On the last day of February, 1941, at age 64, Sherwood Anderson set off on a new adventure: he and his fourth wife, Eleanor Copenhaver, sailed on the Santa Lucia on a goodwill mission to South America. The titular spokesman for small-town America, once known around the world for his groundbreaking fictional techniques in Winesburg, Ohio--a man who influenced an entire generation of American writers--intended to get to know his neighbors to the south just as he had those denizens of Ohio about whom he had once so incisively written. He went looking for a Latin American Everyman; he found his own end.

Ben Hecht, an old friend from Anderson's Chicago days and a fellow writer, talked with him shortly before the sailing and published a piece on Anderson's strange mission. In the event, it would serve as both summation of a man's career and as eulogy. Hecht wrote...