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Winesburg, Ohio begins with a prologue, describing an old writer who has hired a carpenter to rebuild his bed, so it will be level with his window. After the work is completed, the old writer lies in bed and thinks about death. As he nears sleep, all the people he has ever met pass slowly before his eyes. He sees them all as "grotesques," some amusing, some terribly sad, and some horrifying. Immediately after this experience, he climbs out of bed and writes everything that he saw down in a book, which he calls "The Book of the Grotesque." In this book, he conjectures that the world is full of different truths, all of them beautiful, but when a person seizes on and tries to live by only a single truth, that person's life becomes distorted. The old man writes on this subject for hundreds and hundreds of pages, his obsession almost making himself a grotesque; in the end, he never publishes the book.
After this peculiar introduction, the first chapter begins. Entitled "Hands," it tells the story of Wing Biddlebaum, an eccentric, nervous man who lives on the outskirts of the town of Winesburg, Ohio. Despite having lived in Winesburg for twenty years, Biddlebaum has never become close to anyone, with the exception of George Willard, a young man who works as a reporter for the Winesburg Eagle. On this particular evening, Biddlebaum is pacing on his porch, hoping that George will visit. As he paces, he fiddles with his hands, which are famous for their dexterity and wanton behavior. "Their restless activity," Anderson writes, "like unto the beating of the wings of an imprisoned bird, had given him his name." He has difficulty controlling his hands, which have a tendency to wander inappropriately of their own accord. The last time he was talking with George, he jerked back in horror after finding himself starting to caress the young man's face.
Biddlebaum's horror stems from his past as a schoolteacher in Pennsylvania, where he was named Adolph Myers. He was very talented, but during his passionate lectures, he would often caress the shoulders and heads of his pupils, and one boy accused him of molestation. The schoolteacher barely made it out of town with his life, changed his name, and moved to Winesburg, where he lives in a seclusion broken only by his friendship with George Willard. On this particular evening, George does not come to visit.
The next story, "Paper Pills," concerns the aged Doctor Reefy, who has worn the same suit of clothes for ten years. In the suit's deep pockets he keeps little scraps of paper, which eventually wad up into balls of paper. The old doctor was married once, to a much younger woman who died a year after their marriage. She was an heiress with two principal suitors, one who "talked continually of virginity," and one who said almost nothing at all before trying to kiss her. Eventually, she became pregnant by the quiet suitor, and went to Doctor Reefy for medical help. After she had a miscarriage, she and the doctor were married, and during their few months of happiness he would read to her from what he had written on the little scraps of paper in his pockets.
Winesburg, Ohio is an idiosyncratic work, falling somewhere between a novel and a collection of short stories. Its twenty-four sections all involve the inhabitants of Winesburg, and all are connected, though not directly linked as the chapters of a novel would be. The only framing device that Anderson provides for this succession of vignettes is the peculiar prologue entitled "The Book of the Grotesque," in which a nameless old man envisions caricaturized individuals obsessed with various truths. This vision provides a key to the rest of the work, since each one of the subsequent twenty-four sections can be interpreted as a portrayal of a "grotesque" human being. Anderson, however, does not make the connection explicit: he never confirms that the reader is reading the old man's "Book of the Grotesque," and even goes so far as to note that the "Book of the Grotesque" was never published.
Nevertheless, the connection between the old man's grotesques and the inhabitants of Winesburg is clear. Wing Biddlebaum, the first character introduced, bears an element of the grotesque in his odd relationship to his remarkable hands, which are the root of all his troubles. By means of flashback, it is revealed that his hands have stripped him of his teaching career and isolated him from the rest of humanity, even to the point of making him change his name. Through Biddlebaum's isolation and pitiable qualities, Anderson begins his exploration of the book's central themes: loneliness and alienation. Nearly all of his characters are alienated in some way, either physically or emotionally, from the rest of society. The major exception is George Willard, also introduced in the first section. George is the book's central character, with connections to several of the others, many of whom feel an urge to confide in him. He is also, in his youth and inexperience, one of the book's most uncomplicated figures. He does not bear the burdens that life has pressed on the backs of the other characters, and he feels no sense of alienation.