A Picture Is Worth...
When it comes to the photographs on this list—they are worth way more than a thousand words or even a thousand dollars, or a hundred thousand dollars. We're talking millions here. But how many millions? Take a guess... Now see if you're right.
Pantheon, Rome (1990-1992)
Tourist photographs aren't generally worth much to anyone but the tourists who took them—but Thomas Struth's series of "Museum Photographs" (mostly taken at the Pantheon) are worth a fortune. One in the series, showing tourists in the Pantheon, sold for $1,810,000 in 2016.
Portrait Of A Tearful Woman (1936)
Portrait of a Tearful Woman is a hand painted photograph by famed artist Man Ray (born Emmanuel Radnitzky). Meaning, it began as a black and white photo that Ray then turned into a color image painting it by hand.
In 2017, a print of this photograph was auctioned off at Christie's, New York. It was predicted to sell for somewhere between $400,000-$600,000. The final bid was $2,167,500.
Carl Van Vechten, Wikimedia Commons
Untitled Film Still #48 (1979)
Also known as The Hitchhiker, this black and white photograph of a woman standing on the side of the road is one photograph from artist Cindy Sherman's Untitled Film Stills photographic series.
Three prints of this image have sold for millions of dollars. One sold in 2008 for $1,565,000. A second sold in 2014 for $2,225,000. And a third...we'll get to that one a little later on.
99 Cent II Diptychon (2001)
While everything in a 99 cent store costs 99 cents (or at least it used to), this diptych photograph of the inside of a Los Angeles 99 cent store sold at auction for a whole lot more than 99 cents. German photographer Andreas Gursky's colorful critique of consumer society sold at auction in May of 2006 for $2,250,000.
Hpschaefer, CC BY-SA 3.0, Wikimedia Commons
99 Cent (1999)
Andreas Gursky's aforementioned diptych was actually based on a photograph he took two years prior, titled 99 Cent. That image—called one of the 100 most important photographs ever taken by Time magazine—also sold at a May 2006 auction. It went for $2,256,000.
Billy The Kid Tintype Portrait (1879–80)
No one knows who took it, or when exactly it was taken—but that doesn't make this tintype photograph portrait of Billy the Kid any less amazing. So much so that at Brian Lebel's Old West Show & Auction in 2011, it sold for $2,300,000.
Ben Wittick, Wikimedia Commons
Paris, Montparnasse (1993)
No artist appears on this list more often than Andreas Gursky. For his 1993 work, Paris, Montparnasse, Gursky used digital manipulation to create this amazing 210 by 395 cm image of the Immeuble d’habitation Maine-Montparnasse II, in the Rue Commandant-Mouchotte of Paris. There were five copies of this photograph produced—and in 2013, one of them sold for $2,416,475.
99 Cent II Diptychon (2001)
In November of 2006—six months after the other 99 Cent II Diptychon had sold for $2,250,000—another copy of the image went for $2,480,000 at Phillips de Pury & Co New York.
Hpschaefer, CC BY-SA 3.0, Wikimedia Commons
Chicago Board Of Trade (1997)
Stockbrokers fill "the pit" on the floor of the Chicago Board of Trade in the bustling, capitalist environment of this Andreas Gursky photograph. Gursky made six editions of this photo, but the one in question is the original and often referred to as Chicago Board of Trade I.
Sotheby's London auctioned a print of this photograph off in 2013 for $2,507,755.
Untitled #153 (1985)
Vanity Fair asked Cindy Sherman to create a series of photographs inspired by fairy tales. The magazine didn't end up using any of them, but their value sure didn't suffer because of it. Untitled #153 looks like a crime scene photo (not sure what fairytale it represents) and there are prints of it at museums all over the world, including: The Museum of Modern Art, New York, the Museum of Contemporary Art, Chicago, the Musée d'art contemporain de Montréal, The Israel Museum, Jerusalem, and the Museo Rufino Tamayo, Mexico City.
There is also a print in some collector's house. A collector who paid $2,770,500 for it at a 2010 auction.
New Zealand Government, CC BY 4.0, Wikimedia Commons
Untitled (Cowboy) (2000)
Untitled (Cowboy) is a photographic reproduction of a photograph by Sam Abell created by American painter and photographer Richard Prince. In 2007, Christie's New York auctioned off a print for $2,840,000.
Wiktor Szymanowicz, Getty Images
Untitled #96 (1981)
We're starting to get the feeling that Cindy Sherman doesn't like to title her pieces. Untitled #96 is part of her 12-photograph Centerfolds series—and in this photo, Sherman is dressed up as a teen girl lying down on a very 60s-inspired linoleum floor. The 1981 photograph sold in 2012 for $2,882,500.
Los Angeles (1998)
Say hello to Gursky again. This time with a photograph titled Los Angeles—a nighttime photo taken from the Griffith Observatory looking out across LA, lit up by city lights, with a pitch black sky above. At about eight feet wide, it is a huge print—and it fetched a huge price at a 2008 Sotheby's London auction: $2,900,000.
picture alliance, Getty Images
The Pond—Moonlight (1904)
With the application of light-sensitive gums, Edward Steichen was able to get more colors out of his 1904 photograph. It also meant that each version of the image is unique. There are only three still in existence and in 2006, one of those three was bought at auction for $2,928,000.
Edward Steichen, Wikimedia Commons
Untitled Film Still #48 (1979)
The third print of this Cindy Sherman photograph series (remember The Hitchhiker one?) went for $2,965,000 at a 2015 auction at Christie's New York.
Untitled (Cowboy) (1997)
Richard Prince made a number of these Untitled (Cowboy) pieces. This one, from 1997, sold in 2021 for $3,030,000.
Drpaluga, CC BY-SA 3.0, Wikimedia Commons
Untitled (Cowboy) (2000)
Back to the 2000 Untitled (Cowboy)—This one saw the gavel come down at $3,077,000 at a 2014 auction at Sotheby's New York.
Noire Et Blanche (1926)
For those who don't speak French, “Noire et Blanche" translates to "black and white" and has a double meaning representing both the black and white photography and the contrasting image of the Caucasian woman and the African mask in the photo. This Man Ray work sold for $3,131,533 in 2017.
Tim Evanson, CC BY-SA 2.0, Wikimedia Commons
Chicago Board Of Trade III (1999-2009)
The third version of the original Chicago Board of Trade photograph we talked about earlier. Chicago Board of Trade III had an estimated price of $1,200,000—but sold at a 2013 auction for $3,298,755 (that's a 169% increase).
The Perception Machine: David England on Andreas Gursky, Liverpool John Moores University
99 Cent II Diptychon (2001)
People love this one—as you can tell from it already having shown up twice on our list. But while the other two sales had seen the final price in the $2 million range, in 2007, it sold at auction for $3,346,456. That made it the first photograph to sell at auction for more than $3 million and the most expensive photograph in the world (at the time).
Andreas Gursky at the Hayward Gallery, The Art Channel
Untitled (Cowboy) (2001-2002)
And yet more Untitled (Cowboy) fun—this one fetched $3,401,000 at a 2007 auction. Taking place nine months after the Gursky photograph topped $3 million, Prince's "cowboy" took over the top spot.
Untitled (Cowboy): Behind Richard Prince's Photographs & Appropriation, TIME
Untitled (Cowboy) (2000)
A 2016 auction at Christie's New York saw this Untitled (Cowboy) sell for $3,525,000.
Untitled (Cowboy): Behind Richard Prince's Photographs & Appropriation, TIME
Dead Troops Talk (1992)
The full title of this photograph is: Dead Troops Talk (A vision after an ambush of a Red Army patrol, near Moqor, Afghanistan, winter 1986). Rather than an actual photograph taken during a war, Jeff Wall created a staged post-attack visual with soldiers rising from the dead. The image went for $3,666,500 at an auction in 2012.
Pmussler, CC BY-SA 3.0, Wikimedia Commons
Untitled (Cowboy) (1998)
2014 saw the highest price paid for one of Richard Prince's Untitled (Cowboy) pieces. This one closed at $3,749,000.
To Her Majesty (1973)
Gilbert Proesch and George Passmore, better known as the collaborative art duo Gilbert & George, created the To Her Majesty piece in 1973. In 2008, it sold for $3,765,276.
Edwardx, CC BY-SA 4.0, Wikimedia Commons
Untitled #93 (1981)
Another image from her Centerfolds series, this one finds Sherman in bed looking like "somebody who'd been up all night drinking and partying and had just gone to sleep five minutes before the sun rose and woke her up". Sotheby's New York auctioned this print off for $3,861,000 in 2014.
Cindy Sherman in "Transformation" - Season 5 - "Art in the Twenty-First Century", Art21
Untitled #96 (1981)
In 2011, Untitled #96 became the most expensive photograph ever, when it sold for $3,890,500.
Cindy Sherman in "Transformation" - Season 5 - "Art in the Twenty-First Century", Art21
Spiritual America (1981)
This very controversial piece by Richard Prince forgoes the cowboys and instead uses a photograph of a 1975 photograph of a 10-year-old Brooke Shields. Let's just say that it isn't hard to see why it was so controversial. But it also sold in 2014 for $3,973,000.
Patrick McMullan, Getty Images
Rhein II (1999)
With a sale price of $4,338,500, in November of 2011, Andreas Gursky's photograph of the Lower Rhine river became the most expensive photograph of all time. And it held onto that record until 2022.
picture alliance, Getty Images
Phantom (?)
In 2014, Aussie photographer Peter Lik claimed to have sold a photograph titled Phantom to an anonymous bidder for $6.5 million. However, the sale has never been proven and the buyer has not come forward. Although a lawyer claiming to represent the buyer does say that it is true.
Bagima, CC BY-SA 3.0, Wikimedia Commons
The Flatiron (1904)
The Flatiron is a truly beautiful photograph by Edward Steichen, of the Flatiron building in New York City (it had just recently been built when the photo was taken). In November 2022, a print sold for $11,800,000 (way above the $2,000,000–3,000,000 estimate).
But that huge price didn't make it the most expensive photograph ever—because of what had happened just six months earlier...
Edward Steichen, Wikimedia Commons
Le Violon d'Ingres (1924)
Le Violon d'Ingres is Man Ray's iconic photograph of the surrealist movement, and features model Kiki de Montparnasse sitting nude with her back to the camera—with two f-holes painted on the image to make her body look like a violin. It became the most expensive photograph the world has ever known, when it sold for $12,400,000 on May 14, 2022.
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Carl Van Vechten, Wikimedia Commons
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