Rick Ross (rapper who frequently says, "I'm the boss")
Tony Danza (Had own TV show called, "Who's The Boss")
Bruce Springsteen (nicknamed "The Boss")
George Steinbrenner (nicknamed "The Boss")
Larry David playing George Steinbrenner on "Seinfeld" (played a person who was nicknamed "The Boss")
Andy Samberg (played a boss who acted "like a boss")