In the winter of 1974, a time of great political unrest, Samuel J. Bicke (Sean Penn) is a forty-four-year-old man who wants to believe in something – anything. But at every turn, his faith -- in himself and in the world around him -- is undermined. He is separated from his wife, Marie (Naomi Watts), who refuses to consider the reconciliation he wants so desperately. He is estranged from his brother Julius (Michael Wincott), a businessman whose success mocks Bicke’s constant string of professional failures. And, with his personal life in such disarray, he is also struggling to hold onto yet another job for which he is fundamentally unfit. An idealist who detests lying in any form, Bicke is miserable working as a salesman in an office supply company, a position that routinely requires him to be insincere, opportunistic, and deceitful.
The only bright spot in Bicke’s life is his dream of opening a door-to-door tire repair service with his auto mechanic friend, Bonny (Don Cheadle). Their business proposal requires a modest bank loan. Bicke applies and nervously waits the requisite period for the loan application to be processed. He is on edge the whole time because the outcome -- his only chance at a meaningful future -- is so important to him. As his anxiety mounts, Bicke begins to fall apart, and in his vulnerable state, sees injustice and hypocrisy everywhere. He thinks it is wrong that Marie, who works at a bar to support their three children, has to wear short skirts to get bigger tips. Or, that Bonny’s customers at the garage get away with being abusive just because he is black.
Bicke would like to strike out at all the offenders, but there are too many dragons to slay. However, there is one villain who looms large. For Bicke, Richard Nixon, described by Bicke’s boss (Jack Thompson) as the greatest salesman in history because he swindled the American people twice, becomes the embodiment of everything that is wrong with the world.
When Bicke experiences a series of ill-fated events -- his loan is rejected, his ex-wife and his brother abandon him, and his dreams of starting his own business die unrealized -- he decides the only way to reclaim his insignificant life is to carry out a grand, historic gesture that will make his presence felt. At this point, dreams give way to delusions. A new Samuel Bicke, uncharacteristically resolute and resourceful, sets out on a chilling crusade to right the world’s wrongs. He has an appointment with history.