The Most Expensive Basquiat Paintings Are Message-Infused Masterpieces

The 15 most expensive Basquiat paintings ever sold

Ready to discover our ranking of Jean-Michel Basquiat’s most valuable paintings? Let’s dive in!

Psssst: curious to see how far things can go in the world of art? Check our list of the absolute most expensive paintings ever sold. You can also check our ranking of the most expensive Alec Monopoly paintings if you prefer something more contemporary.

Untitled (One Eyed Man or Xerox Face), 1982 – $30.2 Million

“Untitled (One Eyed Man or Xerox Face),” created in 1982 by Jean-Michel Basquiat, is a striking work that encapsulates the raw, emotive energy characteristic of Basquiat’s oeuvre. 

This painting, vivid with its bold lines and compelling imagery, showcases a singular, large-eyed figure that dominates the canvas, suggesting themes of identity, perception, and the complexities of the human psyche. 

The artwork’s alternative title, Xerox Face, hints at a critique of societal norms and the mass production of culture, emblematic of Basquiat’s ability to intertwine social commentary with deeply personal expression. 

As one of the most expensive Basquiat paintings ever auctioned, it was last sold in 2021 for $30.2 million to an anonymous buyer at Christie’s in Hong Kong. 

Flesh and Spirit, 1982–83 – $30.7 million

“Flesh and Spirit” is a monumental Jean Michael Basquiat artwork created between 1982 and 1983. Aptly named, the complex canvas intricately weaves together abstract and figurative elements, a physical exploration of corporeal existence versus spiritual transcendence.

This masterpiece, rich in symbols, text, and cryptic codes, sprawls across a vast canvas, showcasing Basquiat’s unique ability to blend raw, expressive brushwork with deeply layered meaning. 

The significant piece was last sold for $30.7 million to an anonymous buyer at a Sotheby’s auction in New York in May 2018, inviting viewers into a dialogue between material and metaphysical. 

Untitled (Tar Tar Tar, Lead Lead Lead), 1981 – $34.9 million

“Untitled (Tar Tar Tar, Lead Lead Lead),” created in 1981, is a powerful example of his early work, characterized by a raw, energetic style and profound thematic depth. 

The Basquiat painting features the artist’s signature combination of graffiti-like scribbles, symbols, and cryptic texts against a stark canvas, reflecting a visceral response to urban life and social issues. 

The repeated words “Tar” and “Lead” suggest a commentary on the industrial materials that symbolize urban decay and the toxicity of city environments, perhaps critiquing the societal neglect of marginalized communities.

This piece was last sold for $34.9 million as part of collector Anita Reiner’s estate. The sale took place at a Christie’s auction in May 2014. 

La Hara, 1981 – $35 million

“La Hara,” painted in 1981, is an arresting acrylic and oil stick Basquiat artwork on a wood panel, depicting a stark, skeletal figure that embodies the artist’s critique of authority and racial tensions. 

The title “La Hara” is a slang term for the police, derived from New York City’s Puerto Rican community, capturing Basquiat’s commentary on police presence and brutality in minority neighborhoods. This Basquiat artwork, with its haunting, red-eyed figure set against a dark background, powerfully conveys themes of surveillance, oppression, and the systemic challenges faced by people of color.

“La Hara” was sold in May 2017 at a Christie’s auction in New York to an anonymous telephone bidder for $35 million, thus cementing its place on our list of the most expensive Basquiat artworks ever sold.

The Field Next to the Other Road, 1981 – $37.1 million

“The Field Next to the Other Road,” created in 1981, is a compelling large-scale painting that delves into themes of life, death, and transition. 

This piece stands out for its dynamic composition, featuring a vibrant tableau of figures, cryptic symbols, and abstracted forms sprawled across a vast canvas. The painting’s enigmatic title evokes a sense of journey and displacement, possibly reflecting Basquiat’s contemplation on the paths and choices that define human experience.

This highly anticipated artwork was sold to an anonymous caller for $37.1 million in May 2015 at a Christie’s auction in New York.

The Guilt of Gold Teeth, 1982 – 40 Million

“The Guilt of Gold Teeth,” created in 1982 by Jean-Michel Basquiat, is a striking example of his ability to fuse historical commentary with personal symbolism. 

This piece is characterized by Basquiat’s iconic visual language, featuring a chaotic blend of text, figures, and symbols that convey a critique of wealth, power, and inequality. The painting’s title reflects a nuanced exploration of opulence and its moral implications, possibly alluding to the disparities in societal status and the burdens of material wealth.

The iconic Basquiat painting was last sold for $40 million in 2021 at a Christie’s auction in New York as one of the most expensive Basquiat paintings ever sold. 

Warrior, 1982 – $41.8 Million

“Warrior,” painted in 1982, is a commanding artwork that epitomizes the artist’s fascination with the figure of the warrior as a symbol of resistance and struggle. 

This painting features a central figure, depicted in Basquiat’s signature raw and expressive style, armed with a sword and set against a backdrop that melds cryptic symbols and abstract elements. The figure’s posture and the intensity of its gaze convey a sense of defiance and strength, reflecting Basquiat’s commentary on the fight against oppression and his exploration of black identity and heroism.

“Warrior” was sold for $41.8 million in March 2021 at a Christie’s auction in Hong Kong, marking a significant moment as one of the highest prices achieved for a Western artwork in Asia. 

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

“Self-Portrait as a Heel (Part Two),” painted in 1982 by Jean-Michel Basquiat, is a compelling artwork that delves into the complexities of the artist’s identity and public perception. 

The painting is one of Basquiat’s profound self-portraits, where he depicts himself in a dual light, referencing both his own persona and the character of a ‘heel’—a term from professional wrestling denoting a villain or antagonist. This choice of depiction is rich with irony and introspection, highlighting Basquiat’s awareness of his contentious position within the art world and society at large.

“Self-Portrait as a Heel (Part Two)” was last sold for $42 million in 2023 at a Sotheby’s auction in New York. This portentous sale underscores the enduring appeal and cultural relevance of Basquiat’s work. 

Flexible, 1984 – $45.3 Million

“Flexible,” created in 1984, is a striking Basquiat painting that showcases the artist’s shift towards more complex, multi-layered compositions during the mid-1980s. 

This piece features a powerful, elongated figure that stretches across the canvas, rendered with Basquiat’s signature blend of spontaneous, graffiti-like lines and vibrant color. The figure, possibly a representation of a griot or a storyteller, embodies flexibility in both a physical and metaphorical sense, suggesting adaptability, resilience, and the capacity to navigate diverse cultural and social landscapes.

Resonating with Basquiat’s interest in African heritage, “Flexible” was last sold for $45.3 million in May 2018 at a Phillips auction in New York. 

Dustheads, 1982 – $48.8 Million

“Dustheads,” painted in 1982, is a vibrant and dynamic masterpiece that captures the essence of Basquiat’s raw and expressive style. 

This large canvas is dominated by two frenetic figures, rendered in a riot of colors against a black background, embodying the energy and chaos of the New York City streets. The figures, with their exaggerated features and intense, wide eyes, seem to be under the influence of a hallucinatory substance, possibly referencing the term “dust” as slang for drugs. This interpretation aligns with the painting’s exploration of themes such as addiction, alienation, and the darker aspects of urban life.

“Dustheads” was sold for $48.8 million in May 2013 at a Christie’s auction in New York, marking it as one of Basquiat’s highest-selling works at the time.

Versus Medici, 1982 – $50.8 Million

“Versus Medici,” created in 1982 by Jean-Michel Basquiat, is a bold assertion of Basquiat’s place within the canon of Western art, directly challenging the legacy of the Medici family, renowned patrons of the Renaissance. 

By juxtaposing his African heritage with the European tradition, Basquiat declares the importance and relevance of Black artists in the historically white-dominated art world. The name “Versus Medici” itself is confrontational, highlighting Basquiat’s intent to question and redefine the narratives of art history.

“Versus Medici” was sold for $50.8 million in May 2021 at a Sotheby’s auction in New York. The highly publicized sale reflects the increasing recognition and valuation of Basquiat’s work in the global art market. 

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

“El Gran Espectaculo (The Nile),” painted in 1983, is distinguished by its vibrant palette, intricate details, and the way it seamlessly blends historical references with Basquiat’s unique visual language, offering a profound commentary on the interconnectedness of cultures and the enduring impact of ancient civilizations on contemporary thought.

The title, translating to “The Great Spectacle,” suggests a grand narrative unfolding, with the Nile River serving as a metaphor for the birth and continuity of civilizations. Also known as History of the Black People, this painting is rich with symbolic imagery, including references to Egyptian iconography and African heritage, underscoring Basquiat’s exploration of his own identity within the tapestry of global history.

The artwork was sold for $67.1 million in 2023 at Christie’s, marking a significant milestone in the appreciation and valuation of Basquiat’s art.

Untitled (Devil), 1982  – $85 Million

“Untitled (Devil),” painted in 1982, is a riveting masterpiece that delves into themes of power, temptation, and the dichotomies within human nature. 

This work features a dominant, devil-like figure amidst Basquiat’s signature chaotic blend of abstract and figurative elements, rendered in a stark, compelling palette. The figure, depicted with horns and surrounded by Basquiat’s frenetic scribbles and symbols, stands as a potent symbol of the artist’s confrontation with inner demons and societal evils.

The painting was sold for $85 million in May 2022, at the Phillips’ 20th Century & Contemporary Art Evening Sale in New York. 

In this case, 1983 – $93.1 Million

“In This Case,” created in 1983, is a testament to Basquiat’s mastery in conveying complex themes through his unique visual language, drawing on personal experience, cultural heritage, and critical commentary to challenge and engage viewers.

This vibrant painting features a skull, a recurring motif in Basquiat’s work, rendered in a powerful, confrontational manner against a bright red background. The skull, while a symbol of death, is infused with life through Basquiat’s dynamic brushwork and the addition of color, text, and symbolic elements, reflecting on the fragility of life and the inevitability of death. The title itself, enigmatic and open-ended, invites interpretation and underscores the depth of inquiry present in Basquiat’s art.

This artwork was last sold for $93.1 million in May 2021 at a Christie’s auction in New York. 

Untitled, 1982 – $110.5 Million — The most expensive Basquiat ever sold

As one of the most expensive paintings sold by an American artist, “Untitled,” created in 1982, represents the pinnacle of Jean-Michel Basquiat’s exploration of identity, expression, and the human condition. 

This iconic painting features a skull – a motif that recurs throughout Basquiat’s oeuvre – set against a vibrant blue background. The skull, rendered in a dynamic and raw style, is both a contemplation of mortality and a powerful assertion of presence. This work combines elements of graffiti with anatomical sketches, highlighting Basquiat’s unique ability to bridge the gap between street art and fine art and to infuse his pieces with profound philosophical questions.

The skull painting was last sold for $110.5 million in May 2017 at a Sotheby’s auction in New York, making it the most expensive Basquiat painting ever sold. The buyer was Japanese billionaire and art collector Yusaku Maezawa.