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 kebab shop worker or owner who takes their job seriously.

"Can I have mayo on my kebab please bossman"

by Living With Style December 5, 2021

Bossman

Saywan Tahir also referred to as S2

Saywan is the ultimate Bossman

by S1 October 19, 2021

Bossman

Will Smith.

Bossman keep your head up King

by willsmithsuppoter July 19, 2020

Bossman Smooth

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

by Bossman Smooth January 19, 2012

Bossman Flop

This particular belly flop encompasses the traditional belly flop with the addition of stomach slapping, gestures and verbalized bravado proclaiming himself to be a profound belly flopper and often challenging other belly floppers to a belly flop dual.

My Bossman Flop was off the hook! it was the mother of all belly flops! I challenge anyone to out belly flop me! The above statements are normally made at the sametime as strutting around like a rooster and slapping one's belly with their hands.

by Jamesamw June 6, 2017