[2] Born in Newton, Massachusetts to a literary family, he was the son of Robert Benchley (1889–1945), a noted American writer, humorist, critic, and actor and one founder of the Algonquin Round Table in New York City, and Gertrude Darling.
In 1960 Harper & Row published his second novel, Sail A Crooked Ship, and Random House his first children's book, retold from Sindbad the Sailor with illustrations by Tom O'Sullivan.
[6] Benchley was the respected author of much children's fiction that provides readers an experience of certain animal species, historical settings, and so on (Oscar Otter, Sam The Minuteman, etc).
He presented diverse locales and topics: for instance, Bright Candles recounts the experiences of a 16-year-old Danish boy during the German occupation of Denmark in World War II; Small Wolf features a Native American boy who meets white men on the island of Manhattan and learns that their ideas about land are different from those of his own people.
The show was a compilation of Robert Benchley's best monologues, short movies, radio rantings, and pithy pieces as recalled, edited, and acted by grandson Nat, combined with anecdotes, family reminiscences and friends' perspectives.