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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
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

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

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

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 Drawings and Watercolor Paintings

Materials

Ink, Pen, Paper

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

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

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

A Struggle
By James Montgomery Flagg
Located in Fort Washington, PA
Medium: Watercolor and Pencil on Board Signature: Signed Lower Left James Montgomery Flagg lived with gusto. He epitomized the public concept of the handsome, bohemian artist, su...
Category

20th Century Romantic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Watercolor, Board, 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 Drawings and Watercolor Paintings

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 Drawings and Watercolor Paintings

Materials

Paper, Ink, Board

Related Items
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Located in PARIS, FR
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He is said to have been a pupil of Francesco Francia (1450 - 1517) and his name appears for the first time in 1511 in a contract with the painter Bagnacavallo (c. 1484 - 1542) for the frescoes of a church in Faenza. He then collaborated with Girolamo da Carpi, at San Michele in Bosco and at the villa of Belriguardo. He must have gone to Rome for the first time with Bagnacavallo between 1511 and 1519. There he discovered the art of Raphael, with whom he might have worked, and that of Polidoro da Caravaggio. This first visit, and those that followed, were the occasion for an intense study of ancient and modern art, as illustrated by his abundant graphic production. Polidoro da Caravaggio had a particular influence on the technique adopted by Pupini. Executed on coloured paper, his drawings generally combine pen, brown ink and wash with abundant highlights of white gouache, as in the drawing presented here. 2. The Abduction of the Sabine Women Our drawing is an adaptation of a fresco painted between 1525 and 1527 by Polidoro da Caravaggio on the façade of the Milesi Palace in Rome. These painted façades were very famous from the moment they were painted and inspired many artists during their stay in Rome. These frescoes are now very deteriorated and difficult to see, as the palace is in a rather narrow street. The episode of the abduction of the Sabine women (which appears in the centre of the photo above) is a historical theme that goes back to the origins of Rome and is recounted both by Titus Livius (Ab Urbe condita I,13), by Ovid (Fasti III, 199-228) and by Plutarch (II, Romulus 14-19). After killing his twin brother Romus, Romulus populates the city of Rome by opening it up to refugees and brigands and finds himself with an excess of men. Because of their reputation, none of the inhabitants of the neighbouring cities want to give them their daughters in marriage. 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16th Century Old Masters James Montgomery Flagg Drawings and Watercolor Paintings

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“Sleigh Ride”
Located in Southampton, NY
Original artwork for Manville Card Company. Circa 1975. Condition is very good. Watercolor and gouache on heavy card stock. Will be sold with original Christmas card with notations. Sheet size 9 by 10...
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1970s Other Art Style James Montgomery Flagg Drawings and Watercolor Paintings

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Watercolor, Gouache, Cardboard

“Sleigh Ride”
“Sleigh Ride”
No Reserve
H 7.5 in W 9 in D 0.25 in
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Materials

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Located in Southampton, NY
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Category

1960s Other Art Style James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Watercolor, Gouache, Cardboard

“The Caroler’s”
“The Caroler’s”
No Reserve
H 10 in W 5 in D 0.25 in
Hank Aaron, Ted Williams, Stan Musial, Willie Mays, Baseball All-Stars Painting
By Margie Lawrence
Located in Chicago, IL
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2010s Contemporary James Montgomery Flagg Drawings and Watercolor Paintings

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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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1930s James Montgomery Flagg Drawings and Watercolor Paintings

Materials

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 Drawings and Watercolor Paintings

Materials

Pen

Man Showing Young Boy a Toy Boat
By James Montgomery Flagg
Located in Fort Washington, PA
Medium: Pen and Ink on Paper Signature: Signed Lower Right Man Showing Young Boy a Toy Boat
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20th Century James Montgomery Flagg Drawings and Watercolor Paintings

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Paper, Ink, Pen

The Woman's Decision
By James Montgomery Flagg
Located in New Orleans, LA
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 Drawings and Watercolor Paintings

Materials

Paper, Watercolor

"I Do Fearfully Put in a Shallow Water"
By James Montgomery Flagg
Located in Fort Washington, PA
Signed Lower Right
Category

20th Century James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Ink, Board

Young Woman Contemplates Her Future: Romance vs. Money
By James Montgomery Flagg
Located in Fort Washington, PA
James Montgomery Flagg lived with gusto. He epitomized the public concept of the handsome, bohemian artist, surrounded by beautiful models, dashing off pictures with sheer exuber...
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1910s Other Art Style James Montgomery Flagg Drawings and Watercolor Paintings

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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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