
Source: Public Domain / Wikimedia Commons
20. Portrait of Adele Bloch-Bauer II, 1912
> Artist: Gustav Klimt
> Sale price: $150,000,000, date unknown, 2016
> Inflation-adjusted price: $183,332,250
This portrait of Viennese socialite Adele Bloch-Bauer is among multiple works by Klimt that were stolen from the Bloch-Bauer family by the Nazis during World War II and subsequently displayed at the Österreichische Galerie Belvedere in Vienna. In 2006, after lengthy legal battles, five Klimt canvases were returned to Bloch-Bauer’s niece, who sold this portrait to Oprah Winfrey for nearly $88 million. In 2016, Winfrey sold the painting to an anonymous Chinese collector for $150 million.

Source: ergsart / Flickr
19. Portrait of Dr. Gachet, 1890
> Artist: Vincent van Gogh
> Sale price: $82,500,000, May 15, 1990
> Inflation-adjusted price: $186,644,120
This portrait of Van Gogh’s close friend – a doctor who cared for the artist during his last months of life – set a world record in 1990 when it sold at Christie’s for $82.5 million to a Japanese art collector named Ryoei Saito. After Saito threatened to have the portrait burned alongside him after his death (along with Renoir’s “Bal du Moulin de la Galette,” which he’d also purchased), the painting quietly sold – possibly to an Italian art collector – and its whereabouts are currently unknown.
18. Portrait of Adele Bloch-Bauer I, 1907
> Artist: Gustav Klimt
> Sale price: $135,000,000, June (day unknown), 2006
> Inflation-adjusted price: $194,479,840
Another Klimt work stolen by the Nazis and eventually returned to its owner’s heir, the first “Portrait of Adele Bloch-Bauer” is the subject of a 2015 film called “Woman in Gold.” The film details the years of legal battles that Bloch-Bauer’s niece Maria Altmann (played by Helen Mirren) endured in order to reclaim the painting. Intent on the work being accessible to the public, the real-life Altmann sold the portrait to American billionaire Ronald Lauder, who placed it in the Neue Galerie in New York City.

Source: Stroud / Express / Hulton Archive / Getty Images
17. Le Rêve, 1932
> Artist: Pablo Picasso
> Sale price: $155,000,000, March 26, 2013
> Inflation-adjusted price: $194,635,460
In 2006, hedge fund manager Steven A. Cohen was set to buy this cubist portrait of Picasso’s muse and mistress from casino mogul Steve Wynn, when Wynn accidentally punctured the painting with his elbow. In 2013 – after a $90,000 restoration – Cohen finally purchased the painting from Wynn for $155 million ($134 million in 2006 dollars).

Source: Dia Dipasupil / Getty Images Entertainment via Getty Images
16. Shot Sage Blue Marilyn, 1964
> Artist: Andy Warhol
> Sale price: $195,040,000, May 8, 2022
> Inflation-adjusted price: $195,040,000
In early May of this year, this iconic Warhol portrait of Marilyn Monroe sold for $195 million at Christie’s in New York City, setting the record for the highest price ever paid for an American work of art. The silkscreen print, entitled “Shot Sage Blue Marilyn,” is one in a series of five depictions of the movie star produced by Andy Warhol in 1964. Four of the prints were damaged (and later repaired) when a guest at Warhol’s studio pulled out a gun and shot through a stack of the completed prints.
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