In 1916, poet and author Edward Joseph Harrington O'Brien published a book titled "The Best Short Stories of 1915 and The Yearbook of the American Short Story."

The book included what O'Brien considered were the best short stories written by Americans, and which had appeared in American magazines during 1914 and 1915.

O'Brien also included a full accounting of all the short stories written the previous year, not just the stories he chose to republish. This section he referred to as "The Yearbook of the American Short Story", and it included a copious amount of information on the magazines, the publishers and the authors that played a part in the short story genre in America.

O'Brien then published a new book every year, in which he republished what he felt were the best short stories that had appeared in American magazines during the previous year. He also provided a full detailing of all the short stories written, as part of the "yearbook" section.

Each year, the title of the book was "The Best Short Stories of [YYYY] and The Yearbook of the American Short Story."

O'Brien died in February of 1941, but the publisher, Houghton Mifflin, kept the series going with a new editor, Martha Foley. Foley had been friends with O'Brien, and was editor, along with her husband Whit Burnett, of "Story Magazine".

After Martha Foley took over the series, it was renamed "The Best American Short Stories [YYYY]".

Foley was editor from 1942 to 1977 and for part of that time, her son David Burnett also helped edit the annual publication.

Foley died in 1977, and again, the publisher, Houghton Mifflin, kept the series going.

However, instead of having the same person edit the book each year, they began to invite a different prominent author to "guest edit" the series each year.

Beginning with the 1978 publication, many well-known authors have chosen the stories for "their year", and written an introduction, giving their personal thoughts about each story.