Author of Winesburg, Ohio, Marching Men, Poor White, Many Marriages, and Dark Laughter
Born in an Ohio farm town of no significance to a Union vet father and probably exhausted mother of seven. The family started off stable enough, but soon began fleeing from small town to small town by Sherwood’s first birthday. His father’s family debt hounded them for years, and years more once dad picked up drinking to remedy his issues.
Still in childhood, Sherwood started picking up odd jobs like newspaper slanging and shit shoveling before dropping out of school around age 14. Despite being a drop out, he still spent most of his free time reading, but then again, what else was there to actually do in the late 19th century hinterlands.
The year he turned 18, it all went to hell. Mom died of consumption and dad started disappearing on benders for weeks at a time. Sherwood took a job at a stable that allowed him to sleep in the hayloft above the horses. By age 19 he gave up on the small town life and hoofed it to Chicago where his oldest brother was laughing his way through art school. There he started attending night classes on business math and poetry, but he cut out early to try his luck as a soldier in the Spanish-American War. As it happened, he didn’t end up needing any luck because everywhere his company got sent to had concluded what fighting was to be done months before their arrival. But, at least, he made a lot of friends due to his literacy, which allowed him to read dime novels to bored troops, and his charm, which allowed him to woo many women.
After the war, he completed his education, graduating with top marks at the turn of the century. After, he returned to Chicago with a job offer in advertising, but he hated his boss and hated office life even more, so he left to write ad copy for a trade magazine that sold agricultural tools. It was here that he began writing creatively. After all, when God gives you lemons, you write a sardonic vignette about the ghoulish lemonade seller. Being junior level, Sherwood couldn’t just sit and go extra hard on whimsical ad copy all day. His job compelled him to wander the dirtways of Illinois and Ohio trying to drum up new clients to buy the magazine’s ad space. While on one of these jaunts, he met a wealthy heiress that would become his wife.
On the Labor Day of his 30th year, an opportunity to run a mail-order catalogue was dropped into his lap. He moved his young family to their new happy home in Cleveland, Ohio; the city of burning rivers and rock & roll. But they wouldn’t stay happy, or at least, he wouldn’t. Part of his company’s gimmick was that Sherwood, being president, guaranteed full satisfaction on all the catalogue’s products. After one of the manufacturers under the umbrella sent out a large number of defective egg hatchers, Sherwood was flooded with a cavalcade of unending hate-mail, all of it addressed directly to him. It happened about a year after this wonderful opportunity had opened for him, and it ended with a nervous breakdown. The family left Cleveland for the two-horse town of Elyria.
The Andersons bounced back quick enough. Sherwood spun up a new mail-order company selling some kind of magical paint, and his wife birthed a couple of healthy babies. The business hit a tipping point, and Sherwood bought up a bunch of smaller mail-order businesses. By the time he was 35 he had merged them all into one, the American Merchants Company, which he ran as a profit-sharing investment firm, a novelty structure that he called “Commercial Democracy”.
Sherwood was objectively winning at life, but the glory days wouldn’t last long. In the next year, 1912, he may or may not have suffered the motherlode of all nervous breakdowns. The story has an odd bit of self-authoring.
- The Secretary’s Account: Sherwood came to the office, started dictating a business letter to her, then spaced out. He mumbled, “I feel as though my feet were wet, and they keep getting wetter.” Then he walked out.
- The Pharmacist’s Account: After disappearing for several days, Sherwood stumbled into a drug store all the way over in Cleveland and asked the pharmacist to help him figure out who he was. While Anderson babbled on the pharmacist managed to get his phone book out of his pocket and called someone from the front page. This ended up being a member of Elyria’s Chamber of Commerce, who came to the shop and recognized Sherwood immediately. This man scooped him up and handed him over to the hospital in downtown Cleveland. When Sherwood’s wife arrived, he didn’t recognize her.
- Sherwood’s Account: In his memoir published in 1942 he claimed, “I wanted to leave, get away from business… I resorted to slickness, to craftiness… The thought occurred to me that if men thought me a little insane they would forgive me if I lit out…” Many were and are skeptical of his claims that he intentionally feigned temporary insanity because his justification was that his work and family would never accept his desire to write. His creative interests were no secret at the time. His wife, his secretary, and several business associates knew he dabbled in fiction projects both on and off the clock. Nonetheless, he came a hero to young mid-century men for escaping the humdrum life of materialism.
Shortly after this episode, he divorced his wife and moved back to Chicago. She wouldn’t be the last. Right after ending this eight year marriage, he married a sculptor, who he would divorce eight years later. In that same year, he married the girl he would move to New Orleans with, and they also divorced after eight years. A year later he married another woman, and they didn’t divorce because he died about eight years after their marrying. The guy is a top tier candidate for a study of the seven-year itch.
Anyway, after his divorce and move to Chicago he wrote three books in three years. The first two flopped like fish out of water, but the third Winesburg, Ohio, made him famous. The books that came after were also successful. Among the last few, Many Marriages and Dark Laughter celebrated the shiny new sexual freedom of the Roaring Twenties, which speaks to a fixation (do you know how hard it is to write a whole fucking book?) that makes these last couple of paragraphs make a whole lot more sense.
In the mid-1920s he moved to New Orleans with Wife No. 3 and became an influential mentor figure in the young literati scene of the French Quarter. Faulkner was in awe of him while Hemingway wrote an entire satire about him (The Torrents of Spring). Sherwood didn’t write much of anything remarkable after these halcyon days. His own story came to an end while on a cruise down the South American coast with Wife No. 4 in 1941. Somehow he swallowed a whole toothpick while eating dinner and after several days of debilitating tummy aches he finally debarked in Panama. There he died of inflammation caused by the internal damage of destiny’s toothpick.




