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

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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

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Cuff Da Bossman

Something is over

We won this game, cuff da bossman

by ballerstatush March 16, 2010

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Bossman Coke

Not the boss of any kind of coke, but talks about coke a lot.

Is that Bossman Coke? Yeah, don't ask him for coke though, he bought it all. Then he did all of it! There is no more coke in the entire world now, that motherfucker.

by Bossman Weed January 17, 2024

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