Henry Lightcap is a fifty-three years old womanizing alcoholic with pancreatic cancer. He is heading to his birthplace in Stump Creek, Virginia to see his family one last time before he dies. Through his journey, Henry examines his past to figure out his own personality. Henry is not a bad person, and he cares deeply for those around him. However, Henry's history with women is bad, to say the least, and he has had a string of bad luck and made bad decisions that have resulted in a lifetime of misery. Henry's first wife, Myra, wanted him to become something he opposed. When he wouldn't, she left and was impregnated by another. Henry tried to step up and be a father to the baby, but in the end, he couldn't be boxed into a city. He left Myra and met Claire, with whom he falls in love. He courts her, marries her, and the two are blissfully happy. However, following her death, Henry returns to his drunken, wayward life. After meandering for years, healing, he meets Elaine and marries her. But soon, her own past times and his begin to clash, and he again finds love in other women and alcohol.