James Montgomery Flagg was born in New York in 1877. He started drawing as a child and at the age of twelve had his first drawing accepted by a national magazine. Two years later he was contributing art, prints and poster to Life Magazine and at fifteen was on the staff of the The Judge. Flagg studied at the Arts Students League (1894-98) in New York and when he was twenty spent a year working in London before moving on to France.
By the beginning of the 20th century Flagg was one of America's leading illustrators. In 1903 he began drawing portraits of Hollywood stars for Photoplay magazine. Other magazines that published his art, prints and posters included McClure's Magazine, Collier's Weekly, Ladies' Home Journal, Cosmopolitan, Saturday Evening Post and Harper's Weekly. Flagg also illustrated a large number of books including Yankee Girls Abroad (1900), An Orchard Princess (1905), Simon the Jester (1909) and The Adventures of Kitty Cobb (1912).
During the First World War Flagg designed 46 art, prints and posters for the government. This included the famous Uncle Sam poster with the caption "I Want You for the U.S. Army”. An adapted version of this poster was also used during the Second World War. James Montgomery Flagg died in 1960.