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

1910s James Montgomery Flagg Figurative Drawings and Watercolors

Materials

Watercolor, Board

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 Figurative Drawings and Watercolors

Materials

Ink, Board, Pen

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

20th Century James Montgomery Flagg Figurative Drawings and Watercolors

Materials

Pen

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 Figurative Drawings and Watercolors

Materials

Paper, Ink, Pen

Three Women
By James Montgomery Flagg
Located in Fort Washington, PA
Medium: Pen and Ink on Paper Signature: Signed Lower Right Pencil notation, "Same Focus", "Live on Coffee"
Category

20th Century James Montgomery Flagg Figurative Drawings and Watercolors

Materials

Ink, Pen, Paper

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

20th Century James Montgomery Flagg Figurative Drawings and Watercolors

Materials

Paper, Watercolor

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 Figurative Drawings and Watercolors

Materials

Crayon, Pencil

"Three Fingered Jerry", McClure's Magazine
By James Montgomery Flagg
Located in Fort Washington, PA
Signed Lower Right
Category

20th Century James Montgomery Flagg Figurative Drawings and Watercolors

Materials

Ink, 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 Figurative Drawings and Watercolors

Materials

Paper, Ink, Board

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Early life Willing was born in Brooklyn on March 28, 1888 to John Thomson Willing (August 4, 1860 – July 8, 1947)[1][2] and Charlotte Elizabeth Van Der Veer Willing (December 1, 1859 – March 4, 1930).[3] Thomson Willing was a noted illustrator and art editor. He was also well known for finding new artistic talent. Jessie Willing was the eldest of three children. Her brother Van Der Veer (November 30, 1889 – January 14, 1919), who died of pneumonia at the age of 29, was an advertising agent.[4] Her sister Elizabeth Hunnewell Willing (July 26, 1908 – August 15, 1991) was one of the first women to graduate from the Philadelphia Divinity School.[5][6] Elizabeth married the Rev. Orrin Judd, rector of St. Mary's Episcopal Church, on September 22, 1931, and was active in church work.[citation needed] The Willing family moved to the Germantown neighborhood of Philadelphia in 1901 or 1902. Jessie Willing attended the Stevens School, from which she graduated in 1905. 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Original Painting Cathedral Interior New Yorker Cover Proposal 1939 Jesus Church
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Mother and Child - Drawing - 1962
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Category

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The Flight into Egypt
Located in New York, NY
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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...
Category

1930s James Montgomery Flagg Figurative Drawings and Watercolors

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Ink, Paper, Pen

Street Scene with Lion
By James Montgomery Flagg
Located in Fort Washington, PA
Contact for exact dimensions.
Category

20th Century James Montgomery Flagg Figurative Drawings and Watercolors

Materials

Pen

The Woman's Decision
By James Montgomery Flagg
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A woman must decide between a career or love in this watercolor by the great American illustrator James Montgomery Flagg. At the time of this painting's creation, a woman's place in ...
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Early 20th Century Other Art Style James Montgomery Flagg Figurative Drawings and Watercolors

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"I Do Fearfully Put in a Shallow Water"
By James Montgomery Flagg
Located in Fort Washington, PA
Signed Lower Right
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20th Century James Montgomery Flagg Figurative Drawings and Watercolors

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Ink, Board

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

Find a wide variety of authentic James Montgomery Flagg figurative drawings and watercolors available for sale on 1stDibs. You can also browse by medium to find art by James Montgomery Flagg in ink, pen, paper and more. Not every interior allows for large James Montgomery Flagg figurative drawings and watercolors, so small editions measuring 1 inch across are available. Customers who are interested in this artist might also find the work of Louise Laplante, Keith Carrington, and Kyle Andrew Szpyrka. James Montgomery Flagg figurative drawings and watercolors 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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