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James Montgomery Flagg Drawings and Watercolor Paintings

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
As Easy as Kiss Me Hand
By James Montgomery Flagg
Located in Fort Washington, PA
Signed Lower Right
Category

20th Century James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Paper, Watercolor

Mr. Bingle
By James Montgomery Flagg
Located in Fort Washington, PA
Signed Lower Left "Mr. Bingle." Frontispiece illustration for "Mr. Bingle" by George Barr McCutcheon (New York: Dodd, Mead and Co., 1915.)
Category

1910s James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Ink, Board, Pen

"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 Drawings and Watercolor Paintings

Materials

Paper, Watercolor, 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 Drawings and Watercolor Paintings

Materials

Crayon, Pencil

“Three-Fingered Jenny, ” story illustration for McClure’s
By James Montgomery Flagg
Located in Fort Washington, PA
Story illustration for “Three-Fingered Jenny” by C.N. and A.M. Williamson (Alice Muriel Williamson) for McClure’s Magazine, published February 1916, page 24. The full caption reads...
Category

20th Century James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Ink, Board

“She struggled until she heard him telling her to be quiet.”
By James Montgomery Flagg
Located in Fort Washington, PA
Story illustration for “Tin Crown” by Rex Beach for Cosmopolitan, published February 1933, page 61. Battling writer's block, songwriter Bertram Berry relies on the hidden talents of...
Category

20th Century Romantic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Board, Pencil, Watercolor

Cream of Wheat Ad
By James Montgomery Flagg
Located in Fort Washington, PA
Signed Lower Left
Category

1910s James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Watercolor, Board

Setting Off
By James Montgomery Flagg
Located in Fort Washington, PA
Medium: Ink on Paperboard Dimensions: 24.50" x 21.00" Signature: Signed 'James Montgomery Flagg' Lower Left
Category

20th Century James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Paper, Ink, Board

The Working Man s Choice
By James Montgomery Flagg
Located in Fort Washington, PA
Medium: Pen and Ink on Paper Signature: Inscribed and Signed
Category

1920s James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Paper, Ink, Pen

Dancing with Woman Overlooking
By James Montgomery Flagg
Located in Fort Washington, PA
Contact for exact dimensions.
Category

20th Century James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Pen

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Previously Available Items
Uncle Sam
By James Montgomery Flagg
Located in Fort Washington, PA
Medium: Pen and Ink on Paper Signature: Signed and Dated Lower Left Signed, dedicated and dated lower left. "To Ruth Bryan Owen, Jan 14th, 1931". Image of Uncle Sam...
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Street Scene with Lion
By James Montgomery Flagg
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20th Century James Montgomery Flagg Drawings and Watercolor Paintings

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Man Showing Young Boy a Toy Boat
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Three Women
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20th Century James Montgomery Flagg Drawings and Watercolor Paintings

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"I Do Fearfully Put in a Shallow Water"
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James Montgomery Flagg drawings and watercolor paintings for sale on 1stDibs.

Find a wide variety of authentic James Montgomery Flagg drawings and watercolor paintings available for sale on 1stDibs. You can also browse by medium to find art by James Montgomery Flagg in ink, paper, pen and more. Not every interior allows for large James Montgomery Flagg drawings and watercolor paintings, so small editions measuring 1 inch across are available. Customers who are interested in this artist might also find the work of Louise Laplante, Seth Clark, and William Sommer. James Montgomery Flagg drawings and watercolor paintings prices can differ depending upon medium, time period and other attributes. On 1stDibs, the price for these items starts at $1,200 and tops out at $16,000, while the average work can sell for $3,900.

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