Sherwood was one of the original members of the Algonquin Round Table. He was close friends with Dorothy Parker and Robert Benchley, who were on the staff of Vanity Fair with Sherwood when the Round Table began meeting in 1919. Author Edna Ferber was also a good friend.
Sherwood stood six feet eight inches tall. Dorothy Parker, who was five-feet four-inches, once commented that when she, Sherwood, and Robert Benchley (who was six feet tall) would walk down the street together, they looked like "a walking pipe organ." When asked at a party how long he had known Sherwood, Robert Benchley stood on a chair, raised his hand to the ceiling, and said, "I knew Bob Sherwood back when he was only this tall."
Sherwood's first play, The Road to Rome in 1927 was greeted with success. The play is a comedy concerning Hannibal's botched invasion of Rome. One of the underlying themes of this work is the stupidity of war. This is a recurrent motif in many of his dramatic works including his Idiot's Delight of 1936 which won the first of his four Pulitzer Prizes. According to legend, he once admitted to the gossip columnist Lucius Beebe: “The trouble with me is that I start with a big message and end up with nothing but good entertainment.”
In addition to his work for the stage, Sherwood also was in demand in Hollywood. He began writing for the silver screen in 1926. While some of his work is uncredited, his films include many adaptations of his plays.
Robert E. Sherwood worked with Alfred Hitchcock and Hitchcock's assistant Joan Harrison in Rebecca (1940). Robert E. Sherwood and Joan Harrison wrote the screenplay for Rebecca. Robert E. Sherwood's close friends Robert Benchley and Dorothy Parker also worked with Alfred Hitchcock. Robert Benchley played Stebbins in Alfred Hitchcock's Foreign Correspondent (1940). Alfred Hitchcock allowed Benchley to write his own lines for his character Stebbins. And Dorothy Parker worked with Alfred Hitchcock as screenwriter in Saboteur (1942).
With Europe in the midst of World War II, Sherwood changed his anti-war stance and supported American involvement against the Third Reich. His 1940 play, There Shall Be No Night told the story of the Russian invasion of Finland. The play was produced by the Theatre Guild in 1940 and starred Alfred Lunt and Lynn Fontanne and featured Montgomery Clift. A TV Adaptation was broadcast on NBC on March 17, 1957 produced by and starring the actress Katharine Cornell .
His patriotism led him to work as a speechwriter for President Franklin D. Roosevelt. He recounted this period with his book Roosevelt and Hopkins which won a Pulitzer Prize and a Bancroft Prize in 1949.
Sherwood is credited with originating the phrase which came to be shortened as the 'arsenal of democracy' and later used by Franklin Roosevelt in his speeches. Sherwood had been quoted on May 12, 1940 by the New York Times, "this country is already, in effect, an arsenal for the democratic Allies." Although the French economist, Jean Monnet had allegedly used the phrase later in 1940, "arsenal of democracy," he was urged not to use it again so Franklin Roosevelt could make use of it in his speeches.
Sherwood also served for a time as Director of the Office of War Information. He returned to dramatic writing after the war and produced his memorable script for the film The Best Years of Our Lives which was directed by William Wyler. The 1946 film explores how the lives of three servicemen have been changed after they return home from war. For this film, Sherwood was given an Academy Award for Best Screenplay.
Sherwood died of a heart attack in New York City in 1955.
A production of his work Small War on Murray Hill debuted at the Ethel Barrymore Theatre on January 3, 1957.
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