Robert Emmet Sherwood was the product of an affluent and artistic family. His mother, the former Rosina Emmet, was sufficiently well known as an artist to be listed in Who’s Who. His father, Arthur Murray Sherwood, was a prominent investment broker and held a seat on the New York Stock Exchange. Arthur Sherwood was a frustrated actor and had been an active member of the Hasty Pudding Club during his student days at Harvard, where he was also the first president of the Harvard Lampoon. Robert Sherwood followed in his father’s footsteps at Harvard, both as a member of the Hasty Pudding Club and as editor of the Lampoon.
Sherwood was named for the Irish patriot Robert Emmet, brother of his mother’s great-grandfather, who led an attack on Dublin Castle and was hanged in 1803. Sherwood was proud of his renegade namesake. Mary Elizabeth Wilson Sherwood, mother of Sherwood’s father, had been honored both by the French government and by Queen Victoria of Britain. She was active in literary and artistic circles and in her lifetime wrote more than twenty books and hundreds of articles.
Thus, Robert Sherwood, the next to the youngest of five Sherwood children, was born into an artistically active family of considerable means. Shortly after his birth, the family moved to a house on Lexington Avenue in New York City. The family also maintained a forty-room Georgian mansion, Skene Wood, set on three hundred acres bordering Lake Champlain. It was there that Sherwood spent most of his childhood summers.
During the summers at Skene Wood, Sherwood and his siblings put on amateur dramatic productions, and Sherwood produced a handwritten newspaper, Children’s Life. At eight, he wrote an ending for Charles Dickens’s unfinished novel The Mystery of Edwin Drood (1870), and two years later he wrote his first play, Tom Ruggles’ Surprise, soon to be followed by How the King Was Saved and The Curse of Bacchus.
When he was nine years old, Sherwood was sent to the Fay School in Southborough, Massachusetts, and at thirteen, he was sent to the Milton Academy near Boston to begin his preparatory studies for Harvard. Both in preparatory school and later at Harvard, Sherwood’s energies were to be directed more toward literary matters than toward academic ones. He was managing editor of Milton’s monthly magazine, Orange and Blue, for much of his final year at Milton; he was deeply in trouble with his studies, however, and in April, the school forced his withdrawal from this post. Ultimately, his grades were so low that Milton Academy refused him a diploma, giving him instead a certificate of attendance. Despite this, Sherwood was elected valedictorian by his classmates, and he gave the valedictory address.
Sherwood’s academic career at Harvard was no more distinguished than his career at Milton Academy had been, although his contributions to Harvard’s dramatic and literary clubs were substantial. On the brink of expulsion three times during his freshman year alone, Sherwood did not make it through to graduation. In July of 1917, having been rejected on account of his great height by the various branches of the United States armed forces in which he attempted to enlist, Sherwood became a member of the Canadian Expeditionary Force, serving in the Forty-second Battalion of the Fifth Royal Highlanders and achieving the distinction of being very probably the tallest serviceman in World War I to wear kilts. At six feet, seven inches, he towered over his fellow combatants. He served six months in France, where he was gassed on Vimy Ridge. In 1918, Harvard awarded him a bachelor’s degree in absentia although he had not met the academic standards for this degree.
On his return from the war, Sherwood was offered a position at Vanity Fair, a magazine that the Lampoon under Sherwood’s editorship had burlesqued so effectively that its editor wanted Sherwood on his staff. At Vanity Fair , Sherwood shared an office with Robert Benchley and Dorothy Parker. The three were...
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