Tim O’Brien was commissioned by XXL magazine to paint Tupac Shakur as he would look if he were alive today, to mark the 15-year anniversary of the rap legend’s death. 

Tim’s sketch imagines some added weight in Tupac’s face and cheeks, skin less smooth, pores are more evident.  And, of course, grey hairs start to come out. “I think Tupac would have had some evident eye wrinkles based on how he looked then,” says Tim.  

“I was kind to the late Tupac and imagine he lived a decent life, not eating himself into oblivion and basically keeping his famed look.  There is the slightest hint of anxiety I added to his face which I felt made him look less posed, less comfortable with being seen.”

Tim’s painting from 15 years ago of Tupac at the time of his death provided vital source material for this new portrait, as did the artist’s own experience of maturing.