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1.
This is considered a mix of both formal and casual. You say this to someone when you respect them in the sense that you acknowledge they're in charge of the situation.

It can also be defined to the equivalent of the phrase, "Cool guy".
What's crackin, boss man?

Sure, whatever you say boss man.

What can I do for you today, boss man?
by Jack Mehoff XXI October 31, 2009
 
2.
A term used to describe a man, usually a superior or partner in the workforce, who commands great respect by his actions and presence, with no need for threats or cheep tricks. Depending on the person, could also be considered a badass
"Hey, who's the guy in the coat?"

"He's the Bossman, and I wouldn't get on his badside. I heard he once took on an entire street gang with only a car, his older brother, and a hammer, and manged to get away with only a totaled window."

"Wow, he's a badass!"
by Timothy C. Ouellette December 22, 2008
 
3.
nickname referring to Giants tight end Kevin Boss
1.Bossman scored a touchdown for my fantasy team today.

2. Bossman doesn't like it when people feed him stale potatoes, cause thats kind of a dick move.
by Revismaster February 02, 2010
 
4.
Someone who shows complete authority around any living thing.
Don't fall asleep in class Max. Sorry but no one tells bossman what to do.
by WinstonM September 16, 2013
 
5.
A border-hopper with a dirty sanchez who thinks he's good at pong, and thinks he's hot shit..Bossmen tend to fish often, be very fond of the Mexican race, and be huge drama queens.
"That tool at the pong table was such a bossman"
by Iceman0212 April 11, 2009
 
6.
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.
"Hey, guys, No smoking on school grounds, guys. K guys?"- Bossman
by Jfir May 28, 2008
 
7.
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"
by NismoG April 02, 2009