Sherwood Anderson was born Sept. 13, 1876, in Camden, Ohio, the third child of seven born to a harnessmaker and his wife. The family moved often, settling in Clyde, Ohio in 1884. Sherwood didn't spend much time in school; he was nicknamed "Jobby" as a young boy due to the numbers of odd jobs he took on instead to help support his family. After his mother's early death in 1895 Anderson moved to Chicago for a couple of years, until he joined the army and was an infantryman in Cuba during the Spanish-American War. After his service he moved to Springfield, Ohio and enrolled in Wittenberg College for a year (1899-1900), where he met a friend who found him a job as an advertising copywriter and space salesman for Long-Critchfield Company in Chicago. In 1906 he moved with his first wife, Cornelia Lane Anderson, to Cleveland, Ohio, to set up a mail order house. A year later he established his own mail order paint business in Elyria, Ohio. It was there on Nov. 27, 1912 that Anderson suddenly left his office and wandered the countryside for four days, until he was found and hospitalized for exhaustion. Whether this incident was a nervous breakdown or a veiled attempt to leave his business and family to pursue a more artistic lifestyle is still under speculation. Whatever the reason, he soon left Ohio for good and moved back to Chicago to work again for the Long-Critchfield Company. This time, however, he was determined to also be a novelist, and joined the Chicago literary and journalist circles, which included Margaret Anderson of the Little Review, Harriet Monroe of Poetry Magazine, and writers Ben Hecht and Carl Sandburg. He began publishing short stories and poetry regularly in the aforementioned magazines, and his novel-writing career began in 1916 with the publication of Windy McPherson's Son. His real fame as a writer came in 1919, with the publication of his classic work, Winesburg, Ohio.

From the late 1910s through the mid 1920s, Anderson moved frequently, to New York City, Fairhope Alabama, New Orleans, Reno Nevada, and back to New Orleans. He met Gertrude Stein and James Joyce on his first trip to Paris in 1921, and remained friends with Stein for the rest of his life. In 1922 he befriended William Faulkner in New Orleans; Faulkner considered Anderson a mentor. In 1926 he bought a home near Marion, Virginia, which he named "Ripshin" (after a nearby creek of the same name) and, aside from travelling, lived there for the rest of his life. With money borrowed from his patron Burton Emmett, he bought two newspapers in Marion, the Marion Democrat and the Smyth County News. From this time forward he continued to write novels, short stories, autobiographical works, articles in his newspapers, and essays in other publications.

Anderson was married four times: To Cornelia Lane (1904-1916), with whom he had two sons and a daughter; to artist and music teacher Tennessee Mitchell (1916-1924); to Elizabeth Prall (1924-1932); and to Eleanor Copenhaver (1933-1941). Copenhaver, an executive with the YWCA, was interested in labor conditions in the South, and was inspiring to Anderson in terms of topics for his articles on social justice and the plight of the American workingman and African Americans. In early 1941, he embarked on the S.S. Santa Lucia with Eleanor, Thornton Wilder, and others on an unofficial good-will tour of South America. He became gravely ill at sea, was taken to a hospital in Colon, in the Panama Canal Zone, and died of peritonitis on March 8, 1941. The newspaper accounts reported one month later that before embarking on his trip, he apparently accidentally ingested a wooden toothpick, which pierced the abdominal wall and caused the fatal infection.