Sherwood Berton Anderson was born on September 13, 1876, in Camden, Ohio, a farming town with a population of around 650 (according to the 1870 census). He was the third of seven children born to Emma Jane (née Smith) and former Union soldier and harness-maker Irwin McLain Anderson. Considered reasonably well-off financially, Anderson’s father was seen as an up-and-comer by his Camden contemporaries, the family left town just before Sherwood’s first birthday. Reasons for the departure are uncertain; most biographers note rumors of debts incurred by either Irwin or his brother Benjamin. The Andersons headed north to Caledonia by way of a brief stay in a village of a few hundred called Independence (now Butler). Four or five years were spent in Caledonia, years which formed Anderson’s earliest memories. This period later inspired his semi-autobiographical novel Tar: A Midwest Childhood (1926). In Caledonia Anderson’s father began drinking excessively, which led to financial difficulties, eventually causing the family to leave the town.

With each move, Irwin Anderson’s prospects dimmed; while in Camden he was the proprietor of a successful shop and could employ an assistant, but by the time the Andersons finally settled down in Clyde, Ohio in 1884, Irwin could only get work as a hired man to harness manufacturers. That job was short-lived, and for the rest of Sherwood Anderson’s childhood, his father barely supported the family as an occasional sign-painter and paperhanger, while his mother took in washing to make ends meet. Partly as a result of these misfortunes, young Sherwood became adept at finding various odd jobs to help his family, earning the nickname “Jobby.”

By Anderson’s 18th year in 1895, his family was on shaky ground. His father had started to disappear for weeks. Two years earlier, in 1893, Karl, Sherwood’s elder brother, had left Clyde for Chicago. On May 10, 1895, his mother succumbed to tuberculosis. Sherwood, now essentially on his own, boarded at the Harvey & Yetter’s livery stable where he worked as a groom—an experience that would translate into several of his best-known stories. (Irwin Anderson died in 1919 after having been estranged from his son for two decades.) Two months before his mother’s death, in March 1895, Anderson had signed up with the Ohio National Guard for a five-year hitch while he was going steady with Bertha Baynes, an attractive girl and possibly the inspiration for Helen White in Winesburg, Ohio, and he was working a secure job at the bicycle factory. But his mother’s death precipitated the young man’s leaving Clyde. He settled in Chicago around late 1896 or spring/summer 1897, having worked a few small-town factory jobs along the way.

Anderson moved to a boardinghouse in Chicago owned by a former mayor of Clyde. His brother Karl lived in the city and was studying at the Art Institute. Anderson moved in with him and quickly found a job at a cold-storage plant. In late 1897, Karl moved away, and Anderson relocated to a two-room flat with his sister and two younger brothers newly come from Clyde. Money was tight—Anderson earned “two dollars for a day of ten hours”— but with occasional support from Karl, they got by. Following the example of his Clyde confederate and lifelong friend Cliff Paden (later to become known as John Emerson) and Karl, Anderson took up the idea of furthering his education by enrolling in night school at the Lewis Institute. He attended several classes regularly including “New Business Arithmetic” earning marks that placed him second in the class. It was also there that Anderson heard lectures on Robert Browning, Alfred Tennyson, and was possibly first introduced to the poetry of Walt Whitman. Soon, however, Anderson’s first stint in Chicago would come to an end as the United States prepared to enter the Spanish–American War.

Although he had limited resources while in Chicago, Anderson bought a new suit and returned to Clyde to join the military. Once home, the company he joined mustered into the army at Camp Bushnell, Ohio on May 12, 1898. Several months of training followed at various southern encampments until early in 1899, when his company was sent to Cuba. Fighting had ceased four months prior to their arrival. On April 21, 1899, they left Cuba having seen no combat. According to Irving Howe, “Sherwood was popular among his army comrades, who remembered him as a fellow given to prolonged reading, mostly in dime westerns and historical romances, and talented at finding a girl when he wanted one. For the first of these traits he was frequently teased, but the second brought him the respect it usually does in armies.”

After the war, Anderson resided briefly in Clyde performing agricultural work before deciding to return to school. In September 1899 Anderson joined his siblings Karl and Stella in Springfield, Ohio where, at the age of twenty-three he enrolled for his senior year of preparatory school at the Wittenberg Academy, a preparatory school located on the campus of the Wittenberg University. In his time there he performed well, earning good marks and participating in several extracurricular activities. In the spring of 1900 Anderson graduated from the Academy, offering a discourse on Zionism as one of the eight students chosen to give a commencement speech.

Anderson and Cornelia Lane married in 1904 and divorced in 1916 after having his only 3 children.

Part of Anderson’s job in those early years of his career was making trips to solicit potential clients. On one of these trips around May 1903 he stopped in the home of a friend from Clyde, Jane “Jennie” Bemis, then living in Toledo, Ohio. It was there that he met Cornelia Pratt Lane (1877–1967), the daughter of wealthy Ohio businessman Robert Lane. The two were married a year later, on the 16th of May, in Lucas, Ohio. They would go on to have three children—Robert Lane (1907–1951), John Sherwood (1908–1995), and Marion (aka Mimi, 1911–1996). After a short honeymoon, the couple moved into an apartment on the south side of Chicago. For two additional years, Anderson worked for Long-Critchfield until an opportunity came along from one of the accounts he managed and so on Labor Day 1906, Sherwood Anderson left Chicago for Cleveland to become president of United Factories Company, a mail-order firm selling various items from surrounding firms.

His failure in Cleveland did not delay him for long, however, because in September 1907, the Andersons moved to Elyria, Ohio, a town of approximately ten thousand residents, where he rented a warehouse within sight of the railroad and began a mail-order business selling (at a markup of 500%) a preservative paint called “Roof-Fix.” The first years in Elyria went very well for Anderson and his family; two more children were added for a total of three in addition to a busy social life for their parents. So well, in fact, did the Anderson Manufacturing Co. do that Anderson was able to purchase and absorb several similar businesses and expand his firm’s product-lines under the name Anderson Paint Company. Carrying on that momentum, in late 1911 Anderson secured the financial backing to merge his companies into the American Merchants Company, a profit-sharing/investment firm operating in part on a scheme he developed around that time called “Commercial Democracy.”

Anderson’s first novel, Windy McPherson’s Son, was published in 1916 as part of a three-book deal with John Lane. This book, along with his second novel, Marching Men (1917), are usually considered his “apprentice novels” because they came before Anderson found fame with Winesburg, Ohio (1919) and are generally considered inferior in quality to works that followed.

Anderson quickly married Tennessee Claflin Mitchell in 1916 and obtained a divorce Reno, Nevada in 1924.

Although his short stories were very successful, Anderson wanted to write novels, which he felt allowed a larger scale. In 1920, he published Poor White, which was rather successful. In 1923, Anderson published Many Marriages; in it he explored the new sexual freedom, a theme which he continued in Dark Laughter and later writing. Dark Laughter had its detractors, but the reviews were, on the whole, positive. F. Scott Fitzgerald considered Many Marriages to be Anderson’s finest novel.

After having moved back to Chicago, Anderson formally divorced Cornelia. Later, he married his mistress, the sculptor Tennessee Claflin Mitchell (1874–1929). Anderson divorced Mitchell in 1924 in Reno, Nevada, and soon the same year married his third wife, Elizabeth Prall, a woman he was already involved with before the divorce.

Beginning in 1924, Sherwood and Elizabeth Prall Anderson moved to New Orleans, where they lived in the historic Pontalba Apartments (540-B St. Peter Street) adjoining Jackson Square in the heart of the French Quarter. For a time, they entertained William Faulkner, Carl Sandburg, Edmund Wilson and other writers, for whom Anderson was a major influence. Critics trying to define Anderson’s significance have said he was more influential through this younger generation than through his own works.

In his later years, Anderson and Copenhaver lived on his Ripshin Farm in Troutdale, Virginia, which he purchased in 1927 for use during summers. While living there, he contributed to a country newspaper, columns that were collected and published posthumously.

That year Anderson married Elizabeth Norma Prall (1884–1976), a friend of Faulkner’s whom he had met in New York. After several years that marriage also failed. In 1928 Anderson became involved with Eleanor Gladys Copenhaver (1896–1985).

In the 1930s, Anderson published Death in the Woods (short stories), Puzzled America (essays), and Kit Brandon: A Portrait (novel). In 1932, Anderson dedicated his novel Beyond Desire to Copenhaver. Although by this time he was considered to be less influential overall in American literature, some of what have become his most quoted passages were published in these later works. The books were otherwise considered inferior to his earlier ones.

In 1933, Anderson and Copenhaver married. They traveled and often studied together. They were both active in the trade union movement. Anderson also became close to Copenhaver’s mother, Laura.

Anderson frequently contributed articles to newspapers. In 1935, he was commissioned to go to Franklin County, Virginia to cover a major federal trial of bootleggers and gangsters, in what was called “The Great Moonshine Conspiracy”. More than 30 men had been indicted for trial. In his article, he said Franklin was the “wettest county in the world,” a phrase used as a title for a 21st-century novel by Matt Bondurant.

Anderson died on March 8, 1941, at the age of 64, taken ill during a cruise to South America. He had been feeling abdominal discomfort for a few days, which was later diagnosed as peritonitis. Anderson and his wife disembarked from the cruise liner Santa Lucia and went to the hospital in Colón, Panama, where he died on March 8. An autopsy revealed that a swallowed toothpick had done internal damage resulting in peritonitis.