Jean-Michel Basquiat's self-portraits are a compelling aspect of his body of work, offering deep insights into his identity, struggles, and perceptions. Through these self-portraits, Basquiat explored themes of race, mortality, fame, and his personal experiences as a black artist navigating the predominantly white art world. His self-portraits are characterized by their raw emotional intensity, bold use of color, and incorporation of symbolic imagery.

One of the most notable self-portraits is Self-Portrait (1984), in which Basquiat presents himself with a skeletal face, a recurring motif in his work. The skeletal imagery symbolizes mortality and the fragility of life, reflecting Basquiat's contemplation of his own existence and the pressures he faced. The fragmented and chaotic composition of the painting mirrors his inner turmoil and the complexities of his identity. This self-portrait is a poignant reflection of Basquiat's vulnerability and his struggle to reconcile his public persona with his private self (MoMA).

In Self-Portrait as a Heel (1982), Basquiat portrays himself with a crowned head, asserting his identity and defiance against societal constraints. The crown, a recurring symbol in his work, represents authority, nobility, and Basquiat's self-assertion as a significant figure in the art world. The title "heel" refers to a character in professional wrestling who is the antagonist, suggesting Basquiat's perception of himself as a misunderstood and controversial figure. This self-portrait encapsulates his complex relationship with fame and his determination to be recognized on his own terms (Whitney Museum).

Basquiat's self-portraits also frequently incorporate elements of African and Afro-Caribbean culture, reflecting his heritage and the broader diasporic experience. In works like Self-Portrait with Hair (1982), Basquiat emphasizes his Afro hairstyle, celebrating his black identity and challenging Eurocentric beauty standards. This self-representation serves as a form of cultural affirmation and resistance, asserting the importance and beauty of blackness in a world that often marginalizes it. Through these self-portraits, Basquiat connects his personal identity with the collective history and resilience of the African diaspora (Tate).

Another significant self-portrait is Untitled (Self-Portrait) (1982), where Basquiat uses a combination of text, symbols, and fragmented imagery to convey his complex self-identity. The text in the painting often includes words and phrases that reflect his thoughts, feelings, and experiences, creating a layered narrative that invites viewers to delve into his psyche. The fragmented imagery and dynamic composition capture the multiplicity of his identity, highlighting the interplay between his inner world and external reality. This work exemplifies Basquiat's ability to blend visual and textual elements to create a rich, multifaceted self-portrait (Guggenheim).

Jean-Michel Basquiat's self-portraits are a powerful exploration of his identity, reflecting his experiences, struggles, and perceptions as a black artist. Through his use of bold imagery, symbolic elements, and dynamic compositions, Basquiat conveyed the complexity of his inner world and his place in the broader cultural and historical context. His self-portraits remain some of his most compelling works, offering a profound and intimate glimpse into the mind of one of the most influential artists of the 20th century (The Broad).