Henry Taylor's series focusing on political and cultural icons showcases his deep engagement with historical and contemporary figures who have significantly impacted society. His portraits capture the essence of these individuals, portraying them with a unique blend of realism and symbolic depth that speaks to their personal and political significance.

One of Taylor's most recognized works in this series is "Cicely and Miles Visit the Obamas" (2017), a visionary portrait that time-shifts Cicely Tyson and Miles Davis into a setting with Barack and Michelle Obama at the White House. This painting juxtaposes two powerful couples from different eras, highlighting their influence on American culture and history. By placing Tyson and Davis in the contemporary context of the Obamas' presidency, Taylor creates a dialogue between the past and present, celebrating Black excellence across generations (Culture Type) (Culture Type).

Taylor's work often features other significant figures such as Eldridge Cleaver, a prominent member of the Black Panther Party. In his portrayal of Cleaver, Taylor delves into the complexities of Cleaver's legacy, balancing his role as a political activist with his controversial later years. This nuanced depiction reflects Taylor's broader approach to his subjects, acknowledging their multifaceted contributions and the broader social context in which they operated (Culture Type).

Another notable painting is "The Floaters" (2017), which was adapted into a large-scale mural displayed on the High Line in New York City. This work, initially featured in an exhibition at Blum & Poe gallery, presents a serene pool scene that contrasts with the more intense subjects of Taylor's other political and cultural portraits. Despite its peaceful imagery, "The Floaters" still engages with themes of leisure and respite within the Black experience, subtly commenting on the intersections of race, relaxation, and visibility in public spaces (Artsy) (Culture Type).

Taylor's series is not just about honoring these figures but also about placing their lives and achievements within the broader narrative of Black history and culture. His works serve as both tributes and critical examinations, offering viewers a chance to reflect on the ongoing struggles and triumphs of Black individuals in America. By doing so, Taylor's art fosters a deeper understanding of these icons' impacts and the enduring relevance of their legacies (Artsy) (Culture Type) (Culture Type).