One Spry Spy: Damon’s CIA agent doesn’t age a day in 30 years.

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Even if it isn’t historically credible, the notion that the United States lost its innocence during World War II makes for a tidy film-noir storyline: Americans saw the horrors of Auschwitz and Bataan and became jaded and weary, only to realize that a new war had already begun. Robert De Niro’s The Good Shepherd covers several decades, and Steven Soderbergh’s The Good German transpires in a few days, but both turn on an American’s encounter with the infamy unloosed by the Second World War. And while the first film is a solemn epic and the second a black-hearted trifle, both flatter their protagonists—The Good Shepherd by supposing that its Edward Wilson is the equal of European rogues, The Good German by imagining that its Jake Geismer isn’t.

A circumspectly fictionalized account of how the OSS became the CIA, The Good Shepherd is a tale of secrets, codes of silence, and malevolent male bonding. Screenwriter Eric Roth, whose credits include Munich and The Insider, has half-jokingly called the film a WASP equivalent of The Godfather. The opening image is a snippet of surveillance video documenting a hotel-room tryst, but that quickly yields to buttoned-down Arlington, where Edward Wilson (Matt Damon) is easing a collapsed ship model into a bottle. Distractingly, the movie’s central character has been given a name that’s very close to that of Edwin Wilson, the former CIA agent who in 1983 was found guilty of selling explosives to Libya (a conviction ultimately overturned). The actual prototype of Damon’s Wilson, however, is James Jesús Angleton, the notoriously paranoid spymaster whose hobbies were orchids and fly fishing rather than model ships.

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Like Angleton before him, Edward Wilson attends Yale and develops an interest in poetry. Backstage at a student performance in which he’s performed in drag, Edward is asked to join Skull and Bones, the secret society that’s produced many spies and politicians. He falls in love with a deaf student, Laura (Tammy Blanchard), yet ends up marrying Margaret “Clover” Russell (Angelina Jolie), who throws herself at him at a Skull and Bones retreat. Though Clover is pregnant at the wedding, the groom doesn’t meet his son until the boy is 6. Edward has been recruited by the OSS and is off to Europe, where he’ll learn deceit, betrayal, and other skills of the counterintelligence officer.

The story’s spine is a few weeks in 1961, during which the tight-lipped Edward helps plan the failed Bay of Pigs invasion of Cuba and comes to suspect that a mole betrayed the operation. But the narrative returns to Yale before World War II and advances to Edward’s dealings with the double agent who exposes an urbane British spy (Billy Crudup) apparently modeled on Kim Philby. There are also various asides about the strained condition of Edward’s marriage, and a subplot involving his namesake son (Eddie Redmayne), who grows up to be a CIA agent whose imminent marriage provides one of several major developments as The Good Shepherd picks up the pace in the last 20 minutes of its nearly three-hour running time. By then, most of the usual suspects—Alec Baldwin, William Hurt, John Turturro, Michael Gambon, Timothy Hutton, and De Niro himself—have played a scene or two, without stealing the spotlight from the star for more than a moment. Damon even gets to upstage Joe Pesci in one of the rare scenes in which Edward turns openly nasty. (Conceptually, it’s a reprise of the actor’s lecture to the Arab prince in Syriana.)

Only the second film directed by De Niro, who made A Bronx Tale 13 years ago, The Good Shepherd is sober and assured, with impeccable cinematography by Robert Richardson. Yet the events are so cryptic that the movie should probably come with a study guide, and the director makes some odd choices. He barely ages Damon, who looks incongruously boyish as a middle-aged man; this unchanging appearance magnifies the perplexity caused by the many flashbacks and flash-forwards. Most curiously, De Niro and Roth treat family life as the crux of the story. Absorbed by his globe-trotting work, Edward certainly isn’t an ideal husband and father, but then his marriage—accomplished with the patrician equivalent of a shotgun—was shaky from the start. The attention paid to Clover’s unhappiness justifies the casting of Jolie in what is essentially a bit part, but it doesn’t fit with the script’s emphasis on the craft of espionage. Edward’s father’s suicide is the dark secret he reveals at his Skull and Bones initiation, and the subject resurfaces in the movie’s final scene. That motif would suggest that The Good Shepherd is deeply concerned with its hero’s psychology, but it sure isn’t. Edward personifies an entire nation that can’t return to isolationism, and his home life is just a diversion from a film that says both too much and not enough about how the United States became a global fixer.