The artist who painted Tishcohan and Lapowinsa was born in Sweden: Gustavus Hesslius, the first portrait artist of the Pennsylvania colony. Painting a Lenape man’s face would have been of a piece with his broader conception of himself as simply a painter. This chapter involves a cultural encounter between European portrait practice, European and Lenape forms of negotiation, and Lenape face-and body-painting practice. “Identity” here oscillates between how a culture identifies and categorizes an individual subject (expressed through the material and generic regimes of art), and the qualities of that subject experienced within and in contact with others, as a physical, psychological being. As the most populous and wealthiest city of the American colonial era, Philadelphia produced a significant amount of 18th-century art. On the walls of the colonial gallery at the Philadelphia Museum of Art hang long rows of portraits of European settler colonists: women and men, children and pets.