A stern, spectacled Rough Rider stares out from a pale ground, his features reduced to cool blocks of tone. It is one of the most recognizable presidential images in Pop Art, and it is often called Andy Warhol's Teddy Roosevelt painting. The real story involves a print, a portfolio, and a myth about the American West that Warhol held up for inspection.
TL;DR: The Warhol Teddy Roosevelt most people mean is a 1986 screenprint, catalogued as F&S II.386, from the ten-print portfolio Cowboys and Indians, one of the last series Warhol completed before his death in February 1987. It is based on an 1898 photograph of Roosevelt in his Rough Rider uniform, measures about 36 x 36 inches on Lenox Museum Board, and was published in a standard edition of 250. A signed impression sold for $88,900 at Rago in October 2025.
Table of Content
- The Image Everyone Calls a Painting
- Inside the Cowboys and Indians Portfolio
- From Rough Rider Photo to Pop Icon
- What Warhol's Roosevelt Says
- Collecting Warhol's Teddy Roosevelt Today
- Warhol's Teddy Roosevelt: Collector Questions Answered
The Image Everyone Calls a Painting
Search for the famous Warhol painting of Teddy Roosevelt and you will land on a screenprint. The Roosevelt image that hangs in collections and fills auction catalogs is a color screenprint from 1986, produced in an edition rather than as a single canvas.
That choice fits Warhol's training. He earned his degree in 1949 from the Carnegie Institute of Technology, now Carnegie Mellon University, where he studied pictorial design, then moved to New York and worked as a commercial illustrator before turning mass-produced images into fine art. How he did that, compared with his great Pop rival, is the subject of Roy Lichtenstein vs. Andy Warhol.
Teddy Roosevelt at a Glance
| Detail | Information |
|---|---|
| Title | Teddy Roosevelt, from Cowboys and Indians |
| Date | 1986 |
| Catalogue number | Feldman & Schellmann II.386 |
| Medium | Color screenprint on Lenox Museum Board |
| Size | About 36 x 36 in. (91.4 x 91.4 cm) |
| Edition | 250, plus proofs |
| Printer | Rupert Jasen Smith, New York |
| Publisher | Gaultney-Klineman Art Inc., New York |
Inside the Cowboys and Indians Portfolio
Cowboys and Indians gathers ten portraits and objects from the story of the American West: John Wayne, Annie Oakley, General Custer, Geronimo, Teddy Roosevelt, Mother and Child, Indian Head Nickel, Kachina Dolls, Northwest Coast Mask, and Plains Indian Shield. The 36 trial proof sets add four more images: War Bonnet Indian, Buffalo Nickel, Action Picture, and Sitting Bull.
For the Native objects, Warhol photographed a Plains Indian shield, a Northwest Coast mask, and kachina dolls at New York's Museum of the American Indian. That collection later became the foundation of a Smithsonian museum, the National Museum of the American Indian.
Museums keep returning to the series. Wichita State University's Ulrich Museum of Art featured the portfolio in its 2022 exhibition Myths of the West, and the traveling show Warhol and the West visited the Booth Western Art Museum, the National Cowboy & Western Heritage Museum, and the Tacoma Art Museum in 2019 and 2020. The Ulrich's short video offers a closer look:
From Rough Rider Photo to Pop Icon
The source is an 1898 photograph of Lieutenant Colonel Theodore Roosevelt in his Rough Rider uniform. Gallery documentation credits the image to the Theodore Roosevelt Collection at Harvard's Houghton Library, which holds Roosevelt's diaries, correspondence, photographs, cartoons, and ephemera.
The moment matters. Roosevelt resigned as assistant secretary of the Navy when war with Spain broke out, organized the volunteer cavalry known as the Rough Riders, and became a national figure after the charge up Kettle Hill, as the National Portrait Gallery recounts. Within weeks of the regiment disbanding he was running for governor of New York, and by 1901 he was the 26th president. Warhol chose the uniform over the White House, the frontier hero over the statesman.
Turning history into legend is an old American habit. Grant Wood, the Iowa painter, played with the same kind of national myth in Parson Weems' Fable (1939), his take on George Washington and the cherry tree.
From Rough Rider to Pop Icon
Sources: Revolver Gallery, Teddy Roosevelt 386B; Rago Auctions, Lot 100; Guy Hepner, Teddy Roosevelt F.S. II.386
What Warhol's Roosevelt Says
Two readings sit side by side. One sees a celebration: Roosevelt as rancher, soldier, conservationist, and president, rendered as confidently as a movie poster. The other, favored by many critics and dealers, sees a pointed juxtaposition. Placed beside Geronimo and Mother and Child, the cool, stony treatment of Roosevelt can read as a comment on his record toward Native Americans and on the romantic story of the frontier.
Warhol removed his subjects from any landscape and set them against plain grounds, echoing the way film and television flattened the West into costumes and props. The result asks viewers which parts of the national story are history and which are branding. For the bigger picture of how artists have handled that question, see the history of Americana art and what Americana means to American culture.
The print also makes an instructive contrast with Edward Hopper, the American realist, whose quiet scenes of ordinary life sit at the opposite end of the Americana spectrum from Warhol's loud, celebrity-driven icons.
Collecting Warhol's Teddy Roosevelt Today
Edition details matter. Beyond the standard edition of 250, the print exists in 50 artist's proofs, 15 printer's proofs, 15 hors commerce impressions, 10 impressions numbered in Roman numerals, and 36 trial proofs, each trial proof a unique color variation.
Rago Auction Result, October 2025
Source: Rago Auctions, Andy Warhol, Teddy Roosevelt (Lot 100)
At that sale, impression 239/250, signed and numbered in pencil with the printer's blindstamp, sold for $88,900 against an estimate of $30,000 to $50,000. Before buying, confirm the F&S II.386 reference, the pencil signature and numbering, and the blindstamp; inspect the Lenox Museum Board for fading, corner wear, and staining; and ask for a clear provenance trail. Unsigned impressions and later reproductions circulate too, and they are valued very differently.
Not every Americana collector needs a blue-chip Warhol. If you love bold portraits of American icons with painterly energy, original canvases from Steve Penley Art offer a hand-painted take on the same national heroes.
Warhol's Teddy Roosevelt: Collector Questions Answered
Is Warhol's Teddy Roosevelt a painting or a print?
The widely known version is a 1986 color screenprint on Lenox Museum Board, catalogued as F&S II.386, even though it is often called a painting.
When did Warhol make Teddy Roosevelt?
In 1986, as part of Cowboys and Indians, one of the last portfolios he completed before his death in February 1987.
How many Teddy Roosevelt prints exist?
The standard edition is 250, supplemented by artist's proofs, printer's proofs, hors commerce impressions, Roman numeral impressions, and 36 unique trial proofs.
What photograph is it based on?
An 1898 photograph of Lieutenant Colonel Roosevelt in his Rough Rider uniform, credited to the Theodore Roosevelt Collection at Harvard's Houghton Library.
How much is Warhol's Teddy Roosevelt worth?
Prices vary with condition, edition type, and market timing. A signed standard impression sold for $88,900 at Rago in October 2025, well above its $30,000 to $50,000 estimate, so consult a print specialist for a current valuation.
Keep reading: meet more famous Pop Art artists, or browse the Penley Americana collection.