Jean-Michel Basquiat’s short life was, by and large, a frenetic storm of chaotic struggle and majestic creativity. Since his sad death in 1988 - aged just 27 - the reputation, stature, and legacy of this maverick American ‘street’ artist has grown and grown, gathering immense power and strength. Where the art markets are concerned, Basquiat is now an unstoppable hurricane: a genuine icon. As one the most highly valued artists in the world, much of his instantly distinctive work - most of it completed in a dizzying three-year spell between 1981 and 1984 - regularly sells at auction for tens of millions of dollars. It’s unlikely Basquiat could have envisioned phenomenal commercial success - but that’s not to say he lacked ambition, despite his rather humble beginnings. Born in Brooklyn, New York, to a Haitian father and a Puerto Rican mother, money was tight and life was hard. Nonetheless, Basquiat was a precocious child with real artistic talent emerging early on. His mother nurtured these traits, giving him a copy of Gray's Anatomy at the age of seven while he spent months recovering from a car accident – an experience that later proved to be a profound visual influence.
Rebellion drove Basquiat forward. He always sought out the alternative angle, in his spirited lifestyle and his outlook. Having dropped out of high school, he left home as a teenager and pursued a life of independence and untethered artistic expression. He first gained recognition in the late 1970s as part of the SAMO duo, scrawling cryptic graffiti around New York City. Coruscating social critiques and enigmatic poetry was integral to his street art, and it made him stand out. The canvas beckoned. With skill and abandon, Basquiat unleashed his raw, graffiti-inspired style into gallery art. Once again his boldness caught the eye – especially as the themes he was tackling (colonialism, systemic racism, personal identity) generated a grander spotlight. His 1981 collaboration with art dealer Annina Nosei and their participation in the New York/New Wave exhibition launched him into the wider art world, which desperately wanted to make sense of his work. A prime spell ensued, and he let rip with signature style – primitive imagery, bold colours, fragmented text, a tangible sense of vibrancy. Bridging the gap between high and low art is a staggering legacy: budding street artists and billionaire art collectors alike think of him as a rock star. Here is a guide to his most expensive works.
Untitled, 1982 (US$110.5m)
‘Untitled’ is quite simply one of the most iconic and expensive artworks in history. This raw, totemic painting became the most expensive Basquiat work to ever sell at auction, selling for an incredible $110.5m at Sotheby’s New York in May 2017, greatly surpassing its presale high estimate of $60m. Its trademark depiction of a skull-like face on a vivid, partially-blue background is symptomatic of Basquiat at his best – a riot of acrylic, spray paint, and oilstick, showcasing his ‘street’ style while blending neo-expressionist and graffiti-inspired elements, along with (what commentators deem to be) profound commentary on identity and power play. The skeletal face is seen as a representation of mortality and Basquiat’s African-American identity, encapsulating an almost-live ‘battle’, his inner demons and struggles writ large on the giant canvas. This work is also notable for its timing – Basquiat’s fame was on the rise, and it hadn’t actually been seen publicly since 1984, when it was bought at Christie’s by Jerry and Emily Spiegel for $19,000. When Japanese billionaire Yusaku Maezawa bought it in 2017, Basquiat’s place as one of the most critical voices in global contemporary art was truly cemented. “He’s now in the same league as Francis Bacon and Pablo Picasso,” opined specialist dealer Jeffrey Deitch.
In This Case, 1983 (US$93.1m)
Majestic, menacing, busy, delectable. This Basquiat work represents a cool $90 million dollars-plus worth of oil and canvas, all six by six feet of it. Executed at the age of 22, In This Case depicts a large skull head set against a ruby-red background, with a piercing yellow-set eye, grotesquely protruding green teeth, and a fractured, eerie, warped anatomy. Ultimately it’s a portrait of what appears to be a distressed black face: does it have a haunted expression? Does the audience find it haunting? Perhaps both. Ambiguity of interpretation was Basquiat’s playground, as per the greats, and this painting is a prime example of how he was drawn to the human head’s form, forever exploring and unravelling the face – seemingly rupturing and ripping apart its features to investigate the mystical portal between exterior physical presence and man’s hidden, often disturbing, psychological landscape. In This Case is the last in a series of large skull paintings made between 1981 and 1983, and was sold by Italian businessman Giancarlo Giammetti - co-founder of the fashion house Valentino.
El Gran Espectaculo [The Nile], 1983 (US$67m)
Less mysterious than other Basquiat works, El Gran Espectaculo (The Nile) is also known as Untitled (History of the Black People). This large triptych is quite the social and political exploration, taking the viewer on both a visual journey, and more strikingly, demanding the audience embark on some kind of introspection and inner soul-searching. Employing a mesmerising blend of iconography and symbolism, Basquiat fundamentally uses this piece as a means to address issues of representation of the African diaspora within the larger context of world history. An audacious painting, there are feverish compositions of floating skulls, along with emaciated figures and scrawled phrases that variably reference American politics and ancient Egypt. With an estimated value of $45 million, a three-way bidding battle saw the work ‘hammered’ at $58 million (rising to a final price of $67 million, with fees).
Untitled [Devil], 1982 (US$57.3m)
Snapped up by avid Basquiat collector Yusaku Maezawa, this billboard-sized painting features a demonic, skeletal figure with horns – a chaotic, visceral, disturbing vision with a dynamic colour palette dominated by reds, blacks, and yellows. Traditionally a ‘devil’ figure is interpreted as a symbol of internal struggle, societal corruption, or the darker side of human nature – and Basquiat was playing into this, no doubt, with the horns likely representing his constant critique of systemic power and authority. Again, the fragmented imagery and deep layering suggest Basquiat is unpicking the psyche, exposing his ideas of deeply multidimensional identity and a battle with morality. Despite his success, Basquiat was deeply critical of and cynical about the art world and what he saw as its commodification.
Versus Medici, 1982 (US$50.8m)
Sold during Sotheby’s marathon evening sale event in May 2021, Versus Medici was bought by mega collector and casino mogul Steve Wynn. Considered one of Basquiat’s masterpieces, this provocative work has featured in major retrospectives and exhibitions, and is viewed by an adoring art world as a bold declaration of his intent to turn art history on its head. His critique is coruscating – it features a central skeletal figure, likely representing Basquiat himself, around which are fragmented symbols, graffiti-like marks, and various words referencing the Medici family (immensely powerful ‘patrons’ of the arts during the Renaissance period). The symbolism is obvious, as per the painting’s title: Basquiat is an anti-establishment outsider fighting for recognition in a world dominated by the Western art hierarchy and its subsequent idealism. The crown shows Basquiat's evident self worth.
The cultural significance of Basquiat cannot be underestimated, set in stone by his enduring influence on art, pop culture, and even fashion. The sky-high value of his prominent works reflect this, while elevating him into the pantheon of greats. What tips the balance towards genius is his ability to break boundaries. Breaking records at auction seems entirely natural.
