Art by Shepard Fairey

Fairey's career started small in 1989 with a sticker of wrestler André the Giant's face captioned "Andre the Giant Has a Posse," a skate-culture joke that slowly evolved into the globally recognized OBEY brand and visual style. His most consequential single image is the 2008 Obama "HOPE" poster, which he distributed for free by the hundreds of thousands during the campaign; the photograph he'd based it on triggered an Associated Press copyright lawsuit that ended in settlement, and separately, Fairey was convicted in 2012 of destroying and fabricating evidence during that case. He's been arrested multiple times over the years for unauthorized street work, including once at the opening of his own solo museum show.