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“Monty” was born with moxie. The date was June 18, 1877. Elisha and Anna’s son 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. By 16, he was a regular contributor to the weeklies. 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.

In 1898, a year after he left the League, Flagg, and Richard Kimbrough, a fellow League student, left for England, where they studied at Herkomer’s Art School in Bushley and drew the Americans abroad. Flagg’s “Yankee Girls” was published soon afterward by an English firm. This was the first step in the development of the “Flagg Girl.” Kimbrough’s untimely death ended their holiday and Flagg returned home.

The suddenness of Flagg’s marriage to St. Louis socialite, Nellie McCormick, in 1899 has never been fully explained. Years his senior and raised in a loftier stratum, she appeared less wife than patron. For four years, Flagg and his wife traveled throughout the U.S. and Europe. 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 off Central Park West.

It was at this West 67th Street studio that illustrations rolled off his board at the rate of one per day. 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. He illustrated Jeeves by P.G. Wodehouse in Collier’s for many years.

Flagg’s illustrations were held in high esteem by such top writers of the day as Edna Ferber, W.S. Hart, Julian Street, Booth Tarkington, Sinclair Lewis and George Barr McCutcheon. Flagg’s favorite writer, though, was himself. His writings exhibited a witty sense of the ridiculous as he poked fun at nearly every established convention; Nervy Nat (a Judge series), satirical short stories, screenplays, the Dutch Treat Club’s annual presentation and the Society of Illustrators’ smokers and girlie shows were a few of Flagg’s literary forums. During one period, he found time to write 24 short screenplays, a weekly syndicated column and a Broadway play.

When America entered into World War I, 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 World War II, 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. Harper’s magazine wrote of him: “although his industry appears appalling, he does not lack an abundance of leisure.” He took this leisure with the Barrymores, the Roosevelts, the fellows of his many clubs and a long list of Hollywood starlets. They were honored to be the brunt of a Flagg comment or the subject of a humorous or serious portrait. Rosalind Russell said of hers, “You certainly can paint, you old bastard!”

The period between the wars also found Flagg’s personal life in turmoil. Nellie died in 1923 and he married Dorothy Wadman the following year. The second Mrs. Flagg, who was the mother of his only child, Faith, suffered a nervous collapse and was hospitalized for the rest of her life. He never remarried.

J.M. Flagg was 48 years old at the time of his daughter’s birth. His lifestyle was not perfectly suited to raise a child but as a single parent, he did his best. Flagg adored Faith and she was a frequent model for him as she grew through the years. His portraits of her record a softer side of Flagg’s personality.

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. “I’ve always been more interested in battling life today, than in trying to build a dead tomorrow.” After two heart attacks, near blindness, Monty died in 1960 at age 82. Dean Cornwell, Arthur William Brown, Jack Dempsey and Flagg’s close friend, Everett Raymond Kinstler were among those at the funeral. 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.” He told me, “If the cerulean brass hats ever send me to heaven, and I find no laughter, I will get the Hell out of there.” It is unlikely that we will see another James Montgomery Flagg.

© 2011 Society of Illustrators

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