Cosmo Vitelli owns the Crazy Horse West, a strip joint in California. He's laconic, a Korean War vet, and a gambler. When we meet him, he's making his last payment on a gambling debt. Then, he promptly loses $23,000 playing poker at an illegal local casino. The guys he owes this time aren't so friendly, pressuring him for immediate payment. Then they suggest that he kill a Chinese bookie to wipe off the debt. Vitelli and the film move back and forth between the double-crossing, murderous insincerity of the gamblers and the friendships, sweetness, and even love among Vitelli, the dancers, a dancer's mother, and the club's singer, Mr. Sophistication.
Laconic and self-contained, Edward Wilson heads CIA covert operations during the Bay of Pigs. The agency suspects that Castro was tipped, so Wilson looks for the leak. As he investigates, he recalls, in a series of flashbacks, his father's death, student days at Yale (poetry; Skull and Bones), recruitment into the fledgling OSS, truncated affairs, a shotgun marriage, cutting his teeth on spy craft in London, distance from his son, the emergence of the Cold War, and relationships with agency, British, and Soviet counterparts. We watch his idealism give way to something else: disclosing the nature of that something else is at the heart of the film's narration as he closes in on the leak.
Cheyenne, a wealthy former rock star (Penn), now bored and jaded in his retirement embarks on a quest to find his father's persecutor, an ex-Nazi war criminal now hiding out in the U.S. Learning his father is close to death, he travels to New York in the hope of being reconciled with him during his final hours, only to arrive too late. Having been estranged for over 30 years, it is only now in death that he learns the true extent of his father's humiliation in Auschwitz at the hands of former SS Officer Aloise Lange - an event he is determined to avenge.