Cleopatra VII, the ruler of Ptolemaic Egypt whom everyone remembers.
Normally I would not depict a Ptolemaic ruler as black, since the dynasty had Macedonian origins, but anthropologists studying the remains of Cleopatra's half-sister Arsinoe reported that she had both African and European physical characteristics which suggests that she and perhaps by extension Cleopatra herself may have been biracial
. In other words, Cleo could have looked more like Rihanna or Beyonce than Angelina Jolie or Elizabeth Taylor. However, for this drawing I used one of my online friends
as a reference for Cleo's expression and facial features.EDIT:
Now with shading and highlights!