In The Good Shepherd, a tense Yalie named Edward Wilson (Matt Damon) is tapped to join Skull and Bones on the basis of his WASP bona fides. (The secret society politely overlooks his father's disreputable death.) He's uptight and pale and has a penchant for poetry, so you'd think the sexually charged initiation would send him for a loop. Instead, the ceremony—garden-variety mud wrestling, with some urination and public confessions thrown in for good measure—is rendered with a minimum of mystery and fear. Edward gets upset and storms out, then calms down and storms back in.

Recruited to join the fledgling CIA, Edward soon gets molested by a heaving girl named Clover (Angelina Jolie, so intent on being sexy that she has no chance to act). Inevitably, Clover gets knocked up, and Edward is pulled off a beach—where he's wooing his true love, a docile deaf girl—and forced to marry her. His job keeps him abroad for five years, so they never fall in love. (Tragic, I'm sure.) They do, however, beget a boy (Eddie Redmayne) with tight translucent skin and a distinctly froggy physiognomy.

As imagined by director Robert De Niro, Edward's covert CIA activities consist of a series of passwords and trapdoors and secret underground intelligence lairs, interspersed with flash-forwards in which he stalks the crucial leak that spoiled his pet project, the invasion of the Bay of Pigs. There's a sequence of ludicrous technological refinements on skimpy evidence. There's a password involving an elaborate order for hand-tailored suits. There's a torture scene in which a suspected Russian spy charges out the window after being fed an experimental truth serum called LSD. But thanks to flat dialogue by Eric Roth, a studiously internal performance by Matt Damon, and a palette consisting largely of murky beige, it's impossible to get invested in the film. I'm all for learning about the birth of the modern nation, but this spurious history class will put you straight to sleep.