Who is the worst grotesque in Winesburg, Ohio?

What an interesting question! Of course, to deem any part of a literary work as either the “worst” or the “best” is entirely subjective. Nonetheless, in order to offer up opinions on the subject, it is first important to discuss just what Sherwood Anderson means by “the grotesque” in this bizarre collection of short stories.
In the first book of the collection, “The Book of the Grotesque,” Anderson introduces the reader to “the writer,” an old man who has a dream after climbing into bed one evening. In this dream, he saw a “long procession of figures” appear while on the verge of sleep. He describes these figures as “all grotesques” (22). However, Anderson goes on to describe the grotesque figures not as “all horrible,” but rather a rich mix of “amusing, some almost beautiful” figures (23). The one thing all of these figures have in common is their attachments to the notion of truth. Anderson writes:

"[I]n the beginning when the world was young there were a great many thoughts but no such thing as a truth . . . And then the people came along. Each as he appeared snatched up one of the truths and some who were quite strong snatched up a dozen of them. It was the truths that made the people grotesques.” (23–4)

In this context, it is not their appearance that makes the figures grotesque, but rather their reliance upon various universal truths and then living their lives according to those false doctrines.
So which character is the most grotesque in Anderson’s novel? That is largely up to the reader to decide. One of my personal favorites is Alice Hindman from the story “Adventure.” The truth she snatches up and holds on to for dear life ties to her devotion to her first love, Ned Currie. She waits and waits for Ned to return to her after sending him away to make a life in New York, but even after years of waiting, she refuses to acknowledge that he is never coming back. Instead of reaching out to Ned herself or even moving on with her life with another man, she instead decides that she will “live and die alone” (120). What draws me most to this story is its many feminist implications. A woman who becomes a grotesque over the truth of unrequited love is incredibly interesting and ripe with analytical potential; however, only you can decide which character you deem the “worst grotesque” of the bunch.