2. Al Swearengen - Deadwood
Such a fitting name for such a sweary man; Al Swearengen is the proprietor of the bar/brothel in the pioneer town of Deadwood. Being one of the first residents to put up shop in the new settlement when it began, he immediately vied for control of its criminal activities. Gambling, prostitution and intimidation are all fair game for Swearengen (as long as he's turning a profit). Usually this would be a clear cut case of him being an unlikeable fellow but set against the backdrop of America's Wild West, he fits right in. Due to the relatively lawless nature of the time you find yourself not blaming people for taking advantage. Villains come and go throughout Deadwood's short-lived run but Al Swearengen is the constant, often becoming the lesser evil where Sheriff Seth Bullock (Timothy Olyphant) is concerned. That doesn't mean the two of them don't lock horns and when they do it's terrific to watch unfold. Ian McShane is a delight as Swearengen, bringing equal parts black comedy and menace. Hard times call for harder men, and McShane was certainly able to bring one of them to life. If there's anyone you wouldn't want to cross on this list, Al Swearengen has no doubt proven why he's absolutely a top contender.