The Boss

Could there be any musician more firmly rooted in blue-collar, working-class values than Bruce Springsteen? More likely to speak on behalf of the downtrodden, more likely to sing on the side of labor? (Okay, the answer is yes, but you get my point.) So isn't it funny that he is called "The Boss"? Sure it is, but why does no one but me find that odd?

(According to Wikipedia, it's because when the E Street Band was nascent, he was the one who arranged gigs and collected and distributed earnings. I wonder, was it even than an intentional irony, or did it just turn into one later?)