Matt Damon
Role: Edward Bell Wilson
Angelina Jolie
Role: Margaret Ann Russell
Robert De Niro
Role: Bill Sullivan
Alec Baldwin
Role: Sam Murach
William Hurt
Role: Philip Allen
Joe Pesci
Role: Joseph Palmi
John Turturro
Role: Raymond Brocco
Billy Crudup
Role: Archibald Cummings
Tammy Blanchard
Role: Laura
Michael Gambon
Role: Dr. Fredericks
Timothy Hutton
Role: Thomas Wilson
John Sessions
Role: Valentin Mironov #1/Yuri Modin
Keir Dullea
Role: Senator John Russell, Sr.
Martina Gedeck
Role: Hanna Schiller
Gabriel Macht
Role: John Russell, Jr.
Lee Pace
Role: Richard Hayes
Eddie Redmayne
Role: Edward Wilson Jr.
Mark Ivanir
Role: Valentin Mironov #2
Yelena Shmulenson
Role: Dollar Woman
Jack Martin
Role: Dollar Little Boy
Anne-Marie Cusson
Role: Philip Allen's Secretary
Robert Bermudez Cordell
Role: Bay of Pigs Voiceover (voice)
David Crommett
Role: Spanish Translator
Michael Arden
Role: Pinafore Actor
Justin Bohon
Role: Pinafore Actor
Justin Daniel
Role: Pinafore Actor
Michael Flanigan
Role: Pinafore Actor
John Hill
Role: Pinafore Actor
Will Reynolds
Role: Pinafore Actor
Michael Seelbach
Role: Pinafore Actor
Ryan Michael Shaw
Role: Pinafore Actor
Stephen Powell
Role: HMS Pinafore Singer
Henry Gummer
Role: Bonesman / Boatswain
Gregory Marcel
Role: Dancing Skeleton
Austin Williams
Role: Young Edward Wilson
Sophie Sutton
Role: Connie Wilson
Lars Gerhard
Role: Mr. Haupt
Tessa Kim
Role: Mr. Haupt's Translator
Peter Kybart
Role: Dr. Manheim
Rob Barnes
Role: Man at Jazz Club
Lee Bryant
Role: Mrs. John Russell, Sr.
Laila Robins
Role: Toddy Allen
Redman Maxfield
Role: Older Bonesman 1940
John C. Whitehead
Role: Reverend Collins
Jeff Skowron
Role: Deer Island Crooner 1940
Oleg Stefan
Role: Ulysses / Stas Siyanko
Meredith Deacon
Role: John Russell, Jr.'s Girlfriend
Josh Casaubon
Role: Army Man 1940
Christopher Evan Welch
Role: Photography Technical Officer
Tuc Watkins
Role: Sound Technical Officer
Leonard Logsdail
Role: Tailor
Eric Lindh
Role: Tailor Shop Guard
Trace Taylor
Role: Cryptographer
Amanda Barron
Role: Cryptographer
James Faulkner
Role: Lord Cooper
Robert Ian Mackenzie
Role: Cambridge Club Butler
Dieter Riesle
Role: Herr Franck
Sándor Técsy
Role: Sasha, Ulysses' Aide
Tommy Nelson
Role: Edward Wilson Jr. - Age 6-7
Greg Plitt
Role: Guard with Sullivan
Marcos Cohen
Role: Dr. Ibanez
Jeff Applegate
Role: Michael Johnson
Jon Monett
Role: CIA Insect Man
Sandee Conrad
Role: Edward's Secretary
Jonathan Dokuchitz
Role: Husband Dinner Guest
Susan Haskell
Role: Wife Dinner Guest
Sjoerd Dejong
Role: Santa Claus
Neal Huff
Role: Teletype Operations Officer
Jason Butler Harner
Role: Teletype Communications Officer
Amy Wright
Role: Safe House Operations Officer
Matthew Humphreys
Role: Cherry Orchard Actor
Karron Graves
Role: Cherry Orchard Actress
Robert C. Kirk
Role: Laura's Taxi Driver
Reathel Bean
Role: 'Dame' Bonesman
Jerry Coyle
Role: 'Dame' Bonesman
Wally Dunn
Role: 'Dame' Bonesman
Roger Rathburn
Role: 'Dame' Bonesman
Michael Melvoin
Role: Piano Player
Glenn Kalison
Role: Telephone Operations Officer
John Knox
Role: Technical Service Officer
Benjamin Eakeley
Role: Bonesman 1960
Gino Cafarelli
Role: Palmi's Bodyguard
Tommy DeVito
Role: Palmi's Bodyguard
Stefanie Nava
Role: Tina Palmi
Isabella Cimato
Role: Palmi's Granddaughter
Jimmy Marchese
Role: Palmi's Grandson
Robert Prescott
Role: Bonesman MC 1961
Bill McHugh
Role: Reverend Christiansen
Ann Hampton Callaway
Role: 1961 Deer Island Singer
Christopher Druckman
Role: FBI Agent
John Henry
Role: Philip Allen's Driver
Dave Payton
Role: College Student (uncredited)
Vladislav Kozlov
Role: Executioner (uncredited)