Bruce Springsteen got “The Boss” nickname long before he ever became a big recording superstar in his club days when he was tasked with collecting the band’s pay from club owners and distributing it amongst the band afterwards. Springsteen never cared too much for “The Boss” because of his distaste for bosses. According to others it derives from his ability at Monopoly board game.
On December 6, 2009 at the White House, during a ceremony to deliver awards to artists who have distinguished themselves in the spread of American culture, Barack Obama introduced Springsteen using his well-known nickname:
« I’m the president, but he’s the Boss.”