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The Most Expensive Artworks That Celebrities Own

Sir Elton John – “Glass Tears” by Man Ray ($166K)

He may have mispronounced the name of the city he was playing at during his 2022 Kansas City T-Mobile Center center, but all is forgiven when you’re the one-and-only Sir Elton John! In addition to being one of the most prolific singer-songwriters of the 20th century, the “Tiny Dancer” singer is also an avid collector of high-end art, with a particular taste for modernist photography.

John’s extensive collection was even featured at Tate Modern, in an exhibition titled “The Radical Eye: Modernist Photography from the Sir Elton John.” His most precious piece? Man Ray’s “Glass Tears,” which he bought for roughly $166K at a 1993 Sotheby’s auction.

Kanye West & Kim Kardashian – “Roden Crater” by James Turrell ($10 Million)

Now divorced, Kanye West and Kim Kardashian once reigned as one of the world’s most influential power couples. In 2022, Kanye praised Kim’s newest Vogue cover appearance, showing there’s no bad blood between the two. And while every Kardashian photoshoot is an artwork in itself, it’s still no match to Kanye and Kim’s outstanding art collection.

The ex-couple often collaborated with high-end artists such as Kerry James Marshall, George Condo, and Jurgen Teller. Yet perhaps the crown jewel of their art collection is Kanye’s $10 million acquisition of an ambitious artwork by James Turrell. The breathtakingly conceptualized piece, titled “Roden Crater,” is set on the top of an extinct volcano!

Sean “Diddy” Combs – “Past Times” by Kerry James Marshall ($21.1 Million)

In 2022, the American rapper/record producer Sean “Diddy” Combs sold his Toluca Lake home for $6.5 million. While the sum is impressive, it’s pennies when compared to the astounding amount the “Bump Bump Bump” singer invested in acquiring “Past Times,” a painting by the celebrated American artist Kerry James Marshall.

Said to be quite an avid art collector, Combs came across the piece at an auction of Marshall’s catalog. After outbidding all his competitors who also wanted the painting by one of the best African-American painters of all time, Combs finally walked away with his prize. The price tag? An eye-watering $21.1 million!

Oprah Winfrey – “Adele Bloch-Bauer II” by Gustav Klimt ($87.9 Million)

The producer of the 2022 TV series “Kings of Napa,” Oprah Winfrey collected an astounding fortune by working for decades as one of the most-beloved TV hosts in the United States. The former “The Oprah Winfrey Show” host used some of her money to acquire a legendary Gustav Klimt painting for an unbelievable $87.9 million.

But if you think Oprah overpaid for Klimt’s iconic “Adele Bloch-Bauer II” portrait, you may be in for a surprise… After all, she ended up selling the artwork to an unknown Chinese art collector for $150 million in 2017. Now that’s how you turn a huge profit in the art market!

Swizz Beatz & Alicia Keys – “An Assistance of Amber” by Lynette Yiadom-Boakye ($500K)

Recently featured in a 2022 episode of “RuPaul’s Drag Race,” the American singer Alicia Keys has been married to the American record producer Swizz Beatz since 2010. More than two music giants, Keys and Swizz Beatz make for one of the most powerful African-American couples in the world. So it makes sense that their pushing for the appreciation of African-American art.

Keys and Swizz Beatz are said to have a huge art collection, and one of their standout pieces is the painting “An Assistance of Amber,” by the British painter/writer Lynette Yiadom-Boakye. They invested a reported $500K to get their hands on the piece.

Sir Elton John – “Glass Tears” by Man Ray ($166K)

He may have mispronounced the name of the city he was playing at during his 2022 Kansas City T-Mobile Center center, but all is forgiven when you’re the one-and-only Sir Elton John! In addition to being one of the most prolific singer-songwriters of the 20th century, the “Tiny Dancer” singer is also an avid collector of high-end art, with a particular taste for modernist photography.

John’s extensive collection was even featured at Tate Modern, in an exhibition titled “The Radical Eye: Modernist Photography from the Sir Elton John.” His most precious piece? Man Ray’s “Glass Tears,” which he bought for roughly $166K at a 1993 Sotheby’s auction.

Cheech Marin – Chicano Art ($9.7 Million)

Best known for being half of the comedy act “Cheech & Chong,” the American comedian Cheech Marin launched a new brand of nationwide meals for marijuana lovers in 2022. A bonafide stoner icon, Cheech is also the owner of one of the world’s most impressive private collections of Chicano art (i.e., art created by Mexican-American artists).

His collection includes artworks by painters such as Carlos Almaraz, Gronk, and Gilbert Lujan. And while the value of Cheech’s acquisitions was never made public, his Chicano art museum—The Cheech Marin Center for Chicano Art—was once given an impressive $9.7 million by the state of California!

Madonna – “Buste de Femme á la Frange” by Pablo Picasso ($5 Million)

In 2022, the pop superstar Madonna made the news after publishing a revealing picture of herself on Instagram. It goes to show that the “Material Girl” singer is still pushing the envelope, and the same can be said of her outstanding art collection. According to The Talko, she invested about $100 million in high-end art over the years!

Madonna’s impressive collection includes artworks by some of the most renowned artists of the 20th century, including the Mexican painter Frida Kahlo and the legendary Jean-Michel Basquiat. The pièce de resistánce, however, is Pablo Picasso’s “Buste de Femme á la Frange,” which she bought for $5 million at an art auction.

Anderson Cooper – “Portrait of Mariana de Silva y Sarmiento, Duquesa de Huescar” by Anton Raphael Mengs ($275K)

Featured in 2022 episodes of “Anderson Cooper 360º” and “60 Minutes,” Anderson Cooper is one of the most beloved TV personalities in the United States. The New York City native is also said to be an avid collector of art, and he’s not afraid to splash some serious cash to buy the pieces he likes the most.

In 2016, for example, Cooper visited TEFAF’s Met Breuer Show in New York and fell in love with “Portrait of Mariana de Silva y Sarmiento, Duquesa de Huescar,” an unfinished work by the 18th-century artist Anton Raphael Mengs. The painting—showing a woman with no face—cost him a reported $275K.

Steve Martin – “Hotel Window” by Edward Hopper ($10 Million)

In 2022, the “Only Murders in the Building” co-stars Steve Martin and Martin Short announced a series of shows on the Las Vegas Strip. A comedy icon, Martin knows exactly what it takes to be successful in show business; but did you know he has the same prowess for turning a profit at the high-end art market?

That’s right: in addition to having a massive art collection, Martin has made a few savvy moves in the art world. In 1999, for instance, he bought Edward Hopper’s “Hotel Window” oil painting for $10 million, only to sell it for $26.5 million seven years later!

John McEnroe – “Helter Skelter I” by Mark Bradford ($10.4 Million)

Featured in 2022 episodes of the TV series “Never Have I Never,” John McEnroe is a legendary former tennis player and occasional actor. This West Germany native also loves to play in the art market, and he never shies away from turning a hefty profit—even if he does so with an artwork inspired by the infamous serial killer Charles Manson.

In 2007, McEnroe bought Mark Bradford’s Manson-inspired “Helter Skelter I” for an undisclosed amount, only to sell it for an astounding $10.5 million at a 2018 Phillips auction in London. The painting is 34-foot-wide and makes for an expressionist masterpiece in the line of Jackson Pollock.

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