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
781
716
711
693
2
1
3
Artist: James Montgomery Flagg
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

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

“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

Ink, Board, Paper, Pencil

Related Items
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

Georgian Contemporary Art by Keta Jikia - Untitled 10
Located in Paris, IDF
Oil, charcoal & ink on cardboard Keta Jikia is a Georgian artist born in 2002 who lives and works in Tbilisi, Georgia. She is graduated in 2025 with a degree in International Relati...
Category

2010s Contemporary James Montgomery Flagg Paintings

Materials

Oil, Ink, Cardboard

Allegory of Love, Cupid With Beauty in Fine Dress Carrying a Basket of Flowers
Located in Cotignac, FR
A late 18th Century oil on canvas laid on board of a young beauty in period costume carrying a basket of flowers on her head. Presented in a very fine gilt, period 'Directoire' frame...
Category

Late 18th Century Romantic James Montgomery Flagg Paintings

Materials

Canvas, 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

Maritime Scene with Sailboats
Located in Stockholm, SE
This captivating maritime painting, likely the work of an English artist, dates to the late 19th century and showcases a masterful command of light and texture. The composition featu...
Category

Late 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

Early 19th Century English watercolour of woodland near Croxdale Hall
Located in Harkstead, GB
A very attractive and meticulously executed view of a rocky landscape within the woods dating to 1823. This would suit a library or study with its muted tones and skifull draughtsmanship. William Nicholson (1781-1844) Near Croxdale Hall Signed with initials and inscribed with title and date 1823 Pen, ink and grey wash 11 x 8 inches, image only 17 x 13 inches without frame The portrait-painter and etcher William Nicholson was born in Ovingham-on-Tyne, Northumberland, on Christmas Day 1781. His family transferred to Newcastle when his father was appointed Headmaster of the city's Grammar School. At an early age, though, Nicholson appears to have moved to Hull where he made his artistic debut, painting miniatures of officers garrisoned there. He was almost entirely self-taught, learning his craft through the close study of artworks in private and public galleries. He subsequently returned to Newcastle where he received many commissions to paint portraits of the old families of Northumberland. In 1808, he began to exhibit at the Royal Academy, continuing to do so until 1822. By 1814, Nicholson, whose mother was a Scot, had moved to Edinburgh where he set up as a miniaturist and painter in oils. Soon, however, he began to specialize in watercolour portraits. Early subjects included the actor Daniel Terry and the poet and novelist James Hogg. In 1818 he began to publish a series of Portraits of Eminent Scotsmen, etched from his own portraits and those of other painters. Besides Scott and Hogg, the subjects included the writers Robert Burns, John Wilson ('Christopher North'), and Lord Jeffrey, the painters Sir Henry Raeburn, the divines Alexander Carlyle and Alexander Cameron, the engineer James Watt, the architect John Playfair, and the song-collector and composer George Thomson...
Category

Early 19th Century Academic James Montgomery Flagg Paintings

Materials

Paper, Watercolor, Ink, Pen

View of a Mansion in the South of France, a drawing by Claude-Joseph Vernet
By Claude-Joseph Vernet
Located in PARIS, FR
We would like to thank Madame Beck-Saiello for confirming the autograph nature of this drawing after an in-person examination. It was probably during an excursion in the countryside near Avignon that Claude-Joseph Vernet executed this drawing, enhanced with pen and brown ink, depicting a mansion on a hilltop overlooking a small village with geometric shapes. 1. Joseph Vernet, a painter influenced by Italy Claude-Joseph Vernet was born in Avignon in 1714, the son of Antoine Vernet (1689-1753), an artisan painter of architectural decorations, coach panels, and the like. He moved to the studio of Philippe Sauvan (1697-1792), a leading history painter in Avignon, and then worked with Jacques Viali (active 1681-1745), a decorative, landscape, and marine painter in Aix-en-Provence. Vernet's first recorded paintings were decorative overdoors executed in 1731 in the Aix townhouse of the marquise de Simiane. In 1734, Joseph de Seytres, marquis de Caumont, a leading amateur in Avignon, sponsored Vernet to make a study trip to Italy to complete his artistic education and to draw antiquities for his patron. As Avignon was a papal territory in Vernet's day, he also had a number of useful introductions among influential churchmen when he arrived in Rome. Vernet was soon at home in the French community there, and he was encouraged by Nicolas Vleughels (1668-1737), director of the Académie de France in Rome, even though the young painter had no official affiliation with the royal institution. He likely entered the studio of the French marine painter Adrien Manglard...
Category

1730s Old Masters James Montgomery Flagg Paintings

Materials

Ink, Laid Paper, Pen, Carbon Pencil

Cottages in Upper Slaughter, Original painting, cotswolds, Landscape
By Elizabeth Chapman
Located in Deddington, GB
Pen & Ink Drawing with Watercolour on Watercolour Paper. Drawn on a winters day in Upper Slaughter. The artist lives in the Cotswolds close to Upper Slaughter. ADDITIONAL INFORMATIO...
Category

2010s Contemporary James Montgomery Flagg Paintings

Materials

Paper, Ink, Pen

Mona Lisa Mickey Mouse Manga Cartoon Pop Art by British Urban Graffiti Artist
By Chris Pegg
Located in Preston, GB
Mona Lisa Mickey Mouse Manga Cartoon Pop Art by British Urban Graffiti Artist, Chris Pegg. This striking mixed media artwork by Chris Pegg exemplifies his vibrant, satirical style t...
Category

2010s Pop Art James Montgomery Flagg Paintings

Materials

Metal

'A winter landscape with an ox-cart' by Willem De Klerk (1800 – 1876)
Located in Knokke, BE
Willem De Klerk 1800 – Dordrecht – 1876 Dutch Painter 'A winter landscape with an ox-cart on a wooded road near a village' Signature: signed lower left ‘W. de Klerk f’ Medium: oi...
Category

Early 19th Century Romantic James Montgomery Flagg Paintings

Materials

Ink, Watercolor, Pencil

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

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.

Recently Viewed

View All