Sherwood's first Broadway play, "The Road to Rome" (1927), a comedy concerning Hannibal's botched invasion of Rome, introduced one of his favorite themes: the futility of war. Many of his later dramatic works employed variations of this theme, including "Idiot's Delight" (1936), which won Sherwood the first of 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.”