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15.
Boss Man. Boss is an acronym spelled backwards. Sorry Son Of a B*tch. In prison the inmates call the correctional officers Boss Man. This is in no way a sign of respect but of disresepect. They are calling them a Sorry Son Of a B*tch. This is exactly why Rick Ross calls himself the Boss. He was so used to inmates calling him this term he stuck with it long after his correctional officer days.
Inmate To Guard: "Hey Boss Man"
Guard To Inmate: "I'm Rick Ross, I Am The Boss"
Inmate To Guard: "What A Dumb A**"
by PlayasNation May 26, 2009
 
16.
jerk in charge
"boss is just slang for jerk in charge" michael scott.
by moq February 01, 2009
 
17.
Adj; To be desirable in its qualities of "cooldom" and "awesomeocity".

Noun; One who "runs this bitch".
1. That midget was pretty boss when he beat up that old lady last night.

2. Boss fired Bob the other day. That, in turn, was not boss on Bob's part.
by Mylan December 18, 2006
 
18.
Final (and most likely hardest) enemy in a videogame. Bosses usually take great skill and cunning to beat.
I just beat the shit out of the boss on Metroid Prime.
by TbPlayer January 18, 2004
 
19.
adj. meaning extremely cool, awesome, or fly
That concert was sooo boss
by Grace December 23, 2004
 
20.
Boss is the name of a cult on the website vampirefreaks that is owned by two trolls on vampirefreaks by the usernames of Zig and Zag.

Matching their usernames is really actually not cool, but nobody will say anything because they're too scared.
Boss is a place for vampirefreaks members who like putting other people down. Unknowing noobs will join the cult, and be bombarded with insults that lead to them wanting to leave vampirefreaks forever.

Boss is also a place where trolling of other vampirefeaks cults.
My cult got trolled the other day, I think it came from Boss. I'll have to report it.
by NOOOOOOOOOOOOOO June 22, 2010
 
21.
A person who is of a higher life form than most feeble humans. They literally demand respect. All of their actions are aimed at consolidating their place as the top dog, and these actions are conducted in the smoothest manner possible.
Bosses often deny the fact that they are boss, but know in their hearts that they are. They are always winning.
The clothing of these men/women usually includes a classy, fitted Hugo Boss outfit.
Ari entered the room and everyone fell silent. They realised that they were in the presence of a true boss.
by theurbanfiend October 26, 2011