In film
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.
Daniel Nearing's 2009 independent film Chicago Heights was based on Winesburg, Ohio.
In literature
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".[103]
Ray Bradbury has credited Winesburg, Ohio as an inspiration for his book The Martian Chronicles.[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."[106]
Henry Miller references the book on the first page of his novel Sexus (of The Rosy Crucifixion series).[107]
Amos Oz writes in his autobiography A Tale of Love and Darkness that Winesburg, Ohio had a powerful influence on his writing, showing him that literature must not necessarily always be about heroes. Only after reading Anderson did he find the courage to start writing.[108]
Philip Roth's 2008 novel Indignation is set, in part, at Winesburg College in Winesburg, Ohio. His protagonist holds a part-time job as a waiter at the "New Willard House", evoking the protagonist, George Willard, of Anderson's book.[109]
Porter Shreve presents a possible sequel to Winesburg, Ohio in his novel The End of the Book.
In television
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. Nick is shown reading and discussing the book in season 2, episode 8, which takes its title from the book's opening story.
In the ABC television series, Pretty Little Liars, the book is given to the character Aria Montgomery by her English teacher, Ezra Fitz, with whom she is having an affair. He writes the inscription "When you need to leave Rosewood... Ezra" on the first page.[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".
In the 13th and final episode of the 6th Season of the Netflix series, Orange is the New Black, the character Nicky Nichols is seen carrying a 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]
