The Good Shepherd is a bold, ambitious, but ultimately unsuccessful attempt at staging an American epic around a clan of WASPs who come of age in the late 1930s. This clan is not made up of cousins and other kinsmen, a la The Godfather, but brothers of privilege who first learn the value of keeping one's mouth shut during pee-on hazing rituals for Skull & Bones. The secret-handshake games these tight-knit young men practice at Yale will be put to the test when war against Germany leads to the hasty creation of a foreign intelligence service, and Uncle Sam comes looking for the best and the brightest -- "Jews, Catholics and Negroes need not apply." Luck graces one of the chosen few, Edward Wilson, (Matt Damon) when his college professor is discovered to be moonlighting as a covert Nazi organizer. Ousting the professor from the shadows brings Wilson to the attention of the right people, who put him on a track that will nurture his secretive side and eventually saddle him with the secrets of a nation.

Wilson is supposedly a composite of James Jesus Angleton and at least one other forefather of America's intelligence community, but factual bona fides are not a priority here. The film's energy isn't really devoted to exploring why and how the CIA came into being, but to solving surface-level mysteries about double agents -- there's even a running attempt to decipher the clues in a piece of audio/video, Mission Impossible-style. The large roster of characters includes a Kim Philby turncoat figure, played by Billy Crudup, who floats in and out of the piece seemingly at random. There's also Wilson's CIA handler, played by Robert De Niro, whose job involves looking solemnly at whoever he's talking to and saying things like "You won't be able to trust anyone," which in the movies usually translates to "I'm a spy." These characters and others in The Good Shepherd run up against an enormous time compression that's been unwisely forced on the picture. An original running time rumored to be well over three hours has been compacted down to something closer to half of that.

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Despite its flaws, there's a lot to admire about the film. The most successful element is Damon's spot-on performance as the zipper-lipped Wilson. Admirably sticking to the non-emotive essence of the character from beginning to end, Damon never draws on any actor's techniques to make Wilson seem more likeable or to hint at dimensions that should stay completely hidden. Like his earlier portrayal of Tom Ripley, Damon's Wilson is a smart man who's completely lacking in emotional intelligence. He operates solely by gaming people and making educated guesses about what they want to hear. He keeps his real identity bundled up as tight as his trenchcoat and doesn't enter into interpersonal situations that can't be controlled and managed from the outset. In one of the film's signature scenes -- one of the few truly effective scenes -- a clumsy attempt by Wilson at sexual intimacy with a strange woman has immediate, violent consequences. In his world, allowing oneself to be sexual at all is tantamount to being out of control. It's a risk that can't be taken.

The film's preoccupation with sexuality, and what it may or may not represent, could explain its most perplexing element: the presence of Angelina Jolie as Clover Wilson, wife of Edward. Jolie's exotic, un-WASPy beauty is only one of many question marks about her character; she exists almost completely outside the narrative, as an aggressively sexual, emotionally needy floozy who torments her husband simply by being so unlike him. Wilson is essentially shacking up with Jolie's character from Girl, Interrupted. Their marriage is inconceivable. In fact, Jolie's presence in the film smacks of studio intervention. By that I mean that she is one of the few actresses who can probably bag any part she wants within reason, overriding other considerations, like whether she's right for it. I would wager that was what happened in this case. The Good Shepherd's writer, Eric Roth, has even hinted around that he hoped to see the part offered to someone like Gwyneth Paltrow, who would have been a much more believable choice as a seen-but-not-heard 40s house-WASP.

Because neither Damon or Jolie are required to wear any significant age-makeup, the film grows increasingly bizarre as it advances through the years and the couple's twenty-something son (Eddie Redmayne) begins to play a major role in events, while looking exactly like a contemporary of his mom and pop. His increasing independence from his all-controlling father and his fleeting involvement in the intelligence game becomes a major sticking point and ends up drawing together many of the film's parallel concerns about loyalty, accountability and race. The latter subject comes into play when he decides to marry an African girl and bring such a visible outsider into the family home. You can imagine how that goes over with Wilson, who at one point in the film is asked by an Italian wiseguy what WASPs have left to call their own anymore. Wilson's answer: "The United States of America. The rest of you are just visiting." The Good Shepherd is a truncated American tragedy, noticeably half-finished and undercooked, but often tantalizing for the promise that clearly lay buried in the material, like unbroken codes.