What's the origin and popularity of the word "boss" in the context of referring to the person you're talking with?

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?

ODO gives a definition

a person in control of a group or situation

which fits the context you give.

There's not much by way of history in ODO though.

OED has

a. An orig. American equivalent of ‘master’ in the sense of employer of labour; applied also to a business manager, or any one who has a right to give orders. In England at first only in workmen's slang, or humorously, = ‘leading man, swell, top-sawyer’; now in general use in Britain.

b. In American politics, a manager or dictator of a party organization.

Use (a) is attested from around 1650.

It strikes me that the usage you quote is a caricature of 1930's New York, where [in such caricatures] gangland bosses are invariably referred to as Boss, and the word is used either in deference or mock deference to others as well. But I'm not sure I could come up with any documentation as to whether that was actually the case or not.

The tone of the quoted dialog suggests interpreting Gorgeous Gary Golden's use of boss as mocking and sardonic. GG takes the “Yes, Boss” submissive-slaves racial stereotype found in many movies of the 1940's (with black field hands or laborers and a white overseer) and ironically plays against it.

The recordings that Alan Lomax made of the work chants of black prison farm workers at Angola State Prison in Louisiana in the late 1930s and then again in 1947–1948 include snippets with one of the group leaders among the prisoners. This man twice in a 2 minute, 11 second interview snippet addresses the white interviewer as "Boss," though the interviewer clearly does not have any sort of institutional authority over him. You can hear the snippet on YouTube at http://www.youtube.com/watch?v=mkxhb9Y3vOg.

This prisoner's use of boss may be habitual from addressing white overseers at the prison, but I think it's very possible that boss served as an all-purpose term of respect by Southern black men toward Southern white men during the era when lynching was an ever-present danger for offenses as slight as perceived disrespect.

The use of boss throughout the United States as a playful form of respectful address may have crossed over from that usage or it may have occurred much earlier.

J.S. Farmer & W.E. Henley, Slang and Its Analogues (1890) has an interesting entry for boss:

Boss, subs. [American and English].—1. A master; a head man; one who directs. [From the Dutch baas, a master.] Few words have acquired a greater hold on American life than this term, and the primitive meaning of master, overseer, or superior of any kind, though in a large measure retained to this day, has been widened out in every direction. The political BOSS is the leader whose word is law to his henchman. Boss Tweed, of New York, is believed to have been the first to bear the title in a semi-official way. The phrase BOSS RULE is said to have been invented by Mr. Wayne MacVeagh, and employed by him in speeches in Chicago. It is now in common use in this sense. In the first two quotations [one from 1590 and one from 1679] the word appears to be used much as in the modern sense.

The 1590 quotation cited by this book is from Christopher Marlowe's Tamburlaine the Great, and arises in a dispute between Turkish Queen Zabina and Egyptian Princess Zenocrate:

Zabina: Base concubine, must thou be plac'd by me

That am the empress of the mighty Turk?

Zenocrate: Disdainful Turkess, and unreverend boss,

Call'st thou me concubine, that am betroth'd

Unto the great and mighty Tamburlaine?