A short lived cartoon series on the internet, based on a security guard from North Quincy high school in Massachusetts, where it also has had a cult following.
Name used as a sneaky, low-life way of letting someone know you are better than them, or that you really just dont give a shit what their name is, whether you know it or not. Other nameledouche for "bossman" are hoss, cheif, ace, slick, boss, broskie etc. Often these terms are used by "bros," douchebags, and guidos.
Dude: "bartender can i have two beers please"
Guido: "yea, here you go bossman"
Dude: "Fuck you douchebag"
Guido: "Sorry chief, is there a problem?"
Dude: "yea there's a problem, you know my name cause you just checked my ID, and it's not bossman or cheif! asshole!"
Guido: "oh my bad hoss"
Dude: "dammit you really are a moron"