used a sperm motif as symbolic of masculinity and gender. This reimagining was also seen in Wiley's VH1 commissioned piece, where he was asked to paint honorees for the 2005 Hip Hop Honours program. Wiley depicted the rapper Ice T as Napoleon and Grandmaster Flash and the Furious Five as a Dutch Civic guard company from the 17th century. Sometimes Wiley changes the gender of figures portrayed in the older works. In Portrait of a Couple from 2012, he replaces the couple (man and woman) depicted in the original painting from 1610 with a pair of young men. The same year, he exhibited two variations on the Judith Beheading Holofernes Biblical story famously painted by Caravaggio,replacing the male Holofernes with female figures. New York magazine described one of these as depicting "a tall, elegant black woman in a long blue dress. In one hand, she holds a knife. In the other, a cleanly severed brunette female head". Wiley said about this work: "It's sort of a play on the 'kill whitey' thing". A second painting entitled Judith Beheading Holofernes also features a modern-day black woman as Judith and a white woman as Holofernes, challenging the viewer's expectations of this familiar motif, inviting political readings, and "bending a violent image from art history—which is rife with them [...]—to the needs of a country that is reexamining the violent underpinnings of even its most benign-seeming traditions." Art critic Walter Robinson remarks that this reimagining of the Judith/Holofernes story "suggests, with a jovial brutality, that Judith would prefer to be done with white standards of beauty." Masculinity and femininity Much of Wiley's work focuses on male figures. This is an intentional choice by Wiley to reflect on the lack of female figures in art history in portraits due to societal norms. The way in which Wiley positions his figures and how he paints them switches the feminine and masculine roles. He emphasizes features of his Black figures that eroticizes them in a way women were traditionally portrayed. He focuses on their bodies, includes motifs like sperm that reference their vitality, and poses them in vulnerable positions. The floral and decorative backgrounds put into question the idea of masculinity. The patterns of lace and flowers are often associated with femininity and by submerging his male figures in these ornate backgrounds, Wiley acknowledges the beauty and youth of his subjects. Power Wiley's intent when he