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The Boss of Old Sydney Town 

Old Sydney Town was a tourist attraction on the Central Coast depicting early settlement life in Sydney. This colonial attraction was a great success throughout the 80’s. So popular, local residents would dress in period costume contributing to the atmosphere of role play. One such character, was a young boy from Umina named David who was commonly known as the Boss of Old Sydney Town.
The Boss of Old Sydney Town was a bright young boy from Umina

pay the cost to be the boss 

pay the cost to be the boss — These are watch words for people IN THE STRUGGLE. No success comes without SWEAT EQUITY and with that work comes the privilege of OWNING THE HEAD OF THE TABLE.

These words were featured in songs by both B.B. King and James Brown as explanations both of the work it takes to be at THE TOP OF YOUR GAME and the privileges afforded to one in that position.

Swagger comes as a result of THE GRIND.
1) Nobody gives you NOTHING; you gotta pay the cost to be the boss!!!!

2) Lyrics Sung by B.B. King:

“ You gotta be crazy, baby
Just gotta be out of your mind
As long as I’m payin’ the bill

I’m payin’ the cost to be the boss…”

3) Lyrics sung by James Brown:

“Paid the cost to be the boss
Paid the cost to be the boss
I’ve Paid the cost to be the boss

Look at me

know what you see
See a bad mother
Look at me

Know what you see
See a bad mother

Paid the cost to be the boss
Paid the cost to be the boss

Look at me

Know what you see
See a bad mother

Huh…”

I'M the boss 

What a 4 year old said to his Dad, after hearing that phrase from him many times.
The little kid was asserting himself when he said 'I'll show You who's the boss around here; I'M the boss, loudly.
I'M the boss by Starchylde May 25, 2016

talk to the boss 

do me a fovour and I'll do you one
wife: "i saw a lovely dress that would be just right for Fiona's wedding"
husband (unzipping trousers): "you'll need to talk to the boss honey !"
talk to the boss by the-boss October 28, 2006

Fighting the Boss 

The association of a particularly bad hangover or come down with the end of level, hard to beat boss characters in a video game.
You: how are you feeling after last night mate, I'm fucked?
Me: yeah same here mate, I've been fighting the boss all day
Fighting the Boss by Blue Stuff August 7, 2011

Walter "Maynard" "The Boss" Ferguson 

The greatest high note trumpet player to have ever lived.
Point. Blank.
R.I.P.
"Have you ever heard of Walter "Maynard" "The Boss" Ferguson?"
"Nah, who's he?"
"Only the greatest high note trumpet play to have ever lived. I mean sure others can play as high as him and higher, but there'll never be another Maynard Ferguson (R.I.P.); listen to his rendition of MacArthur Park and you'll see what I mean."
"Alright thanks man, I'll definitely make sure I check him out."