Matt Damon as Edward Bell Wilson

Angelina Jolie as Margaret Ann Russell

Robert De Niro as Bill Sullivan

Alec Baldwin as Sam Murach

William Hurt as Philip Allen

Joe Pesci as Joseph Palmi

John Turturro as Raymond Brocco

Billy Crudup as Archibald Cummings

Tammy Blanchard as Laura

Michael Gambon as Dr. Fredericks

Timothy Hutton as Thomas Wilson

John Sessions as Valentin Mironov #1/Yuri Modin

Keir Dullea as Senator John Russell, Sr.

Martina Gedeck as Hanna Schiller

Gabriel Macht as John Russell, Jr.

Lee Pace as Richard Hayes

Eddie Redmayne as Edward Wilson Jr.

Mark Ivanir as Valentin Mironov #2

Yelena Shmulenson as Dollar Woman

Jack Martin as Dollar Little Boy

Anne-Marie Cusson as Philip Allen's Secretary

Robert Bermudez Cordell as Bay of Pigs Voiceover (voice)

David Crommett as Spanish Translator

Michael Arden as Pinafore Actor

Justin Bohon as Pinafore Actor

Justin Daniel as Pinafore Actor

Michael Flanigan as Pinafore Actor

John Hill as Pinafore Actor

Will Reynolds as Pinafore Actor

Michael Seelbach as Pinafore Actor

Ryan Michael Shaw as Pinafore Actor

Stephen Powell as HMS Pinafore Singer

Henry Gummer as Bonesman / Boatswain

Gregory Marcel as Dancing Skeleton

Austin Williams as Young Edward Wilson

Sophie Sutton as Connie Wilson

Lars Gerhard as Mr. Haupt

Tessa Kim as Mr. Haupt's Translator

Peter Kybart as Dr. Manheim

Rob Barnes as Man at Jazz Club

Lee Bryant as Mrs. John Russell, Sr.

Laila Robins as Toddy Allen

Redman Maxfield as Older Bonesman 1940

John C. Whitehead as Reverend Collins

Jeff Skowron as Deer Island Crooner 1940

Oleg Stefan as Ulysses / Stas Siyanko

Meredith Deacon as John Russell, Jr.'s Girlfriend

Josh Casaubon as Army Man 1940

Christopher Evan Welch as Photography Technical Officer

Tuc Watkins as Sound Technical Officer

Leonard Logsdail as Tailor

Eric Lindh as Tailor Shop Guard

Trace Taylor as Cryptographer

Amanda Barron as Cryptographer

James Faulkner as Lord Cooper

Robert Ian Mackenzie as Cambridge Club Butler

Dieter Riesle as Herr Franck

Sándor Técsy as Sasha, Ulysses' Aide

Tommy Nelson as Edward Wilson Jr. - Age 6-7

Greg Plitt as Guard with Sullivan

Marcos Cohen as Dr. Ibanez

Jeff Applegate as Michael Johnson

Jon Monett as CIA Insect Man

Sandee Conrad as Edward's Secretary

Jonathan Dokuchitz as Husband Dinner Guest

Susan Haskell as Wife Dinner Guest

Sjoerd Dejong as Santa Claus

Neal Huff as Teletype Operations Officer

Jason Butler Harner as Teletype Communications Officer

Amy Wright as Safe House Operations Officer

Matthew Humphreys as Cherry Orchard Actor

Karron Graves as Cherry Orchard Actress

Robert C. Kirk as Laura's Taxi Driver

Reathel Bean as 'Dame' Bonesman

Jerry Coyle as 'Dame' Bonesman

Wally Dunn as 'Dame' Bonesman

Roger Rathburn as 'Dame' Bonesman

Michael Melvoin as Piano Player

Glenn Kalison as Telephone Operations Officer

John Knox as Technical Service Officer

Benjamin Eakeley as Bonesman 1960

Gino Cafarelli as Palmi's Bodyguard

Tommy DeVito as Palmi's Bodyguard

Stefanie Nava as Tina Palmi

Isabella Cimato as Palmi's Granddaughter

Jimmy Marchese as Palmi's Grandson

Robert Prescott as Bonesman MC 1961

Bill McHugh as Reverend Christiansen

Ann Hampton Callaway as 1961 Deer Island Singer

Christopher Druckman as FBI Agent

Liya Kebede as Miriam

John Henry as Philip Allen's Driver

Josh Pence as Bonesman

Dave Payton as College Student (uncredited)

Vladislav Kozlov as Executioner (uncredited)