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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!
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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.
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A term to used to describe Kerry Trapps, Stranger Pings Team Leader.
A kebab shop worker or owner who takes their job seriously.
"Can I have mayo on my kebab please bossman"
Bossman is a word to tell somebody that their not wanted and nobody likes them.
Yo look at that nigga, hes a bossman
A cool person who absolutely slays the day away
"omfg guys jennifer's such a bossman"