Skip to main content

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.

to
2
3
5
Overall Width
to
Overall Height
to
10
3
1
1
5
3
2
10
8
6
5
4
3
1
1
1
1
1
5
4
4
4
4
25
808
408
306
282
6
10
Artist: James Montgomery Flagg
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

"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

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

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

Board, Pencil, Watercolor

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

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

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

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

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

"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

Related Items
French School 19th Century, A Muskeeter, original pencil drawing
Located in Paris, FR
French school 19th Century A Muskeeter Pencil on paper 26.5 x 17 cm Bears a signature "F. Roybet" in the lower right In quite good condition, bears some visible foxings, In an old mount (some damages) (not framed) Even if the style, execution and of course subject are those of Ferdinand Roybet...
Category

1890s Academic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Carbon Pencil

Fernand de Launay (1855-1904) Portrait of a child, 1890, original drawing
By Fernand de Launay
Located in Paris, FR
Fernand de Launay (1838-1904) Portrait of a child, probably the daughter of the artist Lead pencil on paper Signed and dated "4 septembre 1890" on the lower left 27 x 21 cm In quite ...
Category

1890s Academic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Carbon Pencil

"Self Portrait Conte Sketch" rare Ben Fenske work on paper - academic study
By Ben Fenske
Located in Sag Harbor, NY
A colorful self-portrait from Ben Fenske, staring at the viewer straight-on. Hues of red dominate. Unframed. Ben Fenske (b. 1978) although a native of Minnesota, and has been worki...
Category

Early 2000s Academic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Paper, Conté

Self Portrait Sketch
By Ben Fenske
Located in Sag Harbor, NY
An early work on paper, by American Impressionist painter, Ben Fenske. It's rare to see a drawing like this from Fenske, especially of a self portrait. Fenske uses classical draftin...
Category

Early 2000s Academic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Paper, Conté

Romantic Landscape of Scandinavian Enchanted Forest, Large Lake Print Cyanotype
By Kind of Cyan
Located in Barcelona, ES
This is an exclusive handprinted limited edition cyanotype. Lovely scene of a hidden pond in a Scandinavian forest. Details: + Title: Scandinavian Enchanted Forest + Year: 2024 + ...
Category

2010s Romantic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Photographic Film, Emulsion, Watercolor, Photographic Paper, C Print, Co...

Ecole de Paris Mid 20th Century: Wartime Figures
By Henri Miloch
Located in Cirencester, Gloucestershire
Paris: A Wartime Study of Figures Relaxing in Springtime by Henri Miloch (1898-1979) Unsigned watercolour, graphite and gouache painting on artist's paper, unframed Sheet: 12.25 x 9...
Category

1940s Impressionist James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Watercolor, Gouache, Graphite

France 19th century, The Bohème artist in his workshop, watercolor
Located in Paris, FR
France circa 1850 The Bohème artist in his workshop Watercolor on paper 15.5 x 21.5 cm In good condition except a small tear (visible on the photographs) on the upper right border. I...
Category

1840s Romantic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Watercolor

Church Interior
By Ray Quigley
Located in Buffalo, NY
A modern illustration by American artist Ray Quigley depicting two men inside of a church.
Category

1950s Realist James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Gouache, Illustration Board, Ink

'Stonehenge at Sunset', Royal Academy, RSBA, Benezit, Wiltshire, Druid, Celtic
By Robert Gallon
Located in Santa Cruz, CA
Signed lower left, 'R. Gallon' for Robert Gallon (English, 1845-1925) and painted circa 1880. This well-listed landscape and seascape painter maintained a studio in St John's Wood, ...
Category

Late 19th Century Romantic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Watercolor, Illustration Board

French School 19th Century, Portrait of a dandy, watercolor on paper
Located in Paris, FR
French School 19th Century, Portrait of a dandy, watercolor on paper 19 x 13 cm Signed (?) with pencil lower right "L ... " illegible Framed : 29 x 23 cm
Category

1880s Romantic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Watercolor

Auguste Mayer (1805-1890) A seascape with a boat, signed drawing
Located in Paris, FR
Auguste Mayer (1803-1890 A seascape with a boat signed with the initials on the lower left Pencil and heightenings of white gouache on paper 17.5 x 26 cm...
Category

1860s Romantic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Gouache, Carbon Pencil

Edouard Detaille (1848 1912) Soldiers, a study, ink on wood
By Jean Baptiste Édouard Detaille
Located in Paris, FR
Edouard Detaille (1848-1912) Soldiers, a study Black ink on a wood panel 12.5 x 13 cm Framed : 20 x 20.5 cm On the back of the panel a label inscribed "Dessin à la plume par Detaill...
Category

1880s Academic James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Ink

Previously Available Items
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

Paper, Ink, Pen

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 Drawings and Watercolor Paintings

Materials

Paper, Ink, 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
Category

20th Century James Montgomery Flagg Drawings and Watercolor Paintings

Materials

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 ...
Category

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...
Category

1910s Other Art Style James Montgomery Flagg Drawings and Watercolor Paintings

Materials

Paper, Watercolor

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.

Recently Viewed

View All