| Directed by | |
|---|---|
 | Robert De Niro |
| Starring | ||
|---|---|---|
 | Matt Damon | Edward Wilson |
 | Angelina Jolie | Margaret 'Clover' Russell |
 | Alec Baldwin | Sam Murach |
| Tammy Blanchard | Laura |
| Billy Crudup | Arch Cummings |
| Robert De Niro | Bill Sullivan |
| Keir Dullea | Senator John Russell, Sr. |
 | Michael Gambon | Dr. Fredericks |
| Martina Gedeck | Hanna Schiller |
| William Hurt | Philip Allen |
| Timothy Hutton | Thomas Wilson |
| Mark Ivanir | Valentin Mironov #2 |
| Gabriel Macht | John Russell, Jr. |
 | Lee Pace | Richard Hayes |
 | Joe Pesci | Joseph Palmi |
 | Eddie Redmayne | Edward Wilson Jr. |
| John Sessions | Valentin Mironov #1 / Yuri Modin |
| Oleg Shtefanko | |
 | John Turturro | Ray Brocco |
| Yelena Shmulenson | Dollar Woman |
| Jack Martin | Dollar Little Boy |
| Anne-Marie Cusson | Philip Allen's Secretary |
| Robert Bermudez Cordell | Bay of Pigs Voiceover |
| 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 Keimes | |
| 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 Whitehead | |
| Jeff Skowron | Deer Island Crooner 1940 |
| 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 |
| Sndor Tcsy | |
| Tommy Nelson | Edward, 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 |
| Will Blomker | Skull and Bones Member |
| Carl Burrows | Professor |
| Laura Butler | Extra |
| Frank Cadillac | Counterman |
| Pete Carmen | Teletype Communications Officer |
| Cuyle Carvin | Suicide Victim |
| Fidel Castro | Self |
| Dominick Cicco | Protestor |
| Scot Cregan | CIA Agent |
| Ed Cuffe | Edward's Uncle |
| Robert Dearle | War Office Worker |
| Yevgeniy Dekhtyar | Russian Agent |
| Brandon deSpain | Russian Soldier |
| Todd Detwiler | CIA Agent |
| Jonah Falcon | Waiter |
| John Farrer | Bonesman |
| Roy William Gardner | Ed's Bonesman |
| Turi Haim | Theatre Patron |
| Darryl Reuben Hall | Black Bar Patron |
| Nyasha Hatendi | Thomas Lumumba |
| Adolf Hitler | Self |
| Katherine Hoskins Mackey | Mom |
| Hristo Hristov | Guard |
| John F. Kennedy | Self |
| Vladislav Kozlov | |
| Aaron Michael Lacey | CIA Agent |
| Orest Ludwig | Room Service Man |
| Josh Pence | Bonesman |
| Nick Poltoranin | Russian Soldier |
| Mark Pomirtchi | Extra |
| Justin Restivo | Yale Student |
| James Lloyd Reynolds | Field Officer |
| Drew Seltzer | Edward's Classmate |
| Reyna Shaskan | Voice |
| Diana Shneider | Irina Russell |
| Leonard Silver | Civil Servant |
| Christopher Stadulis | Under Cover CIA Agent |
| Rick Voight | Mr. Robbins |
| Alec Von Bargen | Fidel Castro |
| John Wernke | Bonesman #3 |
| Frank C. Williams | Butler |
| Jeremy Woods | Theatre Audience Member |
| Jonah Young | |
| Danny Zaccagnino | Bonesmen |
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