James Montgomery Flagg (1877-1960) was born in Pelham Manor, New York. Flagg always had a passion for drawing and even had his illustrations picked up by national magazines when he was 12 years old. He was a contributing artist to Life magazine by the age of 14, and then joined the staff of Judge magazine by 15. In 1898 he began attending the Art Students League of New York, and went on to study the fine arts in London and Paris from 1898-1900.

When he returned to the U.S. he created illustrations for every medium ranging from books to advertising to spot drawings. He created the comic strip Nervy Nat that would appear in Judge magazine from 1903 to 1907. His most famous art piece is a poster featuring Uncle Sam with the words “I Want YOU for U.S. Army.” The poster was meant to encourage enlistment into the United States Army during World War l. The poster was printed over four million times during World War l, and a revised version was used again during World War ll.

Flagg was purportedly the highest paid magazine illustrator in America during his prime. He worked for both The Saturday Evening Post and Collier’s. His autobiography, Roses and Buckshot, was published in 1946. He painted portraits as well. Some of his most famous sitters were Mark Twain and Jack Dempsey.

He created one cover for The Saturday Evening Post.