Reviewed by Maitland McDonagh

Robert De Niro's icy drama, from Eric Roth's densely researched original screenplay, unfolds over the course of two decades and traces the history of modern-day spycraft, finding in the moral destruction of one key player a sweeping indictment of the agency's poisonous culture of lying, manipulation, self-righteousness and paranoia.

The film opens in 1961 with Edward Wilson (Matt Damon), a high-level cog in the Cold War espionage machine, helping engineer the disastrous Bay of Pigs invasion. Designed to destabilize Fidel Castro's government, the botched operation instead embarrassed the Kennedy administration and forced the resignation of key senior CIA management. It's clear that the mission was deliberately undermined from within, and the traitor's identity may be connected to the blurry black-and-white photo of a nude couple and an accompanying audiotape that are slipped mysteriously under Wilson's door. The story then cuts back and forth between Wilson's efforts to identify the photo's subjects and origin and flashbacks to his rise through the ranks, which parallels the development of the organization itself.

1939: General Bill Sullivan (De Niro) is charged with creating an agency to gather intelligence, cultivate informants and help stage-manage events abroad with an eye to protecting American interests — "American" being synonymous with the values and concerns of wealthy, politically conservative white men of Anglo-Saxon origin. Wilson, a wealthy, socially-prominent Yale senior who wants to be a poet and has just been inducted into Skull and Bones, the secret society whose privileged members traditionally replenish the ranks of the patrician WASP establishment, is one of his early recruits. In short order Wilson betrays his mentor, Nazi-sympathizer Dr. Fredericks (Michael Gambon) and throws over his ordinary girlfriend for Margaret "Clover" Russell (Angelina Jolie), the volatile sister of a well-connected classmate. He's then posted to London, leaving his pregnant bride at home; their son is six by the time he returns. Wilson learns the ropes of skullduggery from supercilious British spy Arch Cummings (Billy Crudup), a Cambridge-educated child of privilege like himself, and none other than Dr. Fredericks — lesson one is that nothing is as it seems. Damon's subtle, painfully introverted performance is the film's linchpin, but the supporting cast — notably Gambon, Crudup, William Hurt, Alec Baldwin, Joe Pesci, John Turturro, Keir Dullea, Timothy Hutton and Gabriel Macht — is top notch. Roth's screenplay, steeped in the peculiar rituals, lock-jawed repression and smug sense of superiority of the WASP ruling class that both shaped America's intelligence community and made it vulnerable, is less interested in derring-do than back-room deals and the day-to-day drudgery of spying, driven by the notion that espionage is a cynical high-stakes game played with people's lives and the ante is human decency and connectedness.