Bruce Springsteen, 1978
"That is the ugliest thing I've ever seen in my life," Springsteen told Rolling Stone writer Dave Marsh when he saw this billboard. So the Boss enhanced it with graffiti: Springsteen, saxophonist Clarence Clemons, bassist Garry Tallent, and some crew members arrived late at night with twenty cans of black spray paint. Springsteen wrote "E Street" himself while standing on Clemons' shoulders. "I wanted to get to my face, and paint on a mustache," he said. "But it was just too damn high."