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 cool person who absolutely slays the day away

"omfg guys jennifer's such a bossman"

by TheOneAndOnlySubac June 12, 2022

bossman kay

Richest Rapper in The World Goes By Yung Kay

Bossman kay has more money than the factory make.

by Gillboy dead April 18, 2018

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