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| Flagg as Captain Kidd at the Illustrators' Ball, a masquerade ball in New York in 1917 |
James Montgomery Flagg 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.
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.”
© 2011 Society of Illustrators
This is part 1 of a 5-part series on the works of James Montgomery Flagg:
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| 1893-1924 Y.W.C.A. Jubilee Pageant colour lithograph poster |
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| 1893-1924 The Bookman, April two-colour lithograph poster |
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| 1893-1924 Hart Schaffner & Marx colour lithograph poster |
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| 1893-95 Atlantic: August lithograph poster 41.6 x 31.4 cm |
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| 1895 The Art of Living by Robert Grant colour lithograph poster |
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| 1897 Illustration for "A Magician for One Day" by Tudor Jenks published in St. Nicholas Illustrated magazine, October 1897 ink and watercolour on paper. 35.5 x 50.8 cm |
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| 1897 Illustration for "A Magician for One Day" by Tudor Jenks published in St. Nicholas Illustrated magazine, October 1897 ink and watercolour on paper. 35.5 x 50.8 cm |
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| 1898 Illustration for "Johnny and the Giant" by J. Rowe Webster published in St. Nicholas Illustrated magazine, January 1898 ink & watercolour on paper 50.8 x 35.5 cm |
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| 1898 Illustration for "Johnny and the Giant" by J. Rowe Webster published in St. Nicholas Illustrated magazine, January 1898 ink & watercolour on paper 50.8 x 35.5 cm |
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| 1898 Illustration for "Johnny and the Giant" by J. Rowe Webster published in St. Nicholas Illustrated magazine, January 1898 ink & watercolour on paper 50.8 x 35.5 cm |
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1898-12 John Fiske's Old Virginia Atlantic: December two-colour lithograph poster |
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| 1900-20 Study of a Woman oil on panel 59.1 x 39.1 |
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| 1902 Thalia Westcott (Mrs. Stephen Caldwell Millett) oil on canvas 126.5 x 91 cm |
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| 1905 Scribner's Fiction Number colour lithograph 60.25 x 40 cm |
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| 1905 Life magazine cover, March 23 1905 A map of the world (As seen by him.) |
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| 1905 Judge magazine cover, Christmas 1905 edition |
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| 1906 Stung! |
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| 1906 Leslie's Weekly, April 26 |
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| 1907 The Violin Maker’s Village watercolour on board 58.4 x 43.2 cm |
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| 1907 "Now be good" Life magazine 19 December 1907 |
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| 1908 The Prodigal, Everbody's Magazine pencil, pen and ink on board 55.2 x 74.9 cm |
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| 1908 Life magazine cover Travel Number June 4 1908 |
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| 1908 Life magazine cover The World: Good versus Evil |
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| 1908 Cream of Wheat is Ready colour lithograph advertisement |
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| "The enraged captive .. turned round, his face ablaze with anger." |
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| "The three men were filled with consternation." |
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| "We're both blooming prisoners, that's what we are!" |
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| "You miss a great deal of pleasure in life." |
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| 1909 Bill Truetell by George H. Brennan two-colour lithograph poster |
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| 1909 Life magazine cover Travel Number January 21 1909 |
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| 1909 Life magazine cover Valentine Number February1909 |
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| 1909 Life magazine cover Liar's Number, February 18 1909 |
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| 1909 Life magazine cover St. Patrick's Day number, March 18 1909 |
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| 1909 Life magazine cover Jungle number, April 15 1909 |
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| 1909 Life magazine cover Garden number, June 24 1909 |
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| 1909 Life magazine cover Etiquette Number, September 1909 |
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| 1909 Life magazine cover Thanksgiving number, November 4 |
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| 1909 Life magazine cover Christmas number, December 23 1909 |
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| 1909 The Modern Pegasus The fictional bartender Mr. Dooley viewing the modern Pegasus published in The American Magazine |
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| 1909 The American Suffragettes |
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| 1909 Sunday Magazine of the Boston Sunday Post August 1. 1909 issue |
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| 1909 She sailed majestically past the wretch, followed meekly by Septimus ink on paper 73.6 x 55.8 cm |
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