In a video game called "Vampire: The Masquerade - Bloodlines", a character called "Gorgeous Gary Golden", always refers to the player as "boss". Here are some examples from that first dialogue:
"We're having a wrap up party for The Misfits about forty years late. Cast and crew only, boss."
"How do you know I'm even here, boss?"
"I'm over here, boss! Wait, maybe I'm over here! Or maybe I'm behind you, with a hatchet in my hand..."
"I don't know, boss. You tell me. After all, I didn't crash your party."
"You don't say. Wake up, boss! Who do you think you're dealing with?"
"Because I like the sound of my own voice... It's not everyday we get visitors, boss!"
Not living in a country where English is the native language, this sounded odd to me. The player is just meeting him for the first time, and he doesn't have any relationship with Gary that would justify him being treated as a boss. It's also not a compliment either, since Gary doesn't really care for him.
I'm guessing it's just his way of talking with people. Maybe this expression is popular somewhere, or maybe it's a throwback to an expression that was popular before. I also checked some online dictionaries, but they don't mention anything about this usage of the word boss.
My question is this: Is this an expression related with a certain place and/or time, or do you think this is a only a random quirk of this character and so isn't a reflection of anything historical?