Winesburg, Ohio

The central irony in the first story of Winesburg, Ohio, “The Book of the Grotesque,” is that the old writer in Winesburg, who tries to explain his vision that the pursuit of truth (or any singular principle) will corrupt the seeker, ultimately finds himself seeking a truth of his own—and becomes just as "grotesque" as the people he critiques:

It was the truths that made the people grotesques. The old man had quite an elaborate theory concerning the matter. It was his notion that the moment one of the people took one of the truths to himself, called it his truth, and tried to live his life by it, he became a grotesque and the truth he embraced became a falsehood.

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In "Godliness, Part I," Anderson steps back in time and tells the story of Jesse Bentley and his family, who run a farm outside Winesburg. Jesse believes his life is imbued with Christian virtue, as he believes he is on a mission sent straight from God, despite the fact that this very self-involvement has led him to neglect his responsibilities as a father and farmer. This is a central source of situational irony in the story:

As time passed and he grew to know people better, he began to think of himself as an extraordinary man, one set apart from his fellows. He wanted terribly to make his life a thing of great importance, and as he looked about at his fellow men and saw how like clod they lived it seemed to him that he could not bear to become also such a clod.

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In "The Strength of God," Reverend Hartman finds himself consumed by lust for Kate. In a moment of particular situational irony, it is only when Hartman finds Kate naked on his bed that he is able to overcome his lust for her and see her full humanity. Anderson uses a religious simile to convey this transformation:

In the room next door a lamp was lighted and the waiting man stared into an empty bed. Then upon the bed before his eyes a naked woman threw herself. Lying face downward she wept and beat with her fists upon the pillow. With a final outburst of weeping she half arose, and in the presence of the man who had waited to look and not to think thoughts the woman of sin began to pray. In the lamplight her figure, slim and strong, looked like the figure of the boy in the presence of the Christ on the leaded window.

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In Anderson’s story "Queer," the ending revolves around the situational irony that Elmer Cowley loathes George Willard despite the fact that George is the only person who's kind enough to see and appreciate Elmer:

George Willard, he felt, belonged to the town, typified the town, represented in his person the spirit of the town. Elmer Cowley could not have believed that George Willard had also his days of unhappiness, that vague hungers and secret unnamable desires visited also his mind. Did he not represent public opinion and had not the public opinion of Winesburg condemned the Cowleys to queerness? Did he not walk whistling and laughing through Main Street? Might not one by striking his person strike also the greater enemy—the thing that smiled and went its own way—the judgment of Winesburg?

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