Played By: Ian McShane

In an era when we value subtlety and moral ambiguity in our villains, Al Swearengen is a throwback, and, most importantly, a breath of fresh air. With his lyrical dialogue and scenery chewing tendencies, Swearengen reminds us of our favorite stage villains more than he does the conflicted suburban criminals that stalk the rest of premium cable. 

At first, Swearengen was a coldly confident tyrant, but eventually, beneath the bluster and showy violence, we realize that he has more kinship with other great conflicted TV villains than first thought. Viewers grow to empathize with Swearengen as Deadwood thunders forward.

As the harsh realities and the body count of the frontier town pile up, it's easy to wonder what state Deadwood would end up in if not for a strongman like Swearengen. Mining interests, government lackeys, and internal strife threaten to tear the town of Deadwood apart at every turn. Though there is no love lost between Swearengen and Sheriff Bullock (Timothy Olyphant), by the end of the series, it becomes clear that they are both essential to Deadwood's survival.