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"The Winthrop Covenant" by Louis Auchincloss is a really well-written and interesting collection of short stories. It's one I can return to over the years and get fresh enjoyment out of each time.
I always enjoy The Best American Short Story annual collections. There are typically a few in each collection that are perfect for me. I like short stories from different authors rather than a collection of one author's works.
George Saunders always has great short story collections. His latest, Tenth of December, was nominated for a National Book Award, and the New York Times Magazine declared it the best book you'll read all year. It was good. He has several collections, all very good. Kind of weird, but extremely hilarious. Many of his stories appear in the New Yorker.
I'm not a fan of short stories, but in a pinch, I've liked Kurt Vonnegut's Welcome to the Monkey House, John Sayles' The Anarchists' Convention, and also collections by Roald Dahl, and science fiction like Ray Bradbury. If he's a literary type, maybe Guy de Maupassant and Saki.
The World of the Short Story, edited by Clifton Fadiman. With each story, Mr Fadiman talks about the author and why he is important to the world of literature. Sometimes he also analyzes the story a bit. All this is done in one short page and then comes the story, each story a fast read when short of time. It is a very good collection with many authors I never heard of.
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