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 "". 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.