James Montgomery Flagg (Monty to his friends) was born June 18, 1877. He grew up in Brooklyn and Manhattan and began working in the editorial offices of St. Nicholas, Judge and Life, ready markets for his humorous drawings. The Art Students League offered more stimulating company than high school so he studied there for four years while he still sold his work to the weeklies.
Following his marriage to Nellie McCormick, and with Life magazine’s support, Flagg studied with Victor Marec in Paris. Flagg’s studio portraits were exhibited in the salon shows. He and his wife returned to New York in 1904 to an apartment in the Hotel des Artistes. While he was adept at many media-including watercolor, oils and sculpture-he preferred the pen over all. Harper’s Weekly, The Saturday Evening Post, Liberty, McClure’s, Century, Good Housekeeping and Scribner’s all helped to push Flagg’s earnings to the top of his profession.
When America entered into WWI, illustrators rallied around the banner of Charles Dana Gibson’s Division of Pictorial Publicity. Flagg, who had already created the “I Want You” image for Leslie’s Weekly, proceeded to design 46 posters for the war effort. During WWII, Flagg’s Uncle Sam reemerged and could be found in front of every post office and recruiting station across the country. The period between these wars found James Montgomery Flagg at a social pinnacle. He had moved his studio to 57th Street and summered in Maine. He took this leisure with the Barrymores, the Roosevelts, the fellows of his many clubs and a long list of Hollywood starlets.
Flagg was a character “both loved and hated with equal fierceness.” He detested sham and pretense. His retorts caught the unwary off-guard and hardened his friends. In Flagg’s later years, when his failing eyesight forced him to abandon his art, he often took out his frustrations on his friends and himself. He died in 1960 at age 82. Everett Raymond Kinstler said of Monty: “Everything he did was as uniquely Flagg as his manner of speaking or his eyebrows. He loved beauty and he loved laughter.” It is unlikely that we will see another James Montgomery Flagg.