After the war Benchley worked for the weekly magazine Newsweek as an assistant drama editor. Harcourt, Brace published Benchley's first book in 1950, Side Street, a novel featuring "hilarious activities of two New York City families living in the East Sixties"—that is, living on the East Side of Manhattan near 60th Street. He wrote a biography of his father Robert that McGraw-Hill published in 1955. 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. Benchley was the respected author of much children's fiction that provides readers an experience of certain animal species, historical settings, and so on. 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. Sail a Crooked Ship was adapted as a black-and-white comedy feature film of the same name by Columbia Pictures in 1961. His 1961 novel The Off-Islanders was made into comedy feature The Russians Are Coming, the Russians Are Coming by director/producer Norman Jewison in 1965. The Visitors was adapted as a horror/comedy feature The Spirit Is Willing by Paramount Pictures in 1967. Benchley was a friend of the actor Humphrey Bogart and wrote a Bogart biography published in 1975. Sometime that year, ABC showed the made-for-TV drama Sweet Hostage, based on his 1968 novel Welcome to Xanadu.
Personal life
Benchley and Margaret Bradford were married not long after his college years. They settled in New York City and had two sons, one before and one after World War II. Elder son Peter Benchley was a writer, known best for the novel Jaws and the screenplay for its Steven Spielberg film, the 1975 best-seller Jaws. Younger son Nat Benchley is a writer and actor who has portrayed his grandfather, Robert Benchley, in a one-man, semi-biographical stage show, Benchley Despite Himself. The show was a compilation of Robert Benchley's best monologues, short films, radio rantings, and pithy pieces as recalled, edited, and acted by grandson Nat, combined with family reminiscences and friends' perspectives. Nathaniel Benchley died 1981 in Boston and was interred in the family plot at Prospect Hill Cemetery in Nantucket.
Works
Essays
"Introduction", Twentieth Century Parody, American and British, ed. Burling Lowrey,
Novels
Side Street
A Firm Word or Two
Sail a Crooked Ship
The Off-Islanders
Catch a Falling Spy
A Winter's Tale
The Visitors
The Monument: A Satiric Novel
Welcome to Xanadu
The Wake of the Icarus
Lassiter's Folly
A Necessary End: A Novel of World War II
Sweet Anarchy
Portrait of a Scoundrel
All Over Again
Speakeasy
Non-fiction
The Benchley Roundup: A Selection by Nathaniel Benchley of His Favorites, by Robert Benchley,
Benchley was the writer of at least these 10 books published by Harper & Row in its I Can Read series, several in the History and Mystery subseries. These include eight of his ten "most widely held works" as catalogued by WorldCat libraries.
The Flying Lesson of Gerald Pelican, illus. Mamoru Funai
Feldman Fieldmouse: A Fable, illus. Hilary Knight
Gone and Back – Oklahoma "pioneer adventure of Obediah Taylor, a boy reaching manhood"
The Magic Sled, illus. Mel Furukawa; UK title, The Magic Sledge
Only Earth and SkyLast Forever – "Although recognizing the end of the Indians' freedom is near, a young Cheyenne still chooses to fight with Crazy Horse",
The Deep Dives of Stanley Whale, illus. Mischa Richter
Bright Candles: A Novel of the Danish Resistance – features "a sixteen-year-old Danish boy during the German occupation",
Beyond the Mists: A Novel – features "an adventurous youth who travels to Vinland with Leif Eriksson",
Kilroy and the Gull, illus. John Schoenherr – a Marineland killer whale "escapes to life on the open sea with his friend Morris the sea gull",