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From Street Art to Stardom: Most Expensive Basquiat Paintings of All Time

Jean-Michel Basquiat’s legacy as one of the 20th century’s most influential artists is undeniable. Emerging from the Brooklyn streets in the 1980s, Basquiat’s vibrant artworks employed bold colors, expressive brushstrokes, and a compelling mix of imagery. Influenced by his Haitian and Puerto Rican heritage, Basquiat’s vibrant artworks wove a rich tapestry of the human experience. Through bold colors, expressive brushstrokes, and evocative themes, he confronted issues of race, identity, and social injustice. His bold and thought-provoking works continue to captivate audiences and collectors alike, with many fetching astronomical sums at auction. We delve into Basquiat’s most lucrative works, testaments to his enduring influence on the art world.

10. The Guilt of Gold Teeth, 1982 – 40 Million

The Guilt of Gold Teeth
Jean-Michel Basquiat, The Guilt of Gold Teeth (1982) – Photo: Christie’s

Basquiat’s ‘The Guilt of Gold Teeth’ (1982) is one of eight paintings he created in Modena, Italy. This large-scale work portrays Baron Samedi, a powerful figure in Haitian Vodou who presides over death and the afterlife. Baron Samedi is often depicted with a top hat and skull-like features, as seen in Basquiat’s artwork. The iconic Basquiat painting fetched a record-breaking $40 million in November 2021 at Christie’s 21st Century Art Evening Sale in New York.

9. Warrior, 1982 – $41.8 Million

Jean-Michel Basquiat, Warrior
Jean-Michel Basquiat, Warrior(1982) – Photo : Christie’s

The “Warrior” painting by Jean-Michel Basquiat fetched $41.8 million at Christie’s auction in Hong Kong, marking it as the most expensive Western work of art ever sold in Asia, according to the auction house. Created in 1982, a peak year for Jean-Michel Basquiat, “Warrior” is a powerful artwork on wood (183 x 122 cm, 72 x 48 in). Executed in acrylic and spray paint, the work portrays a formidable warrior brandishing a silver sword. This piece, while not a traditional street work, retains a sense of Basquiat’s signature rawness and spontaneity.

8. Self-Portrait as a Heel (Part Two),1982 – $42 Million

Jean-Michel Basquiat, Self-Portrait as a Heel 1982
Jean-Michel Basquiat, Self-Portrait as a Heel (Part Two),1982 – Photo: Sotheby’s

One of Jean-Michel Basquiat’s few self-portraits – this artwork was created in 1982 during his residency in Los Angeles, a period marked by prolific creativity. Standing at 8 feet tall, it was specifically crafted for his inaugural West Coast exhibition at the Gagosian Gallery in L.A. Rendered in hues of green, black, beige, and blue, the piece offers a captivating glimpse into Basquiat’s artistic expression during this time. Estimated at $40-60 million USD, Jean-Michel Basquiat’s ‘Self-Portrait as a Heel (Part Two)’ sold for $42 million at a Sotheby’s auction in New York in 2023.

7. Flexible, 1984 – $45.3 Million

Jean-Michel Basquiat, Flexible
Jean-Michel Basquiat, Flexible, 1984 / Photo: Phillips

When Jean-Michel Basquiat was asked to define his art, he answered without hesitation “royalty, heroism, and the streets.” This is the essence of “Flexible,” 1984. In numerous aspects, this artwork embodies a culmination of three core themes. Basquiat portrays a tribal king figure, whose stance, with arms raised and interlocked above his head, exudes confidence and authority, emblematic of heroism. It appears as though he is crowning himself. The context of the picture’s creation, along with the support it receives, harks back to the artist’s roots on the streets of Manhattan. The artwork, measuring 102 x 75 in. (259.1 x 190.5 cm), was initially estimated to fetch between $20 million to $30 million. However, it significantly surpassed this range through consistent bidding. Eventually, it was sold to a phone bidder for $40 million, achieving a total of $45.3 million including the premium, during the auction held on May 17th, 2018, in New York.

6. Dustheads, 1982 – $48.8 Million

Jean-Michel Basquiat, Dustheads
Jean-Michel Basquiat, Dustheads, 1982 / Photo: Christie’s

Created in 1982, ‘Dustheads’ exemplifies Jean-Michel Basquiat’s raw and expressive style. This vibrant and dynamic canvas portrays two gaunt figures, possibly drug addicts, amidst a riot of color against a stark black backdrop. The scene pulsates with energy, leaving the viewer to contemplate the figures’ story and the chaotic beauty of New York City streets. In May 2013, Malaysian businessman Jho Low purchased it for a record-breaking $48.8 million at Christie’s, marking the highest price ever paid for a Basquiat painting at auction at that time.

5. Versus Medici, 1982 – $50.8 Million

Jean-Michel Basquiat, Versus Medici
Jean-Michel Basquiat, Versus Medici, 1982 / Photo: Sotheby’s

‘Versus Medici’ (1982) is a testament to Jean-Michel Basquiat’s artistic genius, created when he was just 22. This symbolic work represents a bold challenge to the Western art establishment. Basquiat crowns himself the heir to the artistic legacy of the Italian Renaissance masters, sparking a dialogue about power and representation in the art world. Jean-Michel Basquiat’s “Versus Medici” fetched $50.8 million USD at Sotheby’s in May 2021, exceeding its $50 million USD pre-sale estimate.

4. El Gran Espectaculo (The Nile), 1983 – $67.1 million

Jean-Michel Basquiat, El Gran Espectaculo
Jean-Michel Basquiat, El Gran Espectaculo (The Nile), 1983 / Photo: Christie’s

Painted in 1983, Jean-Michel Basquiat’s ‘El Gran Espectaculo (The Nile)’—also known as ‘Untitled (History of the Black People)’—draws connections between Ancient Egypt and the Southern United States. This thought-provoking work challenges Western historical narratives and their tendency to overlook the legacy of slavery. Once part of fashion designer Valentino Garavani’s collection, the painting fetched a remarkable $67.1 million when it went under the hammer at Christie’s in May 2023.

3. Untitled (Devil), 1982 – $85 Million

Jean-Michel Basquiat, Untitled (Devil)
Jean-Michel Basquiat, Untitled (Devil), 1982 / Photo: Phillips

In 2022, a large-scale Basquiat masterpiece, simply titled “Untitled, 1982,” fetched a staggering US$85 million at Phillips‘ 20th-Century & Contemporary Art Evening Sale. Previously owned by Japanese entrepreneur Yusaku Maezawa, this 1982 work measures an impressive 238.7 x 500.4 cm, making it one of Basquiat’s largest paintings. It belongs to a series he created during his time in Modena, Italy.

“I don’t think about art while I work. I try to think about life.” —Jean-Michel Basquiat

2. In this case, 1983 – $93.1 Million

Jean-Michel Basquiat, In this case
Jean-Michel Basquiat, In this case, 1983 / Photo: Christie’s

A culmination of Basquiat’s skull paintings (1981-1983), ‘In This Case’ is a monumental work (6ft x 6ft) featuring a skull against a vibrant red backdrop. Its fierce gaze, green teeth, and fragmented form embody Basquiat’s signature style. The piece sold for a staggering $93.1 million at Christie’s New York in May 2021, ranking second-highest among Basquiat’s works.

1. Untitled, 1982 – $110.5 Million

Jean-Michel Basquiat, Untitled, 198
Jean-Michel Basquiat, Untitled, 1982 / Photo: Sotheby’s

A crowning achievement of Jean-Michel Basquiat’s career, an untitled skull painting featuring a monumental figure against calming blues, fetched an unprecedented $110.5 million at a Sotheby’s auction in New York in May 2017. This historic acquisition solidified its status as the priciest Basquiat masterpiece ever sold, landing in the collection of Japanese billionaire and art aficionado Yusaku Maezawa.

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