The past twelve years has seen a new photograph enter the top 50 most expensive photographs ever sold at auction, every single year. In the past decade, there have been ten new entrants into the top 20. The following is The Top 20 Most Expensive Photographs Sold At Auction, updated to November 2022. For more entries, view the Photography At Auction Digest.

20

Man Ray Portrait of a tearful woman. Sold at Christie’s New York in May 2017. $2,167,500

19

Cindy Sherman Untitled Film Still 48. Sold at Sotheby’s New York in November 2014. $2,225,000

18

Unknown Artist Billy The Kid. Sold at Brian Lebel’s Old West Show & Auction in June 2011. $2,300,000

17

Andreas Gursky Chicago Board of Trade I. Sold at Sotheby’s London in June 2013. $2,353,905

16

Andreas Gursky Paris, Montparnasse. Sold at Sotheby’s London in October 2013. $2,386,825

15

Cindy Sherman Untitled 153. Sold at Phillips New York in November 2010. $2,770,500

14

Cindy Sherman Untitled 96. Sold at Christie’s New York in March 2012. $2,882,500

13

Edward Steichen The Pond – Moonlight. Sold at Sotheby’s New York in February 2006. $2,928,000

12

Andreas Gursky Los Angeles. Sold at Sotheby’s London in February 2008. $2,938,235

11

Cindy Sherman Untitled Film Still 48. Sold at Christie’s New York in May 2015. $2,965,000

10

Richard Prince Untitled (cowboy). Sold at Sotheby’s New York in May 2014. $3,077,000

9

Man Ray Noire et Blanche. Sold at Christie’s Paris in November 2017. $3,118,950

8

Andreas Gursky Chicago Board of Trade III. Sold at Sotheby’s London in June 2013. $3,296,385

7

Andreas Gursky 99 Cent II Diptychon. Sold at Sotheby’s London in February 2007. $3,332,000

6

Jeff Wall Dead Troops Talk. Sold at Christie’s New York in May 2012. $3,666,500

5

Gilbert & George To Her Majesty. Sold at Christie’s London in June 2008. $3,759,607

4

Cindy Sherman Untitled 96. Sold at Christie’s New York in May 2011. $3,890,500

3

*Richard Prince Spiritual America. Sold at Christie’s New York in May 2014. $3,973,000

2

Andreas Gursky Rhein II. Sold at Christie’s New York in November 2011. $4,338,500

1

Edward Steichen The Flatiron. Sold at Christie’s New York in November 2022. $11,840,000

* This image features an undressed child.

Feature Image: Pepi Stojanovski