The painting by Kehinde Wiley is called Judith and Holofernes, which refers to a story from the apocryphal Book of Judith which inspired a whole bunch of art during the Renaissance and Baroque periods. While the original story did involve a woman whacking off a guys head, Wileys choice to use a black woman holding a dead white woman's severed head is clearly a deliberate one. Wileys become pretty famous for his reimagining of traditional European portraits using black people as stand-ins.
The story revolves around Judith, a daring and beautiful widow, who is upset with her Jewish countrymen for not trusting God to deliver them from their foreign conquerors. She goes with her loyal maid to the camp of the enemy general, Holofernes, with whom she slowly ingratiates herself, promising him information on the Israelites. Gaining his trust, she is allowed access to his tent one night as he lies in a drunken stupor. She decapitates him, then takes his head back to her fearful countrymen. The Assyrians, having lost their leader, disperse, and Israel is saved. Though she is courted by many, Judith remains unmarried for the rest of her life.
1613 - Judith with the Head of Holofernes by Cristafano Allori
I’m referring to the new “portraits” of the Obamas that this artist did, not the one with the beheaded woman by the same artist.