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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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The smoothest criminal ever.
They typically lead an organization of mobsters and have lots of gun's,cash, and dope.
They're a very fair boss to work for.
Bossman Smooth: Make sure Joey isn't seen again.
Mobster: Understood.
Bossman Smooth: Here, Take my ferrari
Mobster:Thanks Bossman Smooth
Rapper out of Port Salermo, Florida. known for "Get in with Me", "Mr. Pot Scraper", and "Finesse" among many other fire tracks.
Bossman Dlow is perhaps the greatest rapper to pop off in 2024, and the best is yet to come for him. He is soon to drop some of the greatest albums of all time and end up in the Rock & Roll Hall of Fame, on the Hollywood Walk of Fame, you name it.
Have you heard the new Bossman Dlow project, "Mr. Beat the Road"?
Hell yeah, it's fire. Forget all that other garbage music. Best album to date.
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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"