In 1997 Kehinde Wiley made his first trip to Africa to meet his father, a Nigerian man he had never known. This journey resonated deeply with the artist, who returned several times and established a studio practice there. Wiley documented each visit through portraiture, creating paintings of young men inspired by his African surroundings. This essay traces the impact of these experiences on the art of Kehinde Wiley, particularly his aesthetic sensibility and conceptual mindset. Wiley embraced the art of Africa as a reference, posing his subjects after traditional sculpture and postcolonial monuments while incorporating colors and patterns from textiles into elaborate backgrounds. However, Wiley’s response to Africa extends beyond formal considerations. In the spirit of Négritude he mined a collective African identity to contest former colonial hegemonies, critiquing the representation of race, status, and power in the process. Akin to the Pan-African advocates of the twentieth century, the artist employed a realist style and located a shared heritage among the African diaspora. Much like the intellectuals of Négritude who attempted to reimagine notions of “blackness,” Wiley reclaims the African subject in portraits that contest traditional, colonial, and contemporary histories. Ultimately, Kehinde Wiley’s dialogue with Africa complicates identity and representation, repositioning the African subject within the history of art to challenge the normalizing power of figuration.