From Jeeves to Uncle Sam : The Legacy of James Montgomery Flagg

James Montgomery Flagg, one of the most versatile artists of the early-mid twentieth century, would have been 137 today.  He was born in suburban Pelham Manor, New York (approximately 14 miles northeast of Manhattan) but was always interested in drawing urban life.


Sunday Magazine, December 18, 1910

By age 12, Flagg had sold his first illustration for $10 to St. Nicholas magazine. By age 14, he had become a regular staff member for Life, and two years later, was also on the staff of Life‘s rival,Judge.


Judge, November 27, 1920

Flagg was skilled at using many mediums, including watercolors, oils, pastels, charcoal, and pencil.  A great amount of his work is in pen-and-ink.  Flagg seldom used cross-hatching, which was the common technique used with pen-and-ink.  Instead, he used carefully selected parallel lines to create his effects.

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Collier’s, April 25, 1931

Flagg believed that when creating fiction illustrations, the artist needed to truly understand the story and its characters before attempting to illustrate them.  He stated “Good illustrating is far more than depicting a bit of action as described by the author.”

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Part 6 of the 8-part novella Double Indemnity, Liberty, 1936

For assignments for Cosmopolitan, Flagg illustrated the P.G. Wodehouse stories of English aristocrat Bertie Wooster and his talented valet, Jeeves.  Flagg’s depiction of Jeeves would become the prototype for that character.

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Wooster and Jeeves, from Cosmopolitan, January 1934

The character prototype that Flagg is best remembered for is his depiction of Uncle Sam.  According to legend, the Uncle Sam character started being used during the War of 1812, although was mentioned in original lyrics to Yankee Doodle during the Revolutionary War.  Uncle Sam had always been depicted as a congenial, folksy, older man, but Flagg’s stern and muscular version forever changed the way the character would be viewed.

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Judge, June 8, 1918

Flagg’s Uncle Sam originally started out as a July 1916 cover for Leslie‘s magazine. The magazine had wanted it for a 1914 cover, but Flagg kept refusing the assignment.  There are differing accounts as to whom Flagg used as a model.  According to Flagg’s granddaughter, the artist found the perfect model one day riding on a train, which made him finally agree to draw the cover.  However, by the time World War II began, Flagg was resembling his own creation and decided to use himself as the model to save on model fees.

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U.S. Army and U.S. Air Force recruiting advertisement, Collier’s, September 11, 1948

During World War I, Flagg was one of artists in the Division of Pictorial Publicty, to which the U.S. government sent requests for war propaganda and recruitment material.  The government asked Flagg to use his Uncle Sam for an Army recruitment poster.  The “I Want You” poster is one of the most recognizable war posters of all time, with 350,000 copies printed during World War I and approximately 400,000 copies printed during World War II.  This is the work for which Flagg is most remembered.

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U.S. Army recruitment poster, 1917

Uncle Sam made his appearance on numerous posters for the war effort, including recruitment, war stamps purchases, and morale building.  Flagg also designed dramatic, eye-catching propaganda and recruitment posters without the iconic character.  He designed 46 posters in all.

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U.S. Navy recruitment poster, 1917

Flagg studied at various art schools for six “wasted” years, since he never felt the education assisted his artistic development.  He ended up believing that artists were born to be artist and that art could not be taught.  At one point, during his studies in London, he thought he wanted to be a portrait painter, but decided to return to illustration since there was more subject material.

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Sunday Magazine, February 7, 1915

One of Flagg’s favorite subjects was women.  During the 1920s, Flagg was creating women with curves, which was against the trend of the time.  His image of his ideal woman never changed throughout the years.

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Judge, September 15, 1923

As magazines began to use more photography and more modern-style art, Flagg’s style of illustration was no longer in demand.  Flagg died three weeks before his 83rd birthday after living to see his career fade into obscurity.

James Montgomery Flagg’s legacy can still be seen through several collections at Modern Graphic History Library:

Information on Flagg’s life came from:

James Montgomery Flagg. Sparticus Educational, n.d.

Meyer, Susan E. America’s Great Illustrators. Galahad Books, 1987.

Reed, Walt. The Illustrator In America, 1860-2000. Society of Illustrators, 2001.

Steward, Nicholas. James Montgomery Flagg: Uncle Sam and Beyond. Collectors Press, 1997.

Uncle Sam. Wikipedia, n.d.

About the author

Andrea Degener is the Visual Materials Processing Archivist in the department of Special Collections at Washington University Libraries.