Robert E. Sherwood born in 1896 in New Rochelle, New York, Robert was a son of Arthur Murray Sherwood, a rich stockbroker, and his wife, the former Rosina Emmet, a highly accomplished illustrator and portrait painter known as Rosina E. Sherwood. His paternal grandmother was Mary Elizabeth Wilson Sherwood, the author and social leader. He was a great-great-grandson of the former New York State Attorney General Thomas Addis Emmet and a great-grandnephew of the Irish nationalist Robert Emmet, who was executed for high treason after leading the Irish rebellion of 1803, one of a series of attempts to dislodge British rule in Ireland, in 1803. His relatives also included three other notable American portrait artists: his aunts, Lydia Field Emmet and Jane Emmet de Glehn, and his first cousin, once removed, Ellen Emmet Rand. Sherwood was educated at Fay School, Milton Academy and then Harvard University. He fought with the Royal Highlanders of Canada, CEF in Europe during World War I and was wounded. After his return to the United States, he began working as a movie critic for magazines, including Life and Vanity Fair. Sherwood's career as a critic in the 1920s is discussed in the 2009 documentary For the Love of Movies: The Story of American Film Criticism. In this film Time critic Richard Schickel discusses, among other topics, how Sherwood was the first New York critic invited to Hollywood by cross-country train to meet the stars and directors.

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