The Good Shepherd (2006)

Matt Damon plays upright young spy Edward Wilson in the globetrotting, decades-spanning, birth-of-the-CIA drama The Good Shepherd (2006). Over the course of thirty-five years in service to the government, Wilson witnesses the Cold War at its hottest and, more importantly, he causes skinternational incidents with the always-simmering Angelina Jolie and Martina Gedeck's left areola. Directed by Robert De Niro and produced by Francis Ford Coppola, The Good Shepherd is rife with eye-opening ladies who won't leave you counting sheep.