The work is structured around the life of protagonist George Willard, from the time he was a child to his growing independence and ultimate abandonment of Winesburg as a young man.

Stylistically, because of its emphasis on the psychological insights of characters over plot, and plainspoken prose, Winesburg, Ohio is known as one of the earliest works of Modernist literature.

[10] Aside from its structural unity, the common setting, characters, symbolism and "consistency of mood"[11] are all additional qualities that tie the stories together despite their initial publication as separate tales.

Promoted to younger writers by Anderson himself,[12] Winesburg, Ohio has served as a representative early example of the modern short story cycle in American letters.

[13] Comparisons between Winesburg, Ohio and Jean Toomer's Cane (1923), Ernest Hemingway's In Our Time (1925), William Faulkner's Go Down, Moses (1942), and several of John Steinbeck's works, among others, demonstrate the pervasiveness of the formal innovations made in Anderson's book.

[12][14][15] The focus on George Willard's development as a young man and a writer has also led some critics to put Winesburg, Ohio within the tradition of "the American boy book, the Bildungsroman,[16] and the Künstlerroman".

"[31] Gertrude Stein, whose work Anderson was introduced to by either his brother Karl[32][33] or photographer Alfred Stieglitz[34] between 1912 and 1915, is also said to have played a key role in helping shape the unique style found in the stories.

Through his interaction (at first satirizing it before ultimately accepting it as essential to his development) with Stein's Three Lives (1909) and Tender Buttons (1914), Anderson found the plain, unambiguous voice that became a staple of his prose.

[36] Literary critic Irving Howe summarized the pair's connection aptly when he wrote, "Stein was the best kind of influence: she did not bend Anderson to her style, she liberated him for his own.

The influence of Theodore Dreiser and the Russians (Chekhov, Dostoevsky, and Tolstoy) were discounted by the author, the former for stylistic reasons,[37][38] the latter because he had apparently not read them prior to writing his book.

[54] This dynamic is present, in some form, in practically all of the stories, three fairly representative examples being the merchant's son, Elmer Cowley, in the story "Queer,” George's mother, Elizabeth Willard, in the stories "Mother" and "Death,” and Jessie Bentley in "Godliness.” In the former, the young man Elmer Cowley, incited by an imagined slight ("He thought that the boy who passed and repassed Cowley & Son's store ... must be thinking of him and perhaps laughing at him"[55] when in reality, "[George] had long been wanting to make friends with the young merchant...")[56] tries twice to tell George off but is unable to communicate his feelings either time, finally physically assaulting the young reporter.

[63][64] Barry D. Bort writes, "Criticism of Winesburg, Ohio has recognized this desperate need to communicate, but what has not been understood about Anderson's work is that this continual frustration serves as the context out of which arise a few luminous moments of understanding...

[64] Though rarely does escape come in the narrative present, many of the stories prominently feature anecdotes of past adventures where lonely and reserved characters run naked through the town on a rainy night (Alice Hindman in "Adventure"), drive their wagon headlong into a speeding locomotive (Windpeter Winters in "The Untold Lie"), and have window-shattering religious epiphanies (Reverend Curtis Hartman in "The Strength of God").

[note 2] Throughout the book, he plays the dual role of listener and recorder of other people's stories and advice,[65][66] and the young representative of the town's hopes[67] whose coming-of-age reaches its dénouement in the final tale, "Departure,” when George leaves Winesburg for the city.

At last, however, George begins to perceive that there is something more to be communicated between men and women than physical encounter..."[68] Yet this lesson is not solidified for the young reporter when, after boasting in a bar in the story "An Awakening,” he has a surge of "masculine power" and tries to seduce Belle Carpenter, only to be repelled and humiliated by her beau, the large-fisted bartender, Ed Handby.

[71] It is in the time they spend together that readers see "his acceptance of Helen as a spiritual mediator..." which signifies that "...George's masculinity is balanced by the feminine qualities of tenderness and gentleness, an integration that Anderson suggests is necessary for the artist.

"[72] The style of Winesburg, Ohio has often been placed at various points in the spectrum between the naturalism of Anderson's literary predecessor, William Dean Howells (who died almost one year after the publication of the book), contemporaries Theodore Dreiser and Sinclair Lewis, and the Modernist writers of the Lost Generation.

[85] Wing Biddlebaum and Dr. Reefy are just two examples of how throughout Winesburg, Ohio, Anderson builds myriad themes by adding symbolic significance to gestures,[86] weather conditions and time of day,[87] and events,[88] among other features of the stories.

"[25] Indeed, it is this de-emphasis of traditional story elements in lieu of experimentation with language that provides both a link and a rift between Winesburg, Ohio and the novels of the following decades;[89] whereas the simple, stripped-down vernacular that Gertrude Stein found so appealing in Anderson's writing of the time became an exemplar of quintessential American style most famously associated with Ernest Hemingway,[90] the expressionistic portrayal of emotional states in Winesburg, Ohio was later, by some critics, considered "undisciplined" and "vague".

[96] Despite criticism that Anderson's "sordid tales"[31] were humorless,[29] and "mired...in plotlessness",[93] Winesburg, Ohio was reprinted several times, selling a total of about 3,000 copies by 1921.

[101] In a 2011 review, Ploughshares praised the book, and specifically highlighted its “in-depth, fearless, summarized description of emotion.”[102] In the 1985 film Heaven Help Us, Danni reads a passage from "Sophistication" to her grief-stricken father.

In the 2003 film The Best of Youth (La meglio gioventù), Matteo Carati borrows Racconti dell'Ohio, the Italian translation of the book, from the library in Rome where he sees Mirella for the second time.

F. Scott Fitzgerald, in his wry reminisence of the Jazz Age, summed up the lesson learned by the book's unsophisticated readers as the fact that "there's a lot of sex around if we only knew it".

[104][105] H. P. Lovecraft said that he wrote the short story "Arthur Jermyn" after he "had nearly fallen asleep over the tame backstairs gossip of Anderson's Winesburg, Ohio.

In the pilot episode of the AMC television series, Fear the Walking Dead, the novel Winesburg, Ohio is picked up in the church used as a drug den, from under a mattress, when character Madison Clark indicates it belongs to her son, Nick.

[110] In the sixth episode of second season of Mad Men, "Maidenform", Duck Phillips walks into the office of William Redd, who quickly puts down his copy of "Winesburg, Ohio".

Nathaniel Halpern, the writer of the 2020 Amazon television series Tales from the Loop, drew inspiration from Winesburg, Ohio, its themes of loneliness and isolation, and its focus on small town characters.

[111] On 3 Aug. 1959, The New York Times announced a film adaptation to be produced by Mirisch Company for release by United Artists, Christopher Sergel to write the screenplay and Jeffrey Hayden to direct.

A stage adaptation of Winesburg, Ohio by Sherwood Anderson (initially in collaboration with playwright Arthur Barton) was performed at the Hedgerow Theatre in Rose Valley, Pennsylvania in 1934.