Winesburg, Ohio, Sherwood Anderson's most famous book, is a peculiar work, part novel and part collection of short stories. Its twenty-four sections are interconnected accounts that focus on various inhabitants of Winesburg, a sleepy midwestern town, around the turn of the century. The book opens with a framing device of sorts: the prologue-like section entitled "The Book of the Grotesque," in which a nameless old writer has a bedtime vision of human beings who pursue various "truths" to so great an extent that they become "grotesque." These hallucinations prefigure the lives of the inhabitants of Winesburg (at least of those inhabitants in whose lives the reader is allowed to peer). From the would-be Old Testament patriarch Jesse Bentley, to the filthy, obese, misogynistic Wash Williams, the souls of Anderson's Winesburgers are all somehow deformed.
Most of these deformations spring from two linked sources--alienation and loneliness. Some of Anderson's characters are completely cut off from human contact, like Wing Biddlebaum, an ex-teacher in hiding after being accused of molesting a student, or Enoch Robinson, who fills his New York apartment with imaginary friends. Others, especially women, are simply starved for love, like Alice Hindman, jilted by her only lover, or Elizabeth Willard and Louise Bentley, both stuck in loveless marriages. Indeed, the unhappiness of married life is a persistent theme in the book. Again and again, characters reach out to other people, hoping to quell their loneliness through love or companionship, and again and again, they are disappointed. Happiness is a rare commodity in Winesburg, grasped only by a few, like the ever-ebullient Joe Welling or the cheerful Tom Foster, who can appreciate better than anyone else the simple pleasures of life.
The picture is largely bleak for the other characters. Like Theodore Dreiser and Emile Zola, Anderson was a master of literary naturalism, offering a harsh and pessimistic assessment of the human condition. But while Dreiser and Zola situated their unhappy characters amid the brutality of industrial cities and mining towns, Anderson finds unhappiness, alienation and despair in what one might suppose a gentler, more innocent place--the rural, picturesque setting of a typical, American, small town. The existence of social norms, however, constrains the town's inhabitants, and public opinion proves a powerful force in shaping individuals.
The overall structure of the book is determined by the development of George Willard, the newspaper reporter and budding writer who crops up repeatedly, appearing in fifteen of the twenty-four stories. Anderson allows us to track his development from a callow youth who has foolish fancies, sexual adventures, and near-epiphanies, to the edge of adulthood. His journey takes place in the background for much of the book: he is the person to whom the other Winesburgers pour out their hearts, and in many stories he is only there as a listener, a filter between his fellow townsfolk and the reader. In the closing stories, though, after his mother's death, he steps forward into manhood and prepares to leave Winesburg for the wider world. When, in the last story of the novel, George takes the train away from Winesburg, the reader goes with him, leaving behind the grotesques to their futile search for love and happiness in a small and unfeeling world.