10 Artist Portraits to Collect at Auction

Photographers often take portraits of fellow artists, providing glimpses into their personal relationships and everyday lives. From Georgia O’Keeffe to Pablo Picasso, discover 10 photographs of art history’s greatest icons, as well as the stories behind these lasting snapshots.

These photographs are all available at auction this week—and you can bid on your favorites by clicking on the images below.


Georgia O’Keeffe by Alfred Stieglitz

From 1917 to 1937, Alfred Stieglitz photographed over 300 portraits of the painter Georgia O’Keeffe, tracking their relationship from friends to lovers to husband and wife.

Estimated value: $10,000–15,000


John Lennon and Yoko Ono by Annie Leibovitz

This famous photograph captures John Lennon, embracing his partner and Fluxus artist Yoko Ono, just hours before his untimely death.

Estimated value: $20,000–30,000


Andy Warhol by Allen Tannenbaum

“At the Mudd Club mistakes could pass as exper­i­ments,” Andy Warhol once said about the Tribeca club, pictured here, that served as the second home to many icons of the1970s art scene.

Estimated value: $2,200


Francis Bacon and Lucian Freud by Harry Diamond

Taken in 1974, this photograph captures Francis Bacon and Lucian Freud at a pivotal point in their relationship, as their friendship transitioned towards rivalry.

Estimated value: $2,000–3,000

Gerhard Richter by Thomas Struth

In 1993, Thomas Struth photographed his former professor, the painter Gerhard Richter, who decades earlier had encouraged Struth to leave painting to study photography with the legendary duo Bernd and Hilla Becher.

Estimated value: $50,000–70,000


Barnett Newman by Irving Penn

Irving Penn is known for his austere portraits, and this close-up of the monocle-wearing Abstract Expressionist painter is no exception.

Estimated value: $15,000–25,000


Lee Miller by Man Ray

Lee Miller was Man Ray’s beloved muse, studio assistant, lover, and friend—but she was also an artist in her own right and hid her own photographs in the attic of her farmhouse, which were discovered and published after her death.

Estimated value: $80,000–120,000


Pablo Picasso by Arnold Newman

Arnold Newman is known for his revealing portraits of 20th-century icons, such as Pablo Picasso, Marilyn Monroe, and Edward Hopper, in their homes and studios.

Estimated value: $9,000


Cy Twombly by Robert Rauschenberg

In 1952, Cy Twombly and Robert Rauschenberg journeyed to Europe together and photographed their travels—coincidentally, they visited Rome at the same time Roman Holiday was being filmed there.

Estimated value: $10,000–15,000


Henri Matisse by Henri Cartier-Bresson

Henri Cartier-Bresson provides an inside look into Henri Matisse’s practice, documenting the artist holding a dove in one hand and sketching with the other.

Estimated value: $6,000–8,000

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