Barack Obama by Shepard Fairey
Date: December 29, 2008
By now, we've all seen Shepard Fairey's famous Barack Obama Hope poster. Dude even got himself a shout-out from Jay-Z on Magna Carta Holy Grail. The success of the Hope poster got him the opportunity to do another portrait of Obama for the cover of TIME, joining the ranks of Andy Warhol, Al Hirschfield, Stanley Glaubach, and others.