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.
If ever the collection of stories contained an admission of nihilism, it would be this. By this darkened worldview, truths once held to be absolute and unassailable become flimsy and untrustworthy, and the attempt to pursue such a truth becomes a foolhardy descent into some kind of madness. Such is the psychological struggle that the old writer finds himself caught in, and throughout the rest of the collection, readers will find themselves face to face with a number of other “grotesques”: the citizens of Winesburg, lost in their own vain pursuits of meaning and truth. The central narrative of the novel, George Willard’s coming of age, is therefore also the story of his confrontations with these "grotesques" as he tries to find his own sources of meaning—ones that might be generous and open-ended enough to save him from this fate.
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.
Unfortunately for Jesse, in his efforts to distinguish himself from his “fellow men,” he becomes far worse than the “clods” that they may be. His failure comes by way of his arrogance and insistent self-importance—his pursuit of meaning through his faith, which he thinks has given him divine purpose but in fact has driven him away from his family’s needs and his own. The irony here is that Jesse embraces the ideologies of Christianity as a source of meaning while utterly failing to act with a shred of Christian virtue.
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.
Suddenly, Hartman is unable to ignore Kate's humanity because of her physical similarity to a Christian boy depicted in some imaginary stained-glass window. By comparing Kate to religious iconography, Hartman casts aside his lust and finds his prayer once again. Faith is a confusing and fickle force in Winesburg, Ohio, and it ultimately leads characters into some sort of sinful temptation at least as often as it helps them recover from such things—but in this case, Hartman's faith appears to save him from himself.
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?
Although Elmer sets out against George, George is actually the one and only resident of Winesburg not predisposed to judging or dismissing Elmer. George is not the embodiment of judgement but the absolute opposite. Elmer is desperate for connection, and George is the one person most likely to be able to befriend him (and the only person who even wants to), but Elmer nonetheless pushes him away. This is a prime example of the sort of banal, melancholic self-destructive behavior that drives so much of the alienation that Anderson explores in the characters of Winesburg.
