Considered one of the earliest works of modernism, this collection of short stories is structured around the childhood and adolescence of protagonist George Willard who grows up in the small Ohio town of Winesburg. Loosely based on Anderson’s own childhood in Clyde, Ohio, George wants to be a writer, and to that end writes for the town’s newspaper office, whose mission is to include as many names of locals in each issue. The final story of the collection sees George leave Winesburg for the big city.
Each story follows a different character, and over the course of the collection a sense of the town’s character as well as the changes it undergoes over time emerges, as it takes place during a period characterized by “a sudden and almost universal turning from the old handicrafts towards our modern life of machines.” While there is a certain romanticism present in many of these stories—or rather, romance, with so many stories following couples in the dark—there is also a certain frankness to these romances, as young men and women both succumb to physical desire, with few long-term ramifications other than emotional confusion and yearning. Several men experience homoerotic desire, desire which is shunned and marked as wrong by the larger community, but the very presentation of such desire is quite startling in a text from 1919.
The collection is characterized as a collection of “grotesques,” and opens with a story of an old writer who leaves his bead in order to capture a sense of the parade of figures he seems to be haunted with in his old age, figure of all of the people he had ever known who in his head had become grotesques: “The grotesques were not all horrible. Some were amusing, some almost beautiful, and one, a woman all drawn out of shape, hurt the old man by her grotesqueness.” Claiming to have read this unpublished collection of grotesques and have it “made an indelible impression on my mind,” the author then proceeds to write such a collection. The word “grotesque” here highlights the very selective and stylized nature not only of Anderson’s own writing, but of the nature of writing in general. In keeping with the larger themes which would become so important in the works of high modernism, in which authors experimented with forms in an attempt to make a real connection, to more fully convey a human experience, Anderson early on identifies the difficulty (and potential futility) in any such attempt. By rejecting any larger theme of plot or narrative for instead this collection of stories and characterizations, Anderson creates a very real and believable community.