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Bossman Bailey

this refers to the name that Matt Bailey received in early September of 2009. He goes by Bossman Bailey when he defeats less competent people in bowling by one pin, even though it was only the fourth time the Bossman had played in his life. The Bossman Bailey rules over The Boss and all other Boss-like references

Mason: your a bitch!!!

Bailey: you can call me Bossman Bailey!

by dragonbasketball43 October 5, 2009

3๐Ÿ‘ 3๐Ÿ‘Ž


Bossman Bailey

A bitch that narrowly beats out a superior player in a game of bowling.

Cody: I cannot believe he just beat you, and by one point!

Carson: I know, he's Bossman Bailey.

by The One And Only Pussymonster October 7, 2009

1๐Ÿ‘ 3๐Ÿ‘Ž


Cuff Da Bossman

Something is over

We won this game, cuff da bossman

by ballerstatush March 16, 2010


Bossman

A term to used to describe Kerry Trapps, Stranger Pings Team Leader.

our kez is a BOSSMAN

by diabeticduck April 6, 2020


bossman

A kebab shop worker or owner who takes their job seriously.

"Can I have mayo on my kebab please bossman"

by Living With Style December 5, 2021


bossman

A cool person who absolutely slays the day away

"omfg guys jennifer's such a bossman"

by TheOneAndOnlySubac June 12, 2022


Bossman

Acts like the defender of all that is "bruv". Can easily be identified by the following characteristics:
- Wears caps backwards
- Always in hoodie and jeans
- Using bossman signs like backwards peace hand gestures

"Is that bossman over there?"
"Yeah, it's my guy big man number 1 smurf big up since day 1 my g the bossman innit"

by BabajeeCorp February 7, 2021