Most famously, Woodford authored Trial and Error, which caused something of a scandal at the time of publication because of its no-holds-barred insights into the publishing industry.

Other pen names include Gordon Sayre, Sappho Henderson Britt, and Howard Hogue Kennedy.

His father was a doctor who started a private practice in Sioux City, Iowa, eventually moving it to Chicago.

Woodford witnessed the Eastland disaster where the steamer ship rolled over in the Chicago River and killed 845 people.

Among the many famous contemporaries Woodford befriended, the most notable are H. L. Mencken, writer/satirist James Branch Cabell, novelist Sherwood Anderson, composer George Antheil, and poet Ezra Pound.