Matt Damon plays Edward Wilson, a very serious young man still reeling from the death of his father (Timothy Hutton). Wilson attends Yale and is inducted into the famous “Skull & Bones” secret society. It is through a society function that he is introduced to General Bill Sullivan (De Niro), who is recruiting for a new intelligence agency to be known as the OSS (which eventually became the CIA). Wilson’s serious reputation makes him a natural for learning how to use intelligence and, more importantly, counterintelligence to benefit America’s interests in WWII.

As the years go by, Edward becomes one of the best agents in the operation, working behind the scenes on things like the Bay of Pigs invasion. During these Cold War incidents, he continually tries to get the upper hand over his KGB equivalent. This becomes harder to do as Cuba and Russia ally. The desire for information brings about the use of some more extreme measures by the organization, including interrogation of captives and even the occasional use of physical abuse. While there’s no doubt that Edward loves America, he nevertheless fails to seem content in his work. World politics grow cloudier, which makes it harder to decide what is patriotic and what is ethically questionable.

Contrasting with his work is Edward’s family life, which doesn’t get nearly the same attention as his job. After accidentally impregnating a young woman named Clover (Angelina Jolie), he does “the right thing” by marrying her, only to take a job overseas the next week. Not until he’s older does Edward forge a tenuous relationship with his son, who wants to follow his father’s footsteps by joining the agency.

Framing all of this is a subplot involving the receipt of some pictures and an audiotape that indicate an intelligence leak. Edward follows the clues trying to figure out where exactly the agency’s mission has been compromised.

The Good Shepherd is not a straightforward account of the CIA’s birth. The narrative jumps around in time, sometimes showing us Edward as a young man, sometimes showing him in the burgeoning days of his career, and other times showing him as a veteran agent influencing policy and realizing what he’s missed family-wise. The predictable approach would be to simply document the series of events that led to the formation of the CIA, followed by a depiction of their key milestones in their operation.

The way the movie does it is much more interesting. It puts a human face on the agency, which is a paradox, as CIA agents more or less thrive on their blankness and anonymity. Edward Wilson is the embodiment of that. No matter what he’s going through, you can’t read any emotion in his face unless you look deeply into his eyes. (Matt Damon gives a superb minimalist performance here.) Why does he want to join the agency? He talks a lot about patriotism, yet you never feel that love coming off him. His patriotism is more intellectual than emotional. This is the quality that makes him such a standout agent: he believes in American ideals, yet doesn’t have the emotional temperament to question the things that need to be done in the name of national security.

Nevertheless, there’s a lot of ambiguity in The Good Shepherd’s central character. Edward’s inability (or unwillingness) to reveal his feelings causes him to miss out on a lot. There’s a great scene where Clover confronts him about his absenteeism as a parent; in the one moment where he lets loose, Edward angrily informs her that the work he’s done has been intended to make the world a better place for their son. The movie – written by Eric Roth – continually asks: What is the personal cost of this line of work? How do you prioritize global issues with personal ones? The film also questions how the acts of disinformation and intelligence-gathering affect the personality of the one who performs them. I especially liked the way the film ends, with Edward struggling to find a balance between his duty to the agency and his duty to his family. What he does is disturbing, but it also clarifies him a great deal.

With a running time of nearly three hours, The Good Shepherd is one of those movies that lets you settle into its subject matter. The pace is slow without ever really feeling that way. De Niro isn’t afraid to let us soak up the details and the atmosphere of the story. By not rushing through it, the film allows us to get deeper into Edward’s morality as he navigates increasingly ambiguous waters. The ultimate point may be that an agency like the CIA absolutely depends on people like Edward Wilson – people who don’t draw attention to themselves, don’t fear committing to a decisive action, and don’t second guess themselves.

I will say that the movie has moments of being a little confusing. At times, you don’t really understand what’s going on in a scene until later scenes fill in the gaps. In the end, I was able to put all the pieces together, but I had to work for some of it. That shouldn’t be construed as a criticism, though. It’s nice to see a movie that assumes the audience is smart enough to figure it out.

In addition to Damon, Jolie, and DeNiro, actors such as Alec Baldwin (as an FBI agent), Joe Pesci (as a mafia connection) and William Hurt (as a senator) all turn in solid performances. The Good Shepherd uses its all-star cast wisely, pulling everyone together for a story that is ambitious and complex, but also seemingly honest about the machinations that go on in the hallways of the CIA and in the minds of those who work there.

( 1/2 out of four)

The Good Shepherd is rated R for violence, sexuality and language. The running time is 2 hours and 45 minutes.

To learn more about this film, check out AskMen.com: The Good Shepherd