
Starring Austin Pendleton
as Self
Apr 1, 2016
Experimenter
as Stanley Milgram
Oct 16, 2015
Black Mass
as Brian Halloran
Sep 17, 2015
Pawn Sacrifice
as Father Bill Lombardy
Sep 16, 2015
Ladygrey
as Samuel
May 6, 2015
Valley Uprising
as Self - Narrator (voice)
Sep 1, 2014
Night Moves
as Harmon
Apr 23, 2014
Lovelace
as Chuck Traynor
Aug 8, 2013
Blue Jasmine
as Dwight
Aug 1, 2013
Very Good Girls
as Fitzsimmons
Jan 22, 2013
Robot & Frank
as Robot (voice)
Aug 24, 2012
Green Lantern
as Hector Hammond
Jun 14, 2011
Knight and Day
as Fitzgerald
Jun 15, 2010
Jake Gyllenhaal Challenges the Winner of the Nobel Peace Prize
as Alan Troy (archive footage)
Jan 1, 2010
An Education
as David Goldman
Oct 29, 2009
Mama's Little Devils: Bad Seeds and Evil Children
as Self
Oct 27, 2009
Orphan
as John
Jul 24, 2009
In the Electric Mist
as Elrod Sykes
Apr 15, 2009
Elegy
as Kenneth Kepesh
Aug 8, 2008
The Mysteries of Pittsburgh
as Cleveland Arning
Jan 20, 2008
Indie Sex: Teens
Jan 4, 2008
Rendition
as Alan Smith
Sep 7, 2007
Year of the Dog
as Newt
Apr 13, 2007
High Falls
as Pedro
Jan 19, 2007
"Jarhead" Diaries
as Self
Mar 7, 2006
Jarhead: Background
as Self
Mar 7, 2006
Jarhead
as Alan Troy
Nov 4, 2005
Flightplan
as Carson
Sep 22, 2005
The Skeleton Key
as Luke Marshall
Jul 29, 2005
The Dying Gaul
as Robert Sandrich
Jan 20, 2005
Kinsey
as Clyde Martin
Sep 4, 2004
Garden State
as Mark
Jul 28, 2004
Shattered Glass
as Charles 'Chuck' Lane
Nov 14, 2003
Death of a Dynasty
as Brendon III
May 7, 2003
Empire
as Jack
Dec 6, 2002
Unconditional Love
as Window Washer
Aug 23, 2002
K-19: The Widowmaker
as Vadim Radtchinko
Jul 19, 2002
The Salton Sea
as Jimmy the Finn
Feb 12, 2002
The Center of the World
as Richard Longman
Apr 19, 2001
Housebound
as Mignon
Sep 2, 2000
The Cell
as Julia Hickson's Fiancee (uncredited)
Aug 18, 2000
Boys Don't Cry
as John Lotter
Sep 2, 1999
Desert Blue
as Billy Baxter
Jun 4, 1999
Freak City
as Cal Jackson
Jan 16, 1999
Another Day in Paradise
as Ty
Dec 30, 1998
The Man in the Iron Mask
as Raoul
Mar 12, 1998
Subway Stories
as Boy No. 1 (segment "Underground")
Jul 24, 1997
Dead Man Walking
as Walter Delacroix
Dec 29, 1995
The Damning of a Country Merchant
Zero K
Road House 2
Erosion
as Christian Andersen
DTF St. Louis
as 'Modern Love' / Christopher Spurce
Mar 1, 2026
Presumed Innocent
as Tommasino 'Tommy' Molto
Jun 11, 2024
Dopesick
as Rick Mountcastle
Oct 13, 2021
Homemade
as Frank
Jun 30, 2020
Interrogation
as David Russell
Feb 5, 2020
The Looming Tower
as Martin Schmidt
Feb 28, 2018
Wormwood
as Frank Olson
Dec 15, 2017
America Divided
as Self
Oct 29, 2016
The Late Show with Stephen Colbert
as Self
Sep 8, 2015
The Slap
as Hector
Feb 12, 2015
Late Night with Seth Meyers
as Self - Guest
Feb 25, 2014
The Tonight Show Starring Jimmy Fallon
as Self
Feb 17, 2014
The Killing
as Ray Seward
Apr 3, 2011
Conan
as Self
Nov 8, 2010
The Tonight Show with Conan O'Brien
as Self
Jun 1, 2009
Indie Sex
as Self
Aug 1, 2007
Cracker
Sep 18, 1997
The Daily Show
as Self
Jul 22, 1996
Late Night with Conan O'Brien
as Self - Guest
Sep 13, 1993
Law & Order
as Josh Strand
Sep 13, 1990
This Week
Nov 15, 1981
Saturday Night Live
as Self - Host, Self - Cameo (uncredited)
Oct 11, 1975
Neuromancer
as John Ashpool
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