Born in Worcester, Massachusetts, Benchley's essays were published in collections including Of All Things, Benchley Beside Himself, Inside Benchley, and Chips Off the Old Benchley. His books were illustrated by Gluyas Williams, whose spare, knowing line drawings added to Benchley's success.

Benchley's humor was based on everyday life, news oddities, and absurd, almost surreal essays such as his "Uncle Edith" series. At Harvard, he was a leading contributor to the Harvard Lampoon. With Dorothy Parker and Robert E. Sherwood, his colleagues at Vanity Fair magazine, Benchley formed the Algonquin Round Table. He was an early and regular contributor to the New Yorker Magazine, Life magazine and a humor columnist for the Hearst Corporation Newspapers. His style influenced other humorists such as S. J. Perelman and James Thurber. Benchley is cited as an inspiration by humorists like Bob Newhart, Erma Bombeck, Woody Allen and Shelly Berman and others. The Robert Benchley Society gives an annual humor award in Benchley's honor. Judges of the event include such writers as the Pulitzer Prize-winning humorist Dave Barry who said Benchley influenced him more than anyone other than Barry's own mother.