Robert E. Sherwood was born in 1896, and honestly, he was a giant in every sense. He stood six-foot-eight. He was so tall that when he walked down 44th Street with Dorothy Parker and Robert Benchley, Parker joked they looked like a "walking pipe organ."
But the height wasn't the half of it.
Most people today have no clue who he is. That’s a shame. This guy didn't just write plays; he basically wrote the script for 20th-century American liberalism. He won four Pulitzers. He won an Oscar. He wrote FDR’s speeches and helped launch the Voice of America. Not bad for a guy who got kicked out of Harvard for failing everything except the theater stuff.
Robert E. Sherwood Born into New Rochelle Royalty
Robert Emmet Sherwood entered the world on April 4, 1896, in New Rochelle, New York. His family was kind of a big deal. His mother, Rosina Emmet Sherwood, was an accomplished artist. His father, Arthur Murray Sherwood, was a wealthy stockbroker.
He grew up in a world of 40-room mansions and summers on Lake Champlain. It sounds fancy because it was.
But Sherwood wasn't some idle rich kid. He was obsessed with writing. By age eight, he was trying to finish Charles Dickens’s The Mystery of Edwin Drood. By ten, he’d written his first original play. He was essentially born to be at the center of the literary world.
Still, school was a disaster.
He went to the Fay School and then Milton Academy. He was brilliant at writing for the school papers, but he absolutely bombed his classes. He somehow made it into Harvard, only to be placed on probation almost immediately. He spent more time drinking at local pubs and watching movies than studying Greek or Algebra.
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Then the war happened.
The War That Changed Everything
When World War I broke out, Sherwood tried to join the U.S. Army. They rejected him. Why? He was too tall. Apparently, being 6'8" made you a walking target in a trench.
He didn't give up. He went north and joined the Canadian Black Watch.
He saw the worst of it. He was gassed at Arras. He was wounded in action. He spent months in a hospital bed. When Robert E. Sherwood born into a life of privilege finally returned home, he wasn't the same guy. He came back an "ardent pacifist."
That trauma defined his early career.
He landed a job as a drama critic for Vanity Fair and later Life. This is where he became a founding member of the legendary Algonquin Round Table. He hung out with the smartest, meanest wits in New York. Dorothy Parker. Robert Benchley. Harpo Marx.
The Playwright Who Switched Sides
His first big hit was The Road to Rome in 1927. It was a comedy about Hannibal, but really, it was an anti-war manifesto. People loved it.
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Throughout the 1930s, he kept winning.
- Idiot’s Delight (1936) – Pulitzer Prize #1.
- Abe Lincoln in Illinois (1939) – Pulitzer Prize #2.
But then Hitler started moving across Europe.
Sherwood’s pacifism broke. He realized that some things are worse than war, and totalitarianism was one of them. He wrote There Shall Be No Night (1940), a play about the Soviet invasion of Finland. It was a call to arms. It won him his third Pulitzer, but it also cost him friends who thought he’d betrayed his anti-war roots.
One guy who didn't mind? Franklin D. Roosevelt.
FDR read the play and loved it. Soon, Sherwood was in the White House. He became one of the "ghosts" behind Roosevelt’s Fireside Chats. He helped craft the "Arsenal of Democracy" speech.
Think about that. The guy who was gassed in WWI and spent a decade preaching peace was now the man helping the President sell World War II to the American public.
The Best Years and the Final Act
After the war, Sherwood didn't just go back to Broadway. He went to Hollywood.
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He wrote the screenplay for The Best Years of Our Lives (1946). It’s a gut-wrenching movie about three veterans coming home and realizing they don’t fit in anymore. It was basically his own life story on screen. It won him an Oscar.
Then he wrote Roosevelt and Hopkins in 1948. It’s a massive biography of the relationship between the President and his closest advisor. Boom. Pulitzer Prize #4.
He died in 1955 of a heart attack at only 59.
Why You Should Care Today
Sherwood’s life is a masterclass in how to evolve. He wasn't afraid to change his mind when the world changed around him. He went from a privileged kid to a broken soldier, from a cynical wit to a national voice of conscience.
If you want to understand the grit behind the "Greatest Generation," you have to look at Sherwood.
Actionable Insights from Sherwood’s Career:
- Don’t fear the pivot. Sherwood was a die-hard pacifist until he saw a greater evil. Being "consistent" is less important than being right when it matters.
- Use your "disadvantage." His height got him rejected by his own country’s army, so he fought for another. He used that perspective to write the best war-return movie ever made.
- Collaborate with wits. He surrounded himself with people like Dorothy Parker who challenged him. You’re only as good as the room you’re in.
- Write for the moment. His best plays weren't just "art"—they were responses to what was happening in the news that week.
If you’ve never seen The Best Years of Our Lives or read The Petrified Forest, go find them. They aren't just museum pieces. They’re the heartbeat of an era that Robert E. Sherwood helped define.