The Most Expensive Artworks That Celebrities Own

TrendingAugust 10, 2022

John Waters – Andy Warhol, Roy Lichtenstein & Others (Undisclosed)

Featured in a 2022 episode of “Search Party,” the cult filmmaker/actor John Waters is an art collector with a taste for the ugly and bizarre. Nicknamed “The Pope of Thrash,” he once donated hundreds of artworks to the Baltimore Museum of Art and was given a very appropriate honor in return: he had one of the museum’s bathrooms named after him!

Even though Waters loves to amass pieces as unusual as monkey art (art made by monkeys) and thrash-filled table installations, he also has a few pricy gems in his collection, including paintings by the renowned Pop-Art geniuses Andy Warhol and Roy Lichtenstein.

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.

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!

Ellen DeGeneres & Portia de Rossi – “Ovine Sheep Pieces” by François-Xavier Lalanne ($1 Million)

Featured in the 2022 documentary “Celebrating Betty White: America’s Golden Girl,” the TV host Ellen DeGeneres is said to be an avid art collector. Ellen and her wife Portia de Rossi invested millions in pieces made by artists as renowned as Diego Giacometti and Ruth Asawa. But in 2020, the power couple decided to auction off $10 million worth of artwork from their private collection.

The auction’s standout artwork was “Ovine Sheep Pieces,” a series of sheep sculptures produced by François-Xavier Lalanne that outlets such as Mirror described as “bizarre.” Lalanne’s high-end sheep retail from 500K to as much as $1 million apiece.

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.

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.

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!

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.

Beyoncé & Jay Z – “Mecca” by Jean-Michel Basquiat ($4.2 Million)

Beyoncé and Jay-Z: can you think of a more classy celebrity couple? In 2022, the two musicians made the shortlist for Best Original Song at the Oscars, proving once again that they’re still sitting at the top of the world! With a reported combined net worth of $1.9 billion, this American power couple gets to have a collection of everything expensive, from million-dollar vehicles to massive mansions. And high-end art, of course, is no exception.

In 2013, Jay-Z visited a Sotheby’s auction and splashed $4.2 million to buy “Mecca,” a famous painting by Jean-Michel Basquiat showcasing the New York City landscape with the word ‘Empire’ on top.

Leonardo DiCaprio – “Double Gray Scramble” by Frank Stella ($1 Million)

One of the stars of the 2022 drama “Killers of the Flower Moon,” the renowned American actor Leonardo DiCaprio seems to have a genuine love for art. He visits art auctions regularly and, unlike other celebs, he seldom goes for the most expensive piece. Instead, he’s carefully selected an eclectic collection of works by artists as distinctive as cartoonist Robert Crumb, abstract painter Oscar Murillo, or modern-day artist Jean-Pierre Roy.

DiCaprio’s art acquisitions often top the hundreds of thousands of dollars, but Frank Stella’s 1973 geometric masterpiece “Double Gray Scramble” is one of the few that cost him a reported $1 million.

Ed Sheeran – “Dab 2” by Ed Sheeran ($52K)

In 2022, the chart-topping singer Ed Sheeran announced the release of “The Joker and The Queen,” a song featuring American country-music favorite Taylor Swift. Known for his modest and laidback attitude, Sheeran is arguably one of the world’s most likable millionaires. And while he’s not particularly known for spending millions on art, he’s highly involved with the high-end art world.

For one, he was once painted by the legendary English artist David Hockney! In addition, he became an artist himself in 2020, when he sold his Jackson Pollock-inspired painting “Dab 2” for an impressive $52K at a charity auction.

Pharrell Williams – “The Simple Things” by Pharrell Williams & Takashi Murakami ($2.6 Million)

There’s no stopping Pharrell Williams: the renowned music producer joined forces with Justin Timberlake in 2022 to invest in a $620-million online security company, all while designing a line of diamond sunglasses for Tiffany! Needless to say, Williams can do it all, including collaborating with his favorite artist in the world…

That’s right: an avid collector of the artworks of the vibrant Japanese artist Takashi Murakami, Williams was given the chance to work with the man himself to create the 2019 sculpture “The Simple Things.” According to The Value, the wonky sculpture was estimated to be worth a minimum of $2.6 million.

Tom Ford – “Self Portrait” by Andy Warhol ($32.6 Million)

While Tom Ford has sadly decided to cancel his much-anticipated 2022 New York Fashion Week show, he’s still one of the most influential and renowned designers in the world. As a man who defines taste, Ford is unsurprisingly a man of good taste himself, and he’s said to have an impressive art collection featuring works by Mark Bradford, Sam Taylor Wood, and others.

He also used to own a famous “Self Portrait” piece by the Pop-Art legend Andy Warhol, but he decided to sell it for a staggering $32.6 million! Years later, he made the news after spending $90K to buy a black dress designed by… Tom Ford.

David Beckham & Victoria Beckham – “Daddy’s Girl” by Damien Hirst ($813K)

In 2022, David Beckham surprised the world when he revealed that his wife Victoria has eaten the same meal for 25 years! Luckily, the portfolio of assets of the Beckhams (worth a combined $1 billion) is more diversified than Victoria’s eating habits, and it even includes an $813K artwork by Damien Hirst.

In 2014, the Beckhams attended an art auction and fell in love with Hirst’s “Daddy’s Girl” piece, comprised of a single pink heart covered with a few colorful butterflies. An avid art collector himself, Hirst is reported to be the richest living artist in the United Kingdom.

Neil Patrick Harris – Gideon Rubin Painting ($28K)

Starring in the 2022 comedy “The Unbearable Weight of Massive Talent,” actor Neil Patrick Harris is said to be an avid art collector. Harris and his partner David Burtka own artworks by people as renowned as Ahmed Alsoudani, Ed Ruscha, or Kehinde Wiley. But their favorite artist has got to be the contemporary Israeli painter Gideon Rubin.

How much do they like Rubin, you wonder? Well, for one, they named their son after him! Needless to say, they have at least one Rubin painting back home. While the name and price of the artwork were never disclosed, Rubin’s best pieces sell for approximately $28K each.

Sofia Coppola – “Cold Beer Beautiful Girls” by Ed Ruscha ($60K)

Renowned filmmaker and director of the 2021 short “New York City Ballet,” Sofia Coppola considers herself an artist first and foremost. She also loves collecting art, though she has a different reason for it than some of her peers. Coppola doesn’t buy art as an investment but because she loves incorporating her finds into her movie sets.

She talked about her relationship with art with Artspace in 2016 and mentioned Tina Barney, Richard Prince, and Ed Ruscha as go-to sources of inspiration. For instance, in her office, Copolla proudly displays a print of Ruscha’s “Cold Beer Beautiful Girls.” The original is estimated to be worth approximately $60K.

Lady Gaga – Michael Jackson’s “Bad” Jacket ($240K)

In 2022, the American singer/actress Lady Gaga announced the return of her ‘Jazz & Piano’ Las Vegas residence. Reported to be a fan of artists such as Francesco Vezzoli and Leigh Bowery, the “Bad Romance” singer likes to spend her money on more than just high-end artworks. After all, she once bought a diamond-encrusted iPad and a $50K ghost detector machine!

But guess what? As a bonafide fan of the late Michael Jackson, Gaga invested several hundred thousand dollars in a $5-million collector’s auction dedicated to the King of Pop. She reportedly bought Jackson’s iconic jacket from the “Bad” album tour for a whopping $240K.

Brad Pitt & Angelina Jolie – “Tower of the Koutoubia Mosque” by Winston Churchill ($11.5 Million)

Featured in a 2022 episode of the TV series “Dish Nation,” Angelina Jolie was once the owner of a painting that’s as rare as it is historical. “The Tower of the Koutoubia Mosque” was painted by none other than the iconic British politician Winston Churchill and gifted to the former American President Franklin Roosevelt on the occasion of an official 1943 visit to Morocco.

The precious painting was later bought by Brad Pitt and given to Jolie as a present. Considering that Pitt and Jolie filed for divorce in 2016, it’s no surprise that the “Maleficent” star decided to sell the artwork for a reported $11.5 million in 2021.

Grant Hill – The Grant Hill Collection of African American Art (Undisclosed)

The author of the 2022 memoir “Game,” Grant Hill is a former basketball player best known for being the co-owner of the Atlanta Hawks. No stranger to the world of publishing, Hill once helped to give life to the paperback book “Something All Our Own: The Grant Hill Collection of African American Art.”

The book featured prints of the extensive collection of African American artworks that Hill and his wife Janet amassed over the years. While the collection’s value was never disclosed, the Hills played a pivotal role in the recent appreciation of African American art in the high-end art market.

Tobey Maguire – “Tincture” by Mark Rylen ($42.5K)

One of the stars of the 2022 TV series “Extrapolations,” the “Spider-Man” actor Tobey Maguire is known for being a savvy real estate investor and a prolific amateur poker player. But Maguire’s hobbies also include betting on the art market, as reported by the website Widewalls.

Maguire’s art acquisitions have been pretty discreet, but the Santa Monica, California native is said to be a big fan of the Japanese artist Kaz Oshiro. Additionally, he once splashed $42.5K in “Tincture,” a painting by the obscure artist Mark Rilen, bought during MOCA’s annual FRESH silent auction.

Mary-Kate Olsen & Ashley Olsen – Works by Jean-Michel Basquiat, Man Ray & Andy Warhol (Undisclosed)

In 2022, the Olsen sisters made the news for their passionate tribute to the late Bob Saget. Years before, the two socialites were the subject of a TheArtGorgeous website article that focused on their intimate relationship with the art world. Mary-Kate and Ashley have attended multiple exhibitions, inspired famous artworks, and even dated art dealers such as Richard Sachs!

Additionally, they’re reported to have an incredible art collection. Little is known about it, but they’re rumored to own pieces from artists as renowned as Jean-Michel Basquiat, Man Ray, and Andy Warhol.

Eric Clapton – “Abstraktes Bild (809-4)” by Gerhard Richter ($34 Million)

In 2022, the guitar virtuoso Eric Clapton made headlines all over the world after comparing vaccinated people to victims of “mass hypnosis.” And while you may find this controversial remark to be, erm, underwhelming, you’ll certainly have to agree that Clapton knows how to turn a profit in the art market. And by profit, we mean selling art for ten times the price he originally paid for it!

In 2012, Rolling Stone magazine reported that Clapton sold his “Abstrakets Bild (804-9)” painting by Gerhard Richter for a whopping $34 million at a Sotheby’s auction. Remarkably, Clapton bought the painting for a “mere” $3.4 million in 2001.

Moby – Eclectic Art Collection (Undisclosed)

Promoting the 2022 album “Reprise Remixes,” Moby is a famous electronic music producer currently residing in Los Angeles. The author of the cult 1999 album “Play,” he’s said to be an eclectic artwork collector. Shepard Fairey and Mark Ryden are some of his favorite high-end artists, but he also has a few other surprising items back home.

Moby reportedly owns drawing by “The Simpsons” creator Matt Groening and a few pieces made by the surrealist filmmaker David Lynch. It’s uncertain whether he acquired his artworks at an auction or dealt privately with the artists, and the value of his collection was never disclosed.

Rainn Wilson – Works by Robert Wilson & Others (Undisclosed)

Featured in 2022’s “Dark Winds,” the American actor Rainn Wilson is best known for portraying the goofball character of ‘Dwight’ in “The Office.” But did you know that Rainn is the son of the American painter Robert Wilson? In an Architectural Digest video, he proudly exhibited one of the last pieces ever made by his father.

In the video, Rainn and his wife—writer Holiday Reinhorn—also exhibited a few items of their vast Asian art collection, as well as a couple of paintings made by contemporary artists. Rainn even shared an anecdote about an edgy Joe Sola painting titled “Me’n Kippenberger.”

John Waters – Andy Warhol, Roy Lichtenstein & Others (Undisclosed)

Bill Koch – “La Gommeuse” by Pablo Picasso ($67.45 Million)

Making billions by distributing oil can give you a bad rep, but the American businessman Bill Koch was actually mentioned in Forbes magazine’s list of 25 top philanthropists of 2022. With an eye-watering net worth of $2.2 billion, Koch made headlines in the art world in 2015, when he sold his Pablo Picasso “La Gommeuse” painting for an astounding $67.45 million.

Koch bought the painting for “just” $3 million in the mid-’80s and only then discovered that the canvas featured a second Picasso artwork in the back! The Koch Industries magnate got lucky and ended up landing one of the most profitable art-market deals in recent history.

Val Kilmer – “Tumbleweed” by Val Kilmer ($150K)

One of the stars of the 2022 blockbuster “Top Gun: Maverick,” Val Kilmer is a renowned American actor. The Los Angeles native is also an artist, even though his explorations into the art world haven’t been nearly as successful as his career in the movies. To understand what we mean, it’s necessary to take a look at his most famous artwork: “Tumbleweed.”

“Tumbleweed” is a sculpture of a golden tumbleweed that Kilmer was once selling for $150K. While the sculpture itself raised some eyebrows, the real problems started when an artist called Bale Creek Allen accused the “The Saint” star of copying his work.

Jane Holzer – “Untitled (Cowboy)” by Richard Prince ($585K)

Interviewed by Palm Beach Illustrated in late 2021, the American model Emma Holzer talked about how she was inspired by her grandmother, the American art collector Jane Holzer. Before buying and selling high-end artworks, Jane was known for being one of the muses of Andy Warhol.

In addition to collecting art, Jane also keeps busy renovating luxury homes. Among the most valuable works in her collection is “Untitled (Cowboy),” a piece by Richard Prince that was inspired by a Marlboro ad. The artwork cost her a reported $585K but ended up being at the origin of a lawsuit filed by Jane against Lower East Side Gallery in 2013.

Danny Simmons – “Miles to Go B4 I Sleep” by Danny Simmons ($25K)

The older brother of the hip-hop record executive Russell Simmons and the rapper Joseph Simmons (of “Run D.M.C.” fame), Danny Simmons is a New York-based artist/poet with a Peabody Award in the bag. In addition to being a famous painter, he collaborates extensively with philanthropic programs, often helping disadvantaged youngsters to access art and education.

One of the creators of HBO’s “Def Poetry Jam,” Danny is arguably Brooklyn’s most influential grassroots art promoter. Some of his paintings are still up for sale, including “Miles to Go B4 I Sleep,” listed for $25K.

Marc Jacobs – “Soothsayer” by Jean-Michel Basquiat ($1.06 Million)

In 2022, a glitch on the Marc Jacobs website discounted pricey bags by 100%. A few lucky shoppers got their hands on a few free bags, but Jacobs—who’s one of the world’s most renowned fashion designers—is expected to survive the mishap. With a net worth of $200 million, he’s said to be an avid art collector.

In 2019, his collection was put up for sale at a Sotheby’s auction in New York, and there were a few impressive pieces in there. The standout artwork was Jean-Michel Basquiat’s “Soothsayer,” evaluated at a little over $1 million. Jacobs also listed works by artists as acclaimed as Ed Ruscha and Jeff Koons.