Matt Damon
Edward Bell Wilson

Angelina Jolie
Margaret Ann Russell

Robert De Niro
Bill Sullivan

Alec Baldwin
Sam Murach

William Hurt
Philip Allen

Joe Pesci
Joseph Palmi

John Turturro
Raymond Brocco

Billy Crudup
Archibald Cummings

Tammy Blanchard
Laura

Michael Gambon
Dr. Fredericks

Timothy Hutton
Thomas Wilson

John Sessions
Valentin Mironov #1/Yuri Modin

Keir Dullea
Senator John Russell, Sr.

Martina Gedeck
Hanna Schiller

Gabriel Macht
John Russell, Jr.

Lee Pace
Richard Hayes

Eddie Redmayne
Edward Wilson Jr.

Mark Ivanir
Valentin Mironov #2

Yelena Shmulenson
Dollar Woman

Jack Martin
Dollar Little Boy

Anne-Marie Cusson
Philip Allen's Secretary

Robert Bermudez Cordell
Bay of Pigs Voiceover (voice)

David Crommett
Spanish Translator

Michael Arden
Pinafore Actor

Justin Bohon
Pinafore Actor

Justin Daniel
Pinafore Actor

Michael Flanigan
Pinafore Actor

John Hill
Pinafore Actor

Will Reynolds
Pinafore Actor

Michael Seelbach
Pinafore Actor

Ryan Michael Shaw
Pinafore Actor

Stephen Powell
HMS Pinafore Singer

Henry Gummer
Bonesman / Boatswain

Gregory Marcel
Dancing Skeleton

Austin Williams
Young Edward Wilson

Sophie Sutton
Connie Wilson

Lars Gerhard
Mr. Haupt

Tessa Kim
Mr. Haupt's Translator

Peter Kybart
Dr. Manheim

Rob Barnes
Man at Jazz Club

Lee Bryant
Mrs. John Russell, Sr.

Laila Robins
Toddy Allen

Redman Maxfield
Older Bonesman 1940

John C. Whitehead
Reverend Collins

Jeff Skowron
Deer Island Crooner 1940

Олег Штефанко
Ulysses / Stas Siyanko

Meredith Deacon
John Russell, Jr.'s Girlfriend

Josh Casaubon
Army Man 1940

Christopher Evan Welch
Photography Technical Officer

Tuc Watkins
Sound Technical Officer

Leonard Logsdail
Tailor

Eric Lindh
Tailor Shop Guard

Trace Taylor
Cryptographer

Amanda Barron
Cryptographer

James Faulkner
Lord Cooper

Robert Ian Mackenzie
Cambridge Club Butler

Dieter Riesle
Herr Franck

Sándor Técsy
Sasha, Ulysses' Aide

Tommy Nelson
Edward Wilson Jr. - Age 6-7

Greg Plitt
Guard with Sullivan

Marcos Cohen
Dr. Ibanez

Jeff Applegate
Michael Johnson

Jon Monett
CIA Insect Man

Sandee Conrad
Edward's Secretary

Jonathan Dokuchitz
Husband Dinner Guest

Susan Haskell
Wife Dinner Guest

Sjoerd Dejong
Santa Claus

Neal Huff
Teletype Operations Officer

Jason Butler Harner
Teletype Communications Officer

Amy Wright
Safe House Operations Officer

Matthew Humphreys
Cherry Orchard Actor

Karron Graves
Cherry Orchard Actress

Robert C. Kirk
Laura's Taxi Driver

Reathel Bean
'Dame' Bonesman

Jerry Coyle
'Dame' Bonesman

Wally Dunn
'Dame' Bonesman

Roger Rathburn
'Dame' Bonesman

Michael Melvoin
Piano Player

Glenn Kalison
Telephone Operations Officer

John Knox
Technical Service Officer

Benjamin Eakeley
Bonesman 1960

Gino Cafarelli
Palmi's Bodyguard

Tommy DeVito
Palmi's Bodyguard

Stefanie Nava
Tina Palmi

Isabella Cimato
Palmi's Granddaughter

Jimmy Marchese
Palmi's Grandson

Robert Prescott
Bonesman MC 1961

Bill McHugh
Reverend Christiansen

Ann Hampton Callaway
1961 Deer Island Singer

Christopher Druckman
FBI Agent

Liya Kebede
Miriam

John Henry
Philip Allen's Driver

Josh Pence
Bonesman

Dave Payton
College Student (uncredited)

Vladislav Kozlov
Executioner (uncredited)

Nyasha Hatendi
Thomas Lumumba (uncredited)

Diana Shneider
Irina Russell (uncredited)

Alec Von Bargen
Fidel Castro (uncredited)

Rick Voight
Mr. Robbins (uncredited)