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When I was putting together the list of books for the Tournament of Novels, I kept stumbling across titles that I had seen before, but had never considered reading. Shamed by my sense of having missed out on so much great literature, I started adding these novels to my reading list. The first one that I recently completed was Sherwood Anderson’s Winesburg, Ohio .

The list of writers whose style was influenced by Anderson includes William Faulkner, Ernest Hemingway, Virginia Wolfe, and John Steinbeck. Reading his novel it is easy to see the resemblance of the students on the teacher. But it is also difficult to imagine why Winesburg, Ohio is considered a great novel.

That fact that the loose collection of stories is considered a novel at all is a bit of stretch. As the literary critic Malcolm Lowry notes in the introduction to the version I read, Anderson “never even wrote a book in the strict sense of the word. A book should have a structure and development, whereas for Anderson there was chiefly the flash of lightening that revealed a life without changing it.”

The fictional town at the center of the novel is populated by characters Anderson called “grotesques.” The term is fitting since almost all the characters are odd, ugly, or bizarre. What they are not is believable. Each of them has a desire to express a something within them that they consider inexpressible. But almost without exception, they come across as the types of small town residents that could only exist in the mind of a student getting their MFA in creative writing. There is something missing that prevents them from being real.

To understand what is lacking, it is useful to compare Anderson to another writer who focused on the grotesque—Flannery O’Connor. As Robin Darling Young wrote in the March 2000 issue of First Things :

Flannery O’Connor used her best instruments, insight and poetic expression, to force her characters right up to the edge of the artistic abyss. On the edge of the cliff, gesturing exaggeratedly to us, they are just one degree away from caricatures, often uttering words just this side of ridiculous, comic in their tragic devices and desires. They stalk their way through this visible world while the invisible one, the realm of grace, bears down on them with a mercy that often leaves them mortally wounded.

Anderson’s grotesques do not feel the weight of grace or mercy. At most, they feel an existential angst that originates solely from within themselves—or, more accurately, from within Anderson. The world of Winesburg, Ohio seems less than real because it exists in an imagined universe in which the only reality is the visible world.

As Lowry notes, all of his famous disciples—and most of his readers—had abandoned Anderson by the 1930s. If Winesburg, Ohio —his masterwork—is any indication, they were justified in moving on. But what explains the inclusion of the book on so many lists of great novels?

Long ago I realized not to trust my own literary instincts. (As a reader I’m a bit of a Victorian, preferring a plot, a coherent narrative, believable characters, etc. I have a bias against word games that are passed off as novels (e.g., most postmodern works) and literary novels filled with characters so dull that if you met them in real life you’d do whatever it took to avoid interacting with them.) I may be missing something profound in Anderson’s book. There must be, after all, a reason that the board of the Modern Library included it on their list of 100 Best Novels . So before making a final judgment I’ll ask the readers of First Things , a group that includes some of the most literarily savvy folks I know, to weigh in on the matter.

If you’ve read Winesburg, Ohio —or any of Anderson’s other works—let’s hear what you think. Am I completely off base? What is the reason this book is considered worthy of such esteem?

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