Winesburg, Ohio is a collection of loosely connected stories whose central theme is the condition of alienation and isolation which characterizes the human experience. Sherwood Anderson calls his characters "grotesques." Grotesques are individuals who become fixated on any given truth such that he is unable to see beyond it; in his obsession with the truth he has chosen, the individual is rendered incapable of establishing connections with others, and is doomed to live separated from them, isolated and alone. Anderson looks upon his grotesques with pity and with love. He says,
"The grotesques were not all horrible. Some were amusing, some almost beautiful..." ("The Book of the Grotesque").
When an individual reaches maturity, he becomes aware of his own insignificance, and that realization is difficult to accept. In the chapter entitled "Sophistication," George Willard understands
"that in spite of all the stout talk of his fellows he must live and die in uncertainty, a thing blown by the winds, a thing destined like corn to wilt in the sun."
With this realization comes the longing to transcend the condition of aloneness that characterizes mankind for even just one moment, through true communion with another;
"With all his heart (George) wants to come close to some other human, touch someone with his hands, be touched by the hand of another...he wants, most of all, understanding."
The satisfaction of this longing is difficult to achieve, and must, by nature, be fleeting. When it is finally reached, there is a sense of relief, and the quiet acknowledgement that
"I have come to this lonely place and here is this other...Man or boy, woman or girl, they had for a moment taken hold of the thing that makes the mature life of men and women in the modern world possible."
There is a strong connection between Winesburg, Ohio and J. D. Salinger's Catcher in the Rye. The central character in Catcher in the Rye, Holden Caufield, is in the throes of the very condition of alienation described by Anderson in Winesburg, Ohio. Holden is fixated on the truth that people are phony, and his obsession with this idea renders him incapable of establishing meaningful relationships with others. Alone in his grotesqueness, Holden is unable to function at school academically and socially, and as he wanders through New York City, he teeters on the brink of isolation-induced madness.