Jean-Michel Basquiat's late works from 1987 to 1988 are a compelling and intense period in his career, marked by both creative maturity and personal turmoil. During these years, Basquiat's work continued to explore themes of race, identity, and mortality, often with a greater sense of urgency and introspection.

One of the notable aspects of Basquiat's late period is his continued use of bold imagery and text to convey complex narratives. His paintings from this time often feature a dense layering of symbols, words, and figures, creating a chaotic yet deliberate composition. For example, his 1988 painting "Riding with Death" starkly depicts a skeletal figure riding a skeletal horse, a powerful meditation on mortality and the artist's own struggles. This piece is often interpreted as a reflection of Basquiat's inner turmoil and premonition of his untimely death (SearchWorks) (Haring).

Basquiat's works during this period also show a deeper engagement with historical and cultural references. He frequently incorporated African and African-American history into his art, using his platform to critique systemic racism and celebrate Black cultural achievements. This is evident in works like "Mitsuya," a jacket he customized with his distinctive iconography, blending fashion with visual art to make a statement about identity and self-expression (Artsy).

Despite his success, Basquiat's personal life was marred by drug addiction, which significantly impacted his health and productivity. His friendship and collaboration with Andy Warhol had ended with Warhol's death in 1987, a loss that deeply affected Basquiat. The grief and isolation he felt are palpable in his later works, which often convey a sense of desperation and existential angst (SearchWorks) (Mr Feelgood).

Basquiat's final years were a period of prolific output, as he sought to assert his legacy and voice within the art world. His late works are characterized by their raw emotional power and unflinching honesty, capturing the complexity of his experiences and the broader socio-political context of the time. Despite his tragic death at the age of 27, Basquiat's art from this period continues to resonate, highlighting his profound impact on contemporary art and culture (Artsy) (Haring).