Springsteen or Steinbrenner?
Jos the Boss was the first name to come into my head.
Alyssa Milano?
Big Jim Walker was “Boss”, just because. Rumor has it he was also a pool shooting son of a gun. Unfortunately, he fan afoul of a South Alabama country boy, known as Willie McCoy. Didn’t end well for Big Jim.
Judith Light, of course.
Bruce, obviously. He was appointed by Sinatra (The Chairman of the Board).
Tony Danza.
Bruce is The Boss everywhere. George was The Boss only in Yankee Stadium, or at the most in baseball.
Elton John.
So many bosses, so few parameters.
Clarence Clemmons says it’s Bruce. But that’s just because Bruce kissed him in the mouth. 
I guess I have to go with Danny Pintauro.
Springsteen sucks so it must be Steinbrenner…
Again, I’m having a problem finding a common measure by which to compare these very different people.
Both were called The Boss.
So am I, sometimes. Without the “The”.
I love music, but I’m filled with ennui towards professional baseball.
Not a fan of either, really, but if pressed I would say Bruce.