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

Oleg Stefan

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)