The filmmakers knew they needed someone to play Edward Wilson, whose performance would encapsulate the agent’s three-decade transformation from wide-eyed schoolboy to grim bureaucrat. 

Robinson describes Wilson as a man who must pay a high price for devoting his entire life to safeguarding democracy.  “He didn’t have a fun life.  He was always doing the right thing,” he feels.  According to the producer, the actor who would portray the central character needed to project a “quiet, smart, still-waters-run-deep type of person.  That’s who Matt Damon is.”

When approached for the project, Damon’s enthusiasm for the role was profound.  “Matt doesn’t make any compromises as far as his character,” commends De Niro.  “He’s not, all of a sudden, more sympathetic.” 

“He’s one of the finest actors working today,” adds Rosenthal.  “He’s willing to take on the challenge and is not afraid to push himself.” 

Damon’s likability was also crucial for a character whose actions don’t often elicit sympathy from the audience. 

“Matt is a really nice guy and that comes through, so you have an empathy for this character more than if you had another actor playing this part,” she notes.Damon was impressed with not only the screenplay; he was eager for the chance to work with De Niro. 

“It’s a masterful piece of writing, and as an actor, Bob’s the guy everyone worships,” he says. 

“To have him be there, you feel like you’re in good hands.”As part of his research, the Harvard-educated actor spent time with CIA veteran Bearden, visited several of the locations in which the story takes place and read multiple books on the CIA.  In order to better understand the impact that a career in the CIA would have on one’s home life, Damon also met some of the families of the men who founded the agency. 

“It’s hard for relationships to last; it’s a really high-pressure job,” relates Damon.  “Edward lives in a world where the stakes are high, and he can’t afford to trust even the people closest to him.” 

The main victim of this never-ending secrecy is Wilson’s wife, Margaret, his friend’s sister, whom the 22-year-old marries after a passionate encounter results in her pregnancy at Desert Island, a Skull and Bones retreat.Academy Award®-winning actor Angelina Jolie was cast to play this complicated character. 

With her exotic looks, the popular star might have initially seemed an unusual choice for the role of a debutante and senator’s daughter. 

But De Niro had no doubts that she could play an ingénue who would grow to live a life of constant uncertainty as a spy’s wife.  “Her instincts were great,” lauds De Niro. 

“She conveyed the things I thought were essential for Clover in the way she wanted to do it, in the way she was able to do it.”

As a young woman from a wealthy, conservative family, Clover has many personal obligations—from proper deportment to marrying within her social stratum.  Jolie found a spark within Clover with which she could identify. 

“There’s something about her that knows there is something wrong with it all,” reflects the actor. 

“She is kind of cheeky about it and a bit of a spitfire.  She has a wonderful sense of life.” But a shotgun marriage to a quiet man who does top-secret work proves to be Clover’s undoing. 

“She is affected by all the negative things about this world,” states Jolie.  “She is married to it, and a victim of being around nothing honest, being shut out as a woman…limited as a woman of this time.”

“Angelina has made more out of this than I could ever have imagined,” reflects screenwriter Roth.  “I think she’s spectacular.”Wilson’s work also profoundly influences his and Clover’s son, Edward Jr. 

Roth’s script had the six-year-old child first meet his father at the end of World War II, when Edward returns from Europe after the completion of his work for the OSS.  Played as a child by young actor AUSTIN WILLIAMS, Edward Jr. grows up in awe and fear of his emotionally remote, often physically absent father. 

To portray the role of the adult Edward Jr., De Niro and casting directors AMANDA MACKEY and CATHY SANDRICH GELFOND cast young British actor Eddie Redmayne while they were in London to cast two other British roles for the film. 

De Niro wanted to find an Edward Jr. that could embody a young man who was “fascinated, and at the same time repulsed, by what his father does.”

“Bob originally wanted to cast indigenously,” says Redmayne, who has won awards for his theater work in London’s West End. 

A stickler for authenticity, De Niro originally considered meeting only American actors for the role of Edward Jr. 

“Bob’s rigorous, and he worked me hard at it.”  However, after several readings with Damon and De Niro in New York, Redmayne proved he was perfect for the role.Redmayne also had the right look to play Edward and Clover’s son, a man who would follow in his father’s footsteps to get any semblance of attention from the senior Wilson. 

“He’s got something very classic about him that suits that period very well,” compliments Jolie.Another player who easily fit into the world of The Good Shepherd was Academy Award® winner William Hurt, cast in the role of CIA Director Philip Allen.  Born in Washington, D.C., Hurt lived all over the world during his childhood, due to the fact that his father was in the U.S. State Department. 

Hurt was hopeful that his participation in The Good Shepherd might help him understand another man. 

“My father came from a very powerful core of moral obligation to the idea of freedom in this country,” he says.  To fill the role of General Bill Sullivan—the U.S. Army official who helped create this country’s first intelligence service and who handpicks Wilson for a career in the CIA—Robinson, Rosenthal and De Niro came across the perfect actor: De Niro himself.General “Wild Bill” Donovan, the man upon whom the film’s General Sullivan was based, “got young men from Ivy League schools like Yale, who had more of an investment in their heritage and future,” says De Niro. 

“They would have more to lose if they didn’t win.” “Some actors have a certain commanding presence, and Bob kept describing who he was looking for.  He basically had to look in the mirror to find it,” notes Rosenthal.While the CIA was run by the U.S. elite, the agency’s staff included individuals from varying backgrounds, such as Wilson’s Italian-American assistant, Ray Brocco. 

To play the role of Wilson’s loyal right hand, De Niro cast acclaimed actor and graduate of the Yale School of Drama, John Turturro. 

Turturro had a small role in Raging Bull early in his career, and he has known the actor ever since.  In his research, Turturro came away with a strong sense of how Brocco’s work might affect his home life. 

“You can’t really talk about your work with your family,” he says.  “So you run the risk of disappearing from the lives of those you care about.”Another blue-collar character in Edward Wilson’s sphere of influence is Sam Murach, the FBI agent who approaches Wilson on the campus of Yale about a job with the government. 

Predating the CIA, the FBI’s ranks were unlike the privileged makeup of the CIA’s founders.  An FBI agent was more likened to a police officer, usually coming from a working-class background.

As with the roles of Clover and Brocco, De Niro knew exactly whom he wanted to play Murach: Alec Baldwin. 

Baldwin has recently appeared in several acclaimed independent films, garnered an Academy Award® nomination for his work in The Cooler and proved his versatility with comic roles on series from Will & Grace to 30 Rock. 

While the characters must obviously age over the decades that the story spans, Baldwin’s Murach undergoes a more extreme transformation in appearance than most, something that didn’t bother the theater-trained Baldwin.  “He’s been completely willing to jump in and do what he had to do for this role,” says Rosenthal. 

Another influential figure Wilson meets during his years at Yale is his English professor, Dr. Fredericks, played by Sir Michael Gambon.  For Gambon, best known to American audiences as the wizened Hogwarts headmaster, Dumbledore, in the recent Harry Potter films, the chance to work with De Niro was enough to convince him to take on the role of Fredericks. 

“To all us boys who are actors, he’s our god,” he laughs.  “They should get him to direct every film, then they could get any actor they wanted.”

Although born to privilege, Wilson feels somewhat of an outsider at Yale because of his hidden background.  Wilson’s father, played in a cameo role by Academy Award® winner Timothy Hutton, made choices that would cast his family under a cloud of suspicion. 

When Wilson joins the Skull and Bones, he must confess sins of his father to his new family, bonding him for life with them.To play Wilson’s classmates at Yale, the filmmakers cast a cadre of up-and-coming young actors such as GABRIEL MACHT, who plays Clover’s brother, John Russell. 

A golden boy with likable charm, Russell befriends Wilson and encourages him to join Skull and Bones.  Macht also bears a strong resemblance to Keir Dullea, seminal star of 2001:  A Space Odyssey, who plays John’s father, patrician Senator Russell.Another Bonesman in Wilson’s world is Richard Hayes, a young man who never warms to Wilson and serves as a constant thorn throughout his career. 

To play Hayes, the filmmakers cast Lee Pace, a Golden Globe nominee for his role in Showtime’s Soldier’s Girl.  To explore his role, Pace felt it important to research the Bonesmen who served in the OSS. 

“These are guys who had a free pass anywhere.  They could get into any circle,” he says.  “They had a reputation for being wild adventurers who could slum it and get away with that, and also travel with aristocracy in Romania or Berlin or London.”Called to serve his country with Hayes, Wilson travels to London, leaving his new wife at home to await the birth of their child.  Within the OSS, Wilson works with several other recent Yale graduates. 

“They were 21-25 when they started the OSS,” remarks Pace.  “They were kids.”  In the OSS, Wilson learns the fundamentals of intelligence from British spy Arch Cummings, a charming Cambridge-educated young man. 

For the role of Cummings, the filmmakers initially met with English actors, but ultimately decided to cast an American actor, Tony Award nominee Billy Crudup, who had recently starred on Broadway in The Pillowman and in the thriller Mission: Impossible III.  

De Niro and Rosenthal had produced the film Stage Beauty, in which Crudup had starred as a Brit, so they knew he could well play an Englishman.  “Billy came in and did a reading for us that blew us away,” says Rosenthal.  “It’s another energy when Arch comes into the scene, and Billy just does that brilliantly.”

“Arch is a British intelligence officer who is assigned to be the primary contact for Edward in London,” says Crudup of his character.  “British intelligence was already pretty well established, so my character serves as a mentor.”As with Turturro, what was particularly interesting to Crudup was how the script told the story of the CIA through personal relationships. 

“Within this enormous conflict that was World War II, and then the Cold War, people’s relationships became terribly contorted,” he suggests.  “And the way that they tried to understand themselves and understand each other and develop relationships became perverted.” 

When a Russian defector named Valentin presents himself to Wilson and offers invaluable information about the KGB, Wilson is instantly distrustful.  How can he know whether the defector is genuine, or a mole sent by the KGB? 

Even if Valentin supplies information that is verified, how can Wilson be sure that the Russians are not giving up a few secrets in order to trick the CIA into trusting Valentin?  On the other hand, Valentin could be the prize KGB source that makes his career.

To play the pivotal role, the filmmakers cast classically trained British actor John Sessions.  Sessions has long been popular in the U.K. for his comedic choices, including the original TV series Whose Line Is It Anyway? 

“I love him in this role, because you’re not sure about him and you want to believe him,” shares Rosenthal. Wilson is most curious to obtain information from Valentin about Stas Siyanko, or “Ulysses,” Wilson’s counterpart at the KGB. 

As head of counterintelligence, the CIA agent’s mission is to learn as much as possible about the enemy’s own intelligence officers, how they think and where each one of their vulnerabilities lies. 

To play the role of Stas, the filmmakers looked to Russia and cast Oleg Stefan, who has starred in over 30 films in the former Soviet Union before his recent immigration to the United States.

“In some ways they have more of a connection with each other than they do with their governments,” reflects the director.  “In their profession, they can identify with each other’s problems because they’re very similar, just on two different sides.”    

What would prove most identifiable was the common theme of suspicion that all these men found.  Through the fellow spies, lovers and everyone else he meets along his journey, Edward Wilson would all too painfully learn his biggest lesson: Trust no one.