The year is 1949 and reporter Hugh Jameson is looking for a story. He focuses on Emma Porter, a woman who was accused of the axe murder of her father thirty seven years earlier. Jameson disappears during his search and his wife hires Charles Ripley P.I. to find him. Ripley's search leads him to Emma's son who has his own nasty secrets to protect.

Will Cole is a charismatic 35 year old paper mill laborer who seems to celebrate a life of bad choices. He lives and behaves as if he was still 18, womanizing and drinking and rejecting responsibility because he sees no reason to take life seriously. Surprisingly enough, despite his devil-may-care attitude, he has several important people in his life. He maintains a special relationship with Stan, an old mentor who lives in a nursing home, and Ruth, the only woman he truly cares about. Andrew is his best friend but grows tired of Will's antics, and he is soon to be married and moving on. Will constantly has something up his sleeve but his pranks inevitably bring pain and tragedy to those closest to him, forcing him to reevaluate his life and make some difficult decisions.