Frank Ocean, Blonde
For this piece, the main challenge was that the original photo's lighting is pretty consistent throughout his face. This made creating the shadows and highlights a little dramatic to get the right look.
Kanye West, The Life of Pablo
This piece had the opposite problem as the first one, as the original lighting is quite exaggerated. This made the goal to tone down the shadows and highlights to make it more realistic.
Chance The Rapper, Coloring Book
For the final illustration, the main challenge was creating the hat because the other two didn't have another element like this one. I used a gradient on the sticker, dashed strokes for the stitching, and a very subtle drop shadow on the "3" to create the effect of it being embroidered and look 3D.
Created using: Adobe Illustrator