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James Montgomery Flagg Portrait Drawings and Watercolors

American, 1877-1960

James Montgomery Flagg was a prodigious illustrator, working as a contributing artist to Life magazine at the surprisingly young age of 14. Flagg was born on June 18, 1877, in the Village of Pelham. He is most famous for creating the first image of the fictional Uncle Sam. His ‘I Want You’ lithographed image of Uncle Sam was published in 1917, during the First World War. It is storied that Flagg used his own image as the model for Uncle Sam, imagining himself as a much older man and with facial hair. Flagg died on May 27, 1960, in New York.

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Artist: James Montgomery Flagg
"I Should Worry, " Cover for Judge Magazine, Feb. 28, 1914
By James Montgomery Flagg
Located in Fort Washington, PA
Medium: Watercolor and Gouache with Graphite on Paper Mounted Signature: Signed Lower Right "I Should Worry." Cover illustration for Judge magazine, pu...
Category

1910s James Montgomery Flagg Portrait Drawings and Watercolors

Materials

Watercolor, Paper, Gouache, Graphite

Actress June Knight
By James Montgomery Flagg
Located in Miami, FL
Celebrity portrait sketch of actress June Knight but James Montgomery Flagg on card stock in two colors. Signed and inscribed lower right. The work is unframed. There is a slight cr...
Category

1930s Academic James Montgomery Flagg Portrait Drawings and Watercolors

Materials

Pencil, Crayon

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James Montgomery Flagg portrait drawings and watercolors for sale on 1stDibs.

Find a wide variety of authentic James Montgomery Flagg portrait drawings and watercolors available for sale on 1stDibs. You can also browse by medium to find art by James Montgomery Flagg in pencil, crayon, gouache and more. Not every interior allows for large James Montgomery Flagg portrait drawings and watercolors, so small editions measuring 8 inches across are available. James Montgomery Flagg portrait drawings and watercolors prices can differ depending upon medium, time period and other attributes. On 1stDibs, the price for these items starts at $1,900 and tops out at $13,500, while the average work can sell for $7,700.

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