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.

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.”[4] Sherwood was actively engaged with the advocacy for writers' rights within the theatre world.

There Shall Be No Night, his 1940 play about the Soviet Union's invasion of Finland, was produced by the Playwright's Company that he co-founded, and it starred Alfred Lunt, Lynn Fontanne, and Montgomery Clift.

[8] Sherwood is credited with originating the phrase that eventually evolved to "arsenal of democracy", a frequent catchphrase in Roosevelt's wartime speeches.

The 1946 film, which explores changes in the lives of three soldiers after they return home from war, earned Sherwood an Academy Award for Best Screenplay.

In 1949, comedian Groucho Marx also commented about Sherwood's height during a filmed radio broadcast of the quiz show You Bet Your Life.

Groucho, who hosted the popular series, interviewed in one episode American football player Howard Scala, a member of the NFL's Green Bay Packers.

Impressed by Scala's own considerable height, Marx shared the following anecdote with the show's audience:Reminds me of Bob Sherwood, the playwright, he's an old friend of mine; and he's six-foot-five and very thin.

A production of Small War on Murray Hill, his final work, debuted on Broadway at the Ethel Barrymore Theatre on January 3, 1957.