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

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

Cuff Da Bossman

Something is over

We won this game, cuff da bossman

by ballerstatush March 15, 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

you'll know a true bossman when you see him.

*points* "that guy is a bossman"

by chodemane August 19, 2022

Bossman

Any bloke that runs a corner shop North of brum and is usually of Pakistani heritage

“…Bossman will sell me 3 packs of Manchester’s for a tenner…”

by Stereotyper666 May 3, 2025