John Wayne, "True Grit"
He’s an aging, one-eyed, overweight, trigger-happy slob who never seems to miss a drink of whiskey, which means he’ll shoot you as soon as look at you…and even without proper depth perception, you can be damned sure he won’t miss. Rooster Cogburn’s been a Marshall for six years, and in that time, he’s killed 24 people, which he chalks up to the fact that “it’s a dangerous business.” Mind you, he was probably drunk for half those kills, but even without the courage of alcohol flowing through his veins, there’s little doubt that Cogburn’s a man of…wait for it…true grit.
Definitive badass moment:
When Rooster finally meets up with Ned Pepper, Mexican Bob, and the Parmalee brothers and utters his immortal line, “Fill your hand, you son of a bitch!”
Classic badass line: “Young fella, if you're looking for trouble, I'll accommodate you.”
Occupation: US Marshall
Strengths: A quick draw that has no problem shooting to kill
Weaknesses: Overweight, only has one eye, and enjoys a stiff drink a little too often
Ian McShane, "Deadwood"
As the owner and proprietor of the Gem saloon and brothel, Al Swearengen deals in booze, whores and corruption, and while he’d prefer to let his goons handle the dirty work, Al has no problem slitting your throat himself and then feeding you to the pigs in Chinatown if you pose a problem. His goal is simple: to make a fortune off the poor schlubs in Deadwood who spend their days prospecting for gold in the neighboring hills. He’ll share a bottle of whiskey with you, but only if you have something he wants, and if you do have something he wants, Al will figure out a way to get it from you. Calculating and cold-blooded, he’s as quick with an insult (“Get a fucking haircut. Looks like your mother fucked a monkey.”) as he is with a blade. And if you’re one of those crooked Yankton cocksuckers, it’s best if you just avoid the Gem altogether.
Definitive badass moment: Passing several kidney stones without any help or medication. Unimpressed? Have you ever done it?
Classic badass line: “Pain or damage don't end the world. Or despair or fucking beatings. The world ends when you're dead. Until then, you got more punishment in store. Stand it like a man...and give some back.”
Occupation: Owner of the Gem Saloon, entrepeneur
Strengths: Fierce and determined to get exactly what he wants no matter the cost, with the help of his unfailingly loyal crew
Weaknesses: That willingness to do whatever it takes to get what he wants has, on more than one occasion, cost Al dearly