by Elizabeth Strout
I'd say Olive Kitteridge is most similar to Winesburg, Ohio, of the books I've read. Both are collections of short stories that have some common settings and characters; in the case of Kitteridge, the titular Olive is at least mentioned in every tale. Both capture the zeitgeist of a small town, though Kitteridge is set in coastal Maine rather than Anderson's Midwest. Both also deal with the tragedies and triumphs of normal life rather than earth-shaking events on a global scale.
I wasn't crazy about Winesburg, finding it repetitive, cliched, sentimental, and overly morose. Kitteridge has some of the same flaws, particularly how depressing many of the stories are, but Strout's just such a good writer and hits on unspoken truths of human existence:
You couldn't make yourself stop feeling a certain way, no matter what the other person did. You had to just wait. Eventually the feeling went away because others came along. Or sometimes it didn't go away but got squeezed into something tiny, and hung like a piece of tinsel in the back of your mind.Kitteridge is dripping with these kinds of poetic observations of modern tragedy. Offsetting the heartbreak is Olive, whose blunt matter-of-factness often serves a humorous counterpoint to the weighty themes.