March 3, 2025 | Jesse Singer

The Most Expensive Photographs Ever Sold At Auction


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.

Thomas Struth Pantheon, Rome Photography at The Museum of Modern ArtAndrew Milligan, Flickr

Advertisement

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.

Grayscale Portrait Photo of American visual artist Man RayCarl 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.

Cindy Sherman attends the Time 100 Gala at Frederick P. Rose HallDebby Wong, Shutterstock

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.

German photographer Andreas Gursky at museum K21, DüsseldorfHpschaefer, CC BY-SA 3.0, Wikimedia Commons

Advertisement

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.

A woman stands in front of the image entitled '99 Cent' by Andreas GurskyTF-Images, Getty Images

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.

Billy The Kid tintype at Fort Sumner, New Mexico, circa 1879-80Ben 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.

A gallery assistant poses in front of a work by German photographer Andreas Gursky entitled 'Paris, MontparnasseDANIEL LEAL, Getty Images

Advertisement

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.

German photographer Andreas Gursky at museum K21, DüsseldorfHpschaefer, 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.

Newly Refurbished Hayward Gallery Opens With Andreas Gursky RetrospectiveLeon Neal, Getty Images

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.

Artist Cindy Sherman, at a lunch in her honour at Government HouseNew Zealand Government, CC BY 4.0, Wikimedia Commons

Advertisement

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.

Art handlers look at a print by Richard Prince 'Untiled (Cowboy)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.

A woman takes a photograph of STAN HONDA, Getty Images

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.

Andreas Gursky at Presentation of the Sparkasse Culture Prizepicture alliance, Getty Images

Advertisement

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.

The Pond—Moonlight is a pictorialist photograph by Edward SteichenEdward 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.

Cindy Sherman attends New Museum's 2024 Spring GalaDominik Bindl, Getty Images

Untitled (Cowboy) (1997)

Richard Prince made a number of these Untitled (Cowboy) pieces. This one, from 1997, sold in 2021 for $3,030,000.

Portrait Photo of American painter and photographer Richard PrinceDrpaluga, CC BY-SA 3.0, Wikimedia Commons

Advertisement

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.

Richard Prince, with a piece from his solo show Regan ProjectsRick Loomis, Getty Images

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.

The photograph 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).

David England on Andreas Gursky at The Perception MachineThe Perception Machine: David England on Andreas Gursky, Liverpool John Moores University

Advertisement

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 ChannelAndreas 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.

Behind Richard Prince's Photographs & AppropriationUntitled (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.

Behind Richard Prince's Photographs & AppropriationUntitled (Cowboy): Behind Richard Prince's Photographs & Appropriation, TIME

Advertisement

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.

Jeff Wall at the 2014 Paris Photo fair in Los Angeles.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.

Richard Prince during Richard Prince Check Paintings at Gagosian GalleryJeff Kravitz, Getty Images

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.

Gilbert & George, Hatchards, London, 29 November 2023Edwardx, CC BY-SA 4.0, Wikimedia Commons

Advertisement

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, from the 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, from the 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.

Richard Prince attends Damien Hirst: Superstition Gallery OpeningPatrick McMullan, Getty Images

Advertisement

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.

View of the work 'Rhein II, 1999/2015' during a preview at Kunstsammlung Nordrhein-Westfalen in Duesseldorfpicture 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.

 Grayscale Portrait Photo of Australian photographer Peter LikBagima, 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...

The Flatiron is a colored photograph made by Edward SteichenEdward Steichen, Wikimedia Commons

Advertisement

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.

You might also like:

How The World's Youngest Billionaires Acquired Their Monumental Fortunes

Surprising Things Americans Spend Their Money On

Best-Selling Products From The Decade You Were Born

Grayscale Portrait Photo of American visual artist Man Ray 1934Carl Van Vechten, Wikimedia Commons

Sources: 1


READ MORE

Retirement Planning Internal3

10 Brilliant And Fun Ways To Beef Up Your Retirement Bankroll

Discover ten fun and easy strategies to boost your retirement income. Transform your golden years into an exciting new phase of life with these practical financial tips. Dive into dividend-paying stocks, explore peer-to-peer lending, consider annuities, and more. Add a twist to your retirement planning and make your relaxation years even more rewarding.
September 15, 2023 Allison Robertson

The Most Dangerous Jobs in the World

Discover the 15 most dangerous jobs in the world, and how much they pay. Learn about danger pay, PPE, and the risks associated with each job.
December 12, 2023 Allison Robertson
Cheap Hobbies Internal

Beat the Cold Without Burning Cash: Unique Indoor Hobbies on a Budget

Discover 15 unique and budget-friendly indoor hobbies perfect for the cold winter months. From DIY crafting to culinary experiments, this guide offers creative ways to stay entertained without straining your wallet. Dive into these cost-effective pastimes and make the most of your indoor time.
September 15, 2023 Allison Robertson

The True Cost of Cheap: Why Opting for Lower Prices Now Might Cost You Later

Explore the unforeseen pitfalls and hidden costs of opting for cheaper products. This in-depth article unravels the financial, ethical, and personal impacts of choosing lower-priced items and provides alternatives to help you make savvy, sustainable spending decisions, ensuring your choices are economical and ethical in the long run.
October 15, 2023 Miles Brucker

The Least Desirable Jobs

Discover 10 jobs that pay well that nobody wants to do. From working with lifeless bodies to crab fishing, find out why these jobs are not desirable and how much they pay.
January 11, 2024 Allison Robertson

Top 10 Careers of 2023: Where Opportunity Meets Demand

Discover the top 10 best jobs of 2023, encompassing sectors like technology, healthcare, renewable energy, and digital marketing. Learn about the roles, salaries, and reasons why these jobs stand out in today's evolving job market, offering exciting opportunities for professionals across various industries.
November 20, 2023 Allison Robertson



Dear reader,


It’s true what they say: money makes the world go round. In order to succeed in this life, you need to have a good grasp of key financial concepts. That’s where Moneymade comes in. Our mission is to provide you with the best financial advice and information to help you navigate this ever-changing world. Sometimes, generating wealth just requires common sense. Don’t max out your credit card if you can’t afford the interest payments. Don’t overspend on Christmas shopping. When ordering gifts on Amazon, make sure you factor in taxes and shipping costs. If you need a new car, consider a model that’s easy to repair instead of an expensive BMW or Mercedes. Sometimes you dream vacation to Hawaii or the Bahamas just isn’t in the budget, but there may be more affordable all-inclusive hotels if you know where to look.


Looking for a new home? Make sure you get a mortgage rate that works for you. That means understanding the difference between fixed and variable interest rates. Whether you’re looking to learn how to make money, save money, or invest your money, our well-researched and insightful content will set you on the path to financial success. Passionate about mortgage rates, real estate, investing, saving, or anything money-related? Looking to learn how to generate wealth? Improve your life today with Moneymade. If you have any feedback for the MoneyMade team, please reach out to [email protected]. Thanks for your help!


Warmest regards,

The Moneymade team