Winesburg, Ohio has the most memorable cast of characters in 20th-century fiction. Listeners will remember at least a few stories and their characters for the rest of their lives. Each of the 23 stories stands on its own. Each is also interwoven into the fabric of the book. Winesburg has a special glow, a grace, poignant feelings, and a magical quality. Winesburg moves forward in a cascading fashion to the final chapters with Helen White, the most beautiful and richest girl in Winesburg, and "Departure" with George Willard, the charismatic character instrumental to all the characters, who reveal themselves through conversation - or a lack of it - with George.
The primary characters in some stories become the bit characters in others, much as Tom Stoppard showed that Hamlet was only a bit character in the lives of the hangers on, Rosencrantz and Guildenstern. Winesburg avoids isms, making it a purely literary work. The only political comments involve characters talking to each other, not pushing political views. Winesburg is not narrowly realistic as in Dreiser's novels. Rather, Winesburg is broadly realistic, because it involves everything good and bad about people and their circumstances.
At first it seems that everyone is stuck in Winesburg. But as you listen, you will notice that most people have been elsewhere or are on a road from or to some other place, either physically or in dreams. The town is vibrant with the "moving on" of American life, both in the character's thinking and doing. For all of these reasons, these characters seem far more timeless than those of more famous 20th-century authors, such as Hemingway, Fitzgerald, Dreiser, Lewis, or Faulkner. Those authors recognized this at some level and, with the exception of Fitzgerald, acknowledged that Anderson was the master from whom they learned. Jack Kerouac may have said it best: "Winesburg sticks to your ribs."