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

Jeff Skowron

Deer Island Crooner 1940

Oleg Stefan

Ulysses / Stas Siyanko

Олег Штефанко

Josh Casaubon

Army Man 1940

Christopher Evan Welch

Photography Technical Officer

Tuc Watkins

Sound Technical Officer

Amanda Barron

Cryptographer

James Faulkner

Lord Cooper

Robert Ian Mackenzie

Cambridge Club Butler

Dieter Riesle

Herr Franck

Tommy Nelson

Edward Wilson Jr. - Age 6-7

Greg Plitt

Guard with Sullivan

Jonathan Dokuchitz

Husband Dinner Guest

Neal Huff

Teletype Operations Officer

Jason Butler Harner

Teletype Communications Officer

Amy Wright

Safe House Operations Officer

Matthew Humphreys

Cherry Orchard Actor

Robert C. Kirk

Laura's Taxi Driver

Reathel Bean

'Dame' Bonesman

Wally Dunn

'Dame' Bonesman

Glenn Kalison

Telephone Operations Officer

Gino Cafarelli

Palmi's Bodyguard

Robert Prescott

Bonesman MC 1961

Bill McHugh

Reverend Christiansen

Liya Kebede

Miriam

Josh Pence

Bonesman

Nyasha Hatendi

Thomas Lumumba (uncredited)