by Fyekidd2k November 19, 2018
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
by dragonbasketball43 October 5, 2009
by The One And Only Pussymonster October 7, 2009
Something is over
by ballerstatush March 16, 2010
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.
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
Mobster: Understood.
Bossman Smooth: Here, Take my ferrari
Mobster:Thanks Bossman Smooth
by Bossman Smooth January 14, 2012
by diabeticduck April 6, 2020
by Living With Style December 5, 2021