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 05, 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 07, 2009

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 06, 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 05, 2021

bossman

Bossman is a word to tell somebody that their not wanted and nobody likes them.

Yo look at that nigga, hes a bossman

by cash#0002 February 08, 2023

bossman

A cool person who absolutely slays the day away

"omfg guys jennifer's such a bossman"

by TheOneAndOnlySubac June 12, 2022