Crown the Kings: Five Defining Works from Basquiat's Brief But Brilliant Career

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This post is Part 2 of our exclusive 3-part Basquiat artist series.
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Basquiat-inspired artwork by Johnny Blanco. Image courtesy of Wikimedia Commons.

📌 Pin this: Five iconic Basquiat paintings—explained for art lovers, Frame TV fans, and digital collectors.

Jean-Michel Basquiat's artistic career burned with extraordinary intensity, spanning just a single decade from his emergence in the late 1970s to his untimely death in 1988 at the age of 27. In that brief period, he produced approximately 1,000 paintings and 2,000 drawings, moving from subway graffiti to international acclaim with breathtaking speed. Basquiat’s meteoric career, though tragically brief, permanently altered the course of American art and set records at auctions around the globe [see Basquiat's auction results at Sotheby’s].

While Basquiat's visual style—which we explored in Part 1 of this series—gives his overall body of work cohesion, individual paintings reveal remarkable diversity in subject matter, emotional tone, and compositional approach. Each major work offers a window into Basquiat's evolving artistic vision and the themes that dominated his thinking.

In this second installment of our series, we'll examine five defining works that represent pivotal moments in Basquiat's artistic development and showcase the unique power of his creative voice. These paintings demonstrate how the stylistic elements we've discussed—raw expressionism, text integration, symbolic language, bold color, and cultural fusion—came together in specific works that cemented his reputation as one of the most important artists of his generation.

Untitled (Skull), 1981: The Breakthrough Self-Portrait

One of Basquiat's earliest and most iconic canvases, commonly referred to as Skull, represents his explosive entrance into the fine art world. Created for his debut solo exhibition in 1981, this painting features a large, patchwork skull against a frenetic background of splattered color and scribbled lines. Today, the original Untitled (Skull) is part of the permanent collection at The Broad in Los Angeles, one of the largest public holdings of Basquiat’s work [see The Broad’s Untitled (Skull)].

The skull itself appears to be constructed from fragmented pieces—almost like a dissection or an anatomical cross-section. With flesh, teeth, and eye sockets exposed in vibrant blues, reds, and yellows against stark black outlines, the skull has a bruised, battered appearance that implies violence or trauma. The jagged lines and expressionistic brushwork create a sense of barely contained energy, as if the head might burst apart at any moment.

Art historians often interpret this piece as a form of self-portrait—Basquiat filtering the traditional memento mori (reminder of death) through his distinctive graffiti-punk sensibility. The painting immediately signals Basquiat's interest in anatomical imagery, which would become a recurring theme throughout his career.

What makes Untitled (Skull) so remarkable is how fully formed Basquiat's visual language appears even at this early stage. The raw energy, bold contrasts, anatomical focus, and graffiti influences that would define his later work are already present, announcing the arrival of a powerful new voice in contemporary art. Collectors today can enjoy this energy through Jean-Michel Basquiat digital art downloads—modern, museum-quality digital wall art for Frame TV.

Charles the First, 1982: Crowning Black Excellence

Created during Basquiat's artistic peak in 1982, Charles the First stands as one of his most significant tributes to Black musical genius. This triumphant triptych honors jazz saxophonist Charlie Parker, illustrating Basquiat's practice of "crowning" his artistic heroes. MoMA in New York houses several Basquiat masterworks [see MoMA’s Basquiat collection]—a testament to his enduring impact on the global art scene.

Across the canvas, Basquiat scrawled phrases like "MOST YOUNG KINGS GET THEIR HEADS CUT OFF" (with the word "young" crossed out) and placed a crown above the name "Charlie Parker." The painting layers text and imagery to celebrate Parker's bebop innovations while simultaneously lamenting the premature deaths of young Black icons—a fate Basquiat himself seemed to anticipate.

The work's title carries multiple meanings. It references Charlie Parker's nickname "Bird" (Charles was his given name), but also alludes to the executed English monarch Charles I—reinforcing the painting's theme of brilliant lives cut short. Various symbols and text fragments related to Parker appear throughout the composition: musical references, biographical details, and cryptic personal associations that create a complex portrait not just of the musician, but of Basquiat's relationship to Parker's legacy.

Charles the First exemplifies Basquiat's fusion of homage and social commentary. Through his distinctive text-image synthesis, he elevates a jazz pioneer to royal status while critiquing the systems that often destroy Black brilliance. The painting's cultural resonance has extended far beyond the art world—the phrase "Most Young Kings Get Their Heads Cut Off" famously inspired rapper Jay-Z's song "Most Kingz," demonstrating how Basquiat's words continue to resonate decades later. This is why the abstract crown motif art remains a favorite among Frame TV collectors.

Horn Players, 1983: The Jazz Symphony in Paint

A dynamic triptych painted on wood panels, Horn Players represents one of Basquiat's most comprehensive tributes to his jazz influences. This vibrant work pays homage to two of his musical idols: saxophonist Charlie Parker and trumpeter Dizzy Gillespie.

The left and right panels feature crude, energetic renditions of Parker and Gillespie, while the center panel contains dense, handwritten text. Throughout the canvas, Basquiat has splashed repeated words associated with these musicians: "DIZZY," "ORNITHOLOGY" (a Parker composition), "PREE" and "CHAN" (names of Parker's daughter and wife), scattering these like musical notes across the composition.

The background alternates between broad swaths of white and black, creating a chalkboard-like effect that enhances the improvisational feel of the work. Musical annotations and the word "TEETH" (possibly referring to the musicians' embouchure or perhaps Parker's nickname "Bird" via "birdseed" teeth) add layers of personal symbolism.

What makes Horn Players exceptional is how perfectly its structure mirrors its subject. Just as jazz relies on improvisation within framework, Basquiat's composition balances chaotic energy with careful organization. The scattered words function like notes in a musical score, creating rhythm and repetition across the canvas. The crude figures capture the essence of the musicians rather than their literal appearance—much as jazz abstracts melody without abandoning it entirely.

Through this masterful work, Basquiat not only celebrates Black musical geniuses but demonstrates his own genius in translating the auditory experience of jazz into visual form. Horn Players remains one of the most powerful examples of Basquiat's ability to bridge cultural forms and create artwork that resonates on multiple sensory levels—including as Neo-expressionist art for Frame TV and digital gallery walls.

Hollywood Africans, 1983: Deconstructing Racist Stereotypes

Created during a trip to Los Angeles with fellow artists Toxic and Rammellzee, Hollywood Africans offers one of Basquiat's most direct commentaries on racial stereotyping in American entertainment. Against a brilliant yellow background that commands immediate attention, Basquiat painted stylized portraits of himself and his two friends, surrounded by text fragments highlighting racist Hollywood tropes.

Contract of fiction between Jean-Michel Basquiat and Helmut Diez. Image courtesy of Wikimedia Commons showing Basquiat's distinctive handwriting style, which appears prominently in works like "Hollywood Africans."

The scrawled phrases—"SUGAR CANE," "TOBACCO," "GANGSTERISM," and "WHAT IS BWANA"—reference the limited, caricatured roles historically offered to Black actors in American cinema. From plantation stereotypes to exoticized "jungle" characters, Basquiat catalogs Hollywood's racist imagination in stark text fragments, many crossed out but still clearly legible.

The title Hollywood Africans itself operates as ironic commentary, highlighting how the entertainment industry lumps diverse Black identities under reductive labels. The three contemporary Black artists in the painting—representatives of the cutting-edge hip-hop and graffiti scenes—are juxtaposed against these demeaning historical stereotypes, creating tension between authentic Black creative expression and its commercial exploitation.

Visually, the work is among Basquiat's boldest. The acidic yellow background creates an almost painful brightness that demands attention, while the figures are rendered in a deliberately cartoonish style that references the very caricatures being critiqued. Basquiat's characteristic crossed-out text operates with particular effectiveness here—acknowledging these stereotypes while simultaneously negating them.

Hollywood Africans demonstrates Basquiat's ability to combine searing social critique with formal innovation. Through vibrant color, strategic text placement, and symbolic imagery, he creates a work that deconstructs racism in popular culture while asserting the autonomy and creative power of contemporary Black artists. For more on the history Basquiat interrogates in Hollywood Africans, explore the Smithsonian’s resources on Black Hollywood. This enduring message inspires our Basquiat-style digital wall art for Frame TV.

Riding with Death, 1988: The Final Statement

Created in the final year of Basquiat's life, Riding with Death stands as one of his most haunting and prophetic images. Against a sparse, ochre background, the painting depicts a silhouetted brown figure riding atop a skeletal horse rendered in bone-white outline.

The composition is strikingly minimal compared to many of Basquiat's earlier, more cluttered works. The background is an unadorned, muddy expanse that heightens the drama of the two central figures—the rider and the death-horse. The skeletal mount has been interpreted as an allusion to the biblical "ride of the Apocalypse," while the human figure combines aspects of both strength and vulnerability.

Art historians have noted the painting's connection to Renaissance imagery, particularly Leonardo da Vinci's anatomical sketches and horse studies. This sophisticated art historical reference point blended with Basquiat's characteristic primitive style creates a haunting fusion of European artistic tradition and African-influenced imagery.

What makes Riding with Death particularly poignant is its timing. Created as Basquiat struggled with addiction and the pressures of fame, the painting seems to presage his own premature death later that year. The image of a Black figure both controlling and being carried by a skeletal horse captures the paradoxical position Basquiat himself occupied—simultaneously powerful and endangered, triumphant and doomed.

The stark simplicity of this final major work suggests an artist stripping away excess to confront essential truths about mortality, power, and racial identity. While maintaining signature elements of his style, Riding with Death achieves a classical gravity and emotional depth that signal Basquiat's evolving artistic maturity—a development tragically cut short. The work’s haunting presence is echoed in our free modern art for Samsung TV digital releases—art that blends memory and immediacy.

The Evolution of a Revolutionary Voice

When viewed chronologically, these five masterworks reveal the remarkable evolution of Basquiat's artistic vision over his brief career. From the raw energy of Untitled (Skull) to the classical restraint of Riding with Death, we witness an artist constantly refining his visual language while remaining true to his core concerns: racial identity, historical memory, the celebration of Black excellence, and the critique of systemic injustice.

What unites these diverse works is Basquiat's unmistakable visual signature—the integration of text and image, the symbolic crown, the raw expressionism, and the cultural fusion that made his paintings immediately recognizable. Each painting demonstrates his unique ability to create work that functions simultaneously as personal expression, cultural commentary, and formal innovation.

Though Basquiat created hundreds of significant works during his career, these five paintings represent pivotal moments in his artistic development and showcase the range of his creative vision. From jazz-inspired improvisations to searing social critique, from anatomical explorations to mythic imagery, they illustrate why Basquiat's work continues to resonate with viewers and influence new generations of artists.

To explore more of Basquiat’s creative journey, the Tate offers a digital archive of his key works and influences [see Tate’s Basquiat archive].

In the third and final installment of our series, we'll explore Basquiat's enduring influence on contemporary art and culture, examining how his groundbreaking approach continues to shape creative expression across multiple disciplines.

Continue to Part 3: "Beyond the Canvas: Basquiat's Enduring Influence on Art and Culture"

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Discover more Basquiat digital art downloads and Neo-expressionist art for Frame TV: Part 1: The Raw Revolution  |  Part 3: Beyond the Canvas →

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