Skip to main content

James Montgomery Flagg 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
1
2
Overall Width
to
Overall Height
to
3
2
1
3
3
3
2
2
3
2
2
1
1
25
779
726
723
683
2
1
3
Artist: James Montgomery Flagg
The Big Accusation
By James Montgomery Flagg
Located in Fort Washington, PA
Medium: Pen and Ink on Paper Signature: Signed Lower Left James Montgomery Flagg lived with gusto. He epitomized the public concept of the handsome, bohemian artist, surrounded ...
Category

20th Century Other Art Style James Montgomery Flagg Paintings

Materials

Ink, Paper, Pen

The Discussion
By James Montgomery Flagg
Located in Fort Washington, PA
Medium: Ink on Board Signature: Signed and Inscribed Lower Left James Montgomery Flagg lived with gusto. He epitomized the public concept of the handsome, bohemian artist, surro...
Category

20th Century Other Art Style James Montgomery Flagg Paintings

Materials

Board, Ink

“Slumming Among the Four Hundred, ” Post Illustration
By James Montgomery Flagg
Located in Fort Washington, PA
Original illustration for the article “Slumming Among the Four Hundred” by Alfred Henry Lewis, for The Saturday Evening Post, published November 2, 1907. The article offers a satiri...
Category

20th Century Romantic James Montgomery Flagg Paintings

Materials

Board, Ink, Paper, Pencil

Related Items
Signed Feminist LGBTQ+ Acrylic on Board Painting - Practice Makes Perfect 120
Located in New York, NY
Linda Stein, Practice Makes Perfect 120 - Signed Feminist LGBTQ+ Colorful Acrylic on Board Painting Practice Makes Perfect 120 is from Linda Stein's Missives series--a body of work...
Category

1970s Feminist James Montgomery Flagg Paintings

Materials

Acrylic, Board, Ink, Laid Paper

Horse, Drawing, Ink on Paper, Black, Grey by Indian Artist Sunil Das "In Stock"
By Sunil Das
Located in Kolkata, West Bengal
Sunil Das - Horse - 8 x 5 inches (unframed size) Ink on Paper ( Unframed & Delivered ) Sunil Das was one of India's most important postmodernist painters and rose to prominence thro...
Category

2010s Modern James Montgomery Flagg Paintings

Materials

Paper, Ink, Pen

Woman Playing with a Kitten
Located in Sheffield, MA
Willem Steelink Jr. Dutch, 1856-1928 Woman Playing with a Kitten Oil on board 9 ¾ X 7 ¾ in. w/ frame 13 ¾ X 11 ¾ in. Signed "Wilm. Steelink" upper right Willem Steelink Jr. (16 Jul...
Category

Late 19th Century Romantic James Montgomery Flagg Paintings

Materials

Oil, Board

Poppy and Anemone Still Life Floral Study in Oil on Linen
By Karl Harald Alfred Broge
Located in Soquel, CA
Delicate and detailed floral still life by Alfred Broge (Danish, 1870-1955). Three white anemones and one pink poppy, all with stems and leaves, sit against a medium grey background...
Category

Early 1900s Romantic James Montgomery Flagg Paintings

Materials

Linen, Oil, Board

Ruins of the Theatre at Taormina, Sicily
Located in Stockholm, SE
Artist Unknown, Second Quarter Nineteenth Century Ruins of the Theatre at Taormina, Sicily oil on board, partially arched top unframed: 26 x 36.5 cm (10 1/4 x 14 3/8 in) framed: 31...
Category

Late 19th Century Romantic James Montgomery Flagg Paintings

Materials

Oil, Board

Antique 19th Century Marine Seascape Coastal Maritime English Channel Painting
By James Webb
Located in Portland, OR
A good antique marine oil painting by James Webb (1825-1895), circa 1860, ex-Sothebys. The painting depicts a stormy or squally sea, most likely the English channel, the rocky cliff...
Category

Mid-19th Century Romantic James Montgomery Flagg Paintings

Materials

Oil, Board

Miniature 19th Century Austrian Pastoral Oil on Wood
Located in Soquel, CA
Original Miniature 19th Century Austrian Pastoral Figurative Oil Painting on Wood Painted in the manner of late Romanticism, this charming miniature pastoral landscape by Edmund Fri...
Category

1870s Romantic James Montgomery Flagg Paintings

Materials

Gesso, Oil, Board

"Landscape Painting"
Located in Edinburgh, GB
19th-Century Landscape Painting – Pastoral River Scene Artist: Unidentified Medium: Oil on Board Dimensions: Framed: 35 x 47 cm Artwork: 25 x 38 cm Style: Romanticism / Pastoral Lan...
Category

19th Century Romantic James Montgomery Flagg Paintings

Materials

Oil, Board

Lost in Her Thoughts, 1890-1892, by Pinckney Marcius-Simons, French Romanticism
Located in Grand Rapids, MI
Pinckney Marcius-Simons, (American, French, 1867-1909) Signed: Marcius-Simons, (lower, right) " Lost in Her Thoughts ", circa 1890-1892 Oil on mahogany panel bearing the stamp on verso of " H. Vieille e. Troisgros Sueei, 55 Rue de Laval...
Category

19th Century Romantic James Montgomery Flagg Paintings

Materials

Oil, Board

Christ Falls on the Way to Calvary, Dutch-Italianate School, c.18th-19th Cent.
Located in Soquel, CA
Expressive depiction of Christ being aided by Simon of Cyrene by an unknown artist, Italiante School style of 17th-century Northern European painters principally Dutch, c.1700s-1800s. This piece is composed of oil on linen, laid down on fiberboard. Presented in a giltwood frame. Image size: 42"H x 33"W. Italianate painters, group of 17th-century northern European painters, principally Dutch, who traveled in Italy and, consciously adopting the style of landscape painting that they found there, incorporated Italian models and motifs into their own works. Chief among the Italianates were Bartholomeus Breenbergh, Andries and Jan Both, Nicolaes Berchem, and Jan Asselijn...
Category

18th Century Romantic James Montgomery Flagg Paintings

Materials

Linen, Oil, Fiberboard

Australian Gum Trees Landscape
By John Sharman (b.1947)
Located in Soquel, CA
Beautiful landscape of gum trees by listed Australian artist John Sharman (Australian, b. 1947), c.1990. These lovely iconic trees appear in the foreground, while the Australian landscape sprawls out into the distance. Signed "John Sharman" lower right. Displayed in a silver tone giltwood frame. Image size, 21"H x 23"L. Born in Sydney in 1947, John Sharman turned to full time professional art practice in 1980. He became part of a group of artists that included Bob Simpson, Doug Sealy, Robert Wilson, Warwick Fuller...
Category

1980s Romantic James Montgomery Flagg Paintings

Materials

Canvas, Oil, Cardboard

“The Showman” after Abraham Le Blond
Located in San Francisco, CA
This itinerant showman, with his drum and what appears to be a peep show, met a real need. What’s offered definitely engages the man in the group, but the woman pawing at his shoulde...
Category

19th Century Romantic James Montgomery Flagg Paintings

Materials

Oil, Board

“The Showman” after Abraham Le Blond
“The Showman” after Abraham Le Blond
$650
H 9.5 in W 11 in D 1.5 in
Previously Available Items
Portrait of F. Scott Fitzgerald napping
By James Montgomery Flagg
Located in Wilton Manors, FL
James Montgomery Flagg (1877-1960) Portrait of F. Scott Fitzgerald, ca. 1925. Ink and pencil on illustration board, image measures 9 x 15 inches; 17 x 21 inches framed. Signed lower right. Annotated with name of subject on verso in pencil by the artist. Very good condition with no damage or conservation. Original glue residue in margins. An outstanding a rare example of Flagg's sketch portraiture. While the artist is most famous for illustration work, Flagg loved to make quick sketches of famous society friends and patrons. The piece clearly belongs to the latter category with looser brushwork suggesting famous contemporary American portrait painters that he admired. The image documents a quiet, intimate moment in the lives of both artist and subject. Provenance: John Francis Lee, former president of Stoney Brook College, Long Island, (1918-1999). Annotated on verso in blue ink. James Montgomery Flagg (1877-1960) During a long and fruitful career, James Montgomery Flagg produced an immense and varied amount of artwork. A popular social gadabout and the life of a party, Flagg was constantly sketching friends, celebrities and politicians and always surrounded by beautiful models and sycophants. He clearly enjoyed his own ability at humor and satire as well as his fame as an illustrator. By the age of twelve he was selling his drawings and cartoons to St. Nicholas magazine. At the age of fifteen, he was a staff artist for both Judge and Life magazines, two of the nation¹s most successful periodicals. Flagg grew up in the period when pen and ink ruled and printing technology was limited. When halftone printing was accepted as a reproduction process, Flagg created images of beautiful women, which supplanted the portrait artists of previous decades. It is true that Gibson had created a sensation with his early notion of a beautiful American girl, but Christy, Fisher and Flagg did likewise, with each of them producing early versions of coffee table books and magazine illustrations heralding a new world of fashion, styles, and beauty. The society portraits created by John Singer Sargent were thusly thrown asunder and whole new prototypes of American beauty were created-bustles and chastity were disappearing and the illustrators ushered in a new era. Flagg studied at the Art Students League in New York City (1894-1898), and then in London and Paris (1898-1900). He was an active member of the Society of Illustrators, The Players Club, The Dutch Treat Club, and the Lotos Club-where he personally hung his poignant editorial cartoons in the grille room. In 1898, he went to England to further his art studies and enrolled at the Herkomer School in Bushey, Hertfordshire an art school founded by Professor Hubert von Herkomer, the art critic who heralded Maxfield Parrish¹s work in critical reviews. Upon his return from Europe, he created a comic strip 'Nervy Nat,' which gained immediate popularity winning him the commission for P.G. Wodehouse's stories where he created the visual characterization for the character 'Jeeves'. The first book he illustrated was Yankee Girls Abroad (1900), with pretty gals abounding who were superficially similar to The Christy Girl and Fisher's American Girl. Flagg's notion was yet another example of what American's thought our women should look like. His commissions ranged from cartoons, posters, magazine covers and inside illustrations, and advertisements to serious portraits, which were exhibited in the Paris Salon of 1900 alongside the academic painters from the Academie Julian. Books illustrated include An Orchard Princess, Simon the Jester, City People, Brinkley Manor, The Adventures of Kitty Cobb and in 1932 the seminal pin-up work, Virgins in Cellophane. In 1946, his published his autobiography, Roses and Buckshot. The magazines with his works included Colliers, Cosmopolitan, Hearst's International, Judge Magazine, Liberty, Life, McClures Magazine, Photoplay, Redbook, Saturday Evening Post, The American Weekly, Women¹s Home Companion, and many others. Flagg was a favorite illustrator of publishing tycoon William Randolph Hearst and due to their relationship he gained numerous other commissions including humorous short story illustrations (which he enjoyed doing most), and rapid portrait studies of Hearst's friends. Most of his sitters were generally upper-class society scions and celebrities including: actor John Barrymore and his sister Ethel, cartoonist Ham Fisher, unique humorist Rube Goldberg, and illustrator Charles Dana Gibson. However, James Montgomery Flagg remains best known for a single painting, his iconic illustration of Uncle Sam proclaiming, 'I Want You' for a US Army Recruiting...
Category

1920s American Impressionist James Montgomery Flagg Paintings

Materials

Ink, Illustration Board, Pencil

James Montgomery Flagg paintings for sale on 1stDibs.

Find a wide variety of authentic James Montgomery Flagg paintings available for sale on 1stDibs. You can also browse by medium to find art by James Montgomery Flagg in ink, board, paper and more. Not every interior allows for large James Montgomery Flagg paintings, so small editions measuring 15 inches across are available. Customers who are interested in this artist might also find the work of Alex Ross, Alfred Munnings, and Henry Soulen. James Montgomery Flagg paintings prices can differ depending upon medium, time period and other attributes. On 1stDibs, the price for these items starts at $3,900 and tops out at $7,500, while the average work can sell for $5,500.