Let me say first that you should all be extremely proud of me for making it this far before indulging myself with my favourite villain of all time, Al Swearengen. Come to think of it, Al isn’t just my favourite villain, he’s my favourite TV character of all time, period. So the fact that I made it through five Villains of the Month before scratching that itch shows remarkable restraint, don’t you think? Yes, thank you, I think so too.

If you’re not familiar with Al Swearengen, saloon/whorehouse owner and honorary King of Deadwood, then you haven’t seen HBO’s celebrated Shakespearean western – in which case, you should stop what you’re doing right now and binge watch it. Because it so happens that you’ve missed out on the network’s most brilliant show – which, considering the consistent quality of HBO programming, pretty much makes Deadwood the most brilliant show ever made. Yes, you read that right: I said Best. Show. Ever. Go ahead, try to argue with me. I WILL TAKE YOU ALL.

Ahem. Where were we?

Ah, yes. Al. Now before we get started, let me anticipate a possible objection. Some might be tempted to argue that Al doesn’t really qualify as a villain, since he occasionally allies himself with the show’s heroes, including Sheriff Seth Bullock, Deputy Charlie Utter, and eventually even the Widow Garret, whose feckless husband Al had tossed off a cliff in the early episodes of Season 1. Fair point. But I’d argue that even though Al often works alongside the good guys, it would be a mistake to consider him one of them. After all, we’re talking about the sort of man who’s willing to murder an orphaned child to cover up his crimes. And if by Season 3 he’s drifted into antihero territory, it’s not because he’s gone soft. Joining forces with Sherriff Bullock isn’t a matter of shared values, but of expediency. It’s like the Joker teaming up with Batman – and actually, that’s not a bad analogy, because like Batman, Seth Bullock is a pretty dark hero in his own right.

Villain or antihero, Swearengen isn’t all that impressive on paper. He’s a pimp, a murderer, and “when chance affords” a thief, but he’s not particularly artful at any of these. He operates a low-end whorehouse, runs a pretty transparent con, and solves most of his problems in the same crude fashion: by cutting throats, often in his own office. (A running joke has Al on hands and knees with a horsehair brush and a bucket of soapy water, congratulating himself on how well he scrubs a bloodstain.) Any serious law enforcement would have seen him at the end of a rope years ago, and even a modest challenge to his power, like that posed by rival saloon owner Cy Tolliver, stitches him up for episodes at a time. He can barely hold his own in a fair fight, so he avoids them wherever possible, relying on his henchmen to do most of the dirty work. Not exactly the stuff of greatness.

The thing is, Swearengen doesn’t aspire to greatness, not in any real sense. He thinks of himself as a survivor, and from the glimpses of backstory we’re given, it’s tough to argue. The phrase troubled childhood doesn’t quite cover it. Raised in an orphanage after his prostitute mother abandoned him, Swearengen’s ambitions don’t stretch much beyond clawing his way to the top of the shit pile he grew up on. That means running a successful business in a successful town, ideally one with just enough law and order to keep things running smoothly without really getting in his way. Pretty humble ambitions, and even then, he’s acutely aware that he’ll lose it all one day, most likely in bloody fashion. If Al meets his maker old and warm and well-fed, he’ll consider that a win.

That’s not to say he won’t grab what we can, when he can, and do whatever it takes to hang on to it. Al rarely hesitates to do what’s “necessary”, even when he’d rather not – and that’s what sets him apart from the rest of the characters. Deadwood’s other villains, and even its heroes, tend to commit their darkest deeds in the heat of the moment. Not Al. When Swearengen does something awful, it’s almost never on impulse; it’s deliberate, carefully weighed, and as passionless as it is remorseless. On the rare occasions when his emotions do get the better of him, they’re more likely to inspire a spontaneous act of mercy than one of violence, like the time he hesitates with his knife at Bullock’s throat, unable to do the deed because a “cow-eyed kid” is looking on.

So in theory, what we have here is a pretty bog-standard criminal with no special talents and no lofty ambitions, who surrounds himself with a group of fairly unremarkable henchmen and who isn’t, when push comes to shove, especially evil.

Now that I’ve spent the better part of a page laying out all the ways Al Swearengen shouldn’t qualify as a great villain, allow me to explain why he’s the Best Ever.

Put simply, it’s because he’s one of the most compelling characters ever to grace the small screen.

Look at those eyes, will ya?

To begin with, creator David Milch and his co-writers struck a delicate balance in keeping Al’s behaviour logically consistent without being predictable. There’s an imperfect, very human sort of coherence to him, such that even when he’s doing something unexpected, it’s in keeping with his character. Take, for example, his strong protective streak, which manifests itself in all sorts of interesting ways. Part of it is probably down to power: Al has it, and he enjoys wielding it, as anyone who was himself once under the boot tends to. But I think it’s more complicated than that.

As his backstory attests, Al attended the School of Hard Knocks. That made him resilient and ruthless, but it also creates a bond with his fellow SHK alumni. Seen through that lens, behaviour that at first seems puzzling starts to make sense. His rescuing of Jewel, for example, though her disability makes her unemployable as a whore. Or his insistence that Trixie keep learning accounting, even though her betterment means he risks losing her forever. Or his pep talk to the recently-assaulted newspaperman A.W. Merrick, which gives us one of the most celebrated scenes in the series. Even his mercy killing of an ailing priest owes to this hard-bitten worldview:

“You just gotta kill it and put an end to it. You don’t linger on about it. You don’t go around fucking weeping about it. … You gotta behave like a grown fucking man. … Don’t be sorry. Don’t look fucking back. Because, believe me, no one gives a fuck.”

This, too, is a pep talk – but for himself, steeling himself for what he knows needs to be done. The killing itself is both chilling and tender, with Al mechanically explaining to an underling how to smother a man (“like packing a snowball”) before whispering in the dying man’s ear, “You can go now, brother.” He emerges from the room visibly shaken, but when he realises Trixie is watching, he straightens and fixes her with a steely look, unwilling to show weakness.

His relationships are fascinating too. While most of Deadwood’s characters relate to each other in fairly straightforward ways, their dealings with Al are invariably complex and revealing. Take Seth Bullock. He quickly establishes himself as the biggest pain in Al’s balls – and precisely because of this, Al concludes that Bullock needs to be made sheriff. This will prove endlessly inconvenient, putting “his holiness” directly in Al’s path from time to time, but Swearengen is prepared to sacrifice short-term convenience for long-term gain, which he reckons Bullock will provide by lending legitimacy to the town, thus helping safeguard everything Swearengen has built. Nemesis and ally both, Bullock is also in a very real way Swearengen’s tool – or better yet, a weapon, one Al knows could blow up in his face at any time.

Or how about Alma Garret, whose husband Al murdered, and whose ward he ordered dead? He also tried to cheat her out of a massive gold claim, but now he’s thought of an even better use for it: as surety to establish Deadwood’s first bank, yet another cornerstone of the town he’s working so diligently to establish. Thus, by Season 3, we have Al vaulting (somewhat implausibly) over the balcony to protect Alma from a hail of bullets. Not because he’s a good guy, but because keeping her alive means keeping her bank open, which serves his interests. As for Alma, she has little choice but to accept his protection, and they end up with a mutual, grudging sort of respect.

There’s Trixie, his best friend, confidante, and sometime lover, whom he beats and very nearly kills. Dan, the cold-blooded killer who blubbers like a child when Al seems to favour another henchman. Johnny – sweet, dumb Johnny – who screws up left and right, but whose incompetence Al refuses to punish in any meaningful way.

Swearengen abuses each and every one of his people – physically, emotionally, and in Trixie’s case, sexually – and yet they love him. It’s twisted, fucked up, deeply unhealthy love – but that doesn’t make it any less powerful. So much so that when Doc Cochran delivers him from the brink of death, their reaction gives us this extraordinary scene:

And it’s not just his henchmen who succumb to Al’s undeniable charisma. He’s the unofficial mayor of Deadwood, the man to whom all turn in a crisis. It’s Al who chairs the meetings of the town’s notables, whether it’s to organise the response to an outbreak of smallpox or the town’s first elections.

I’ve often wondered whether Milch and co. always intended for the character to be the centre of gravity for the show, or if Ian McShane’s magnetic performance just dragged them into his orbit. (Probably a bit of both. The show was intentionally Shakespearean, but it’s hard to imagine another actor pulling off soliloquies while being serviced by his whores.) Regardless, the result is an incredibly textured character, who is by turns chilling, sympathetic, and hilarious – sometimes all at once.

Trixie sums it up best:

“There’s entries on both sides of the fucking ledger, is the fucking point.”

All this is in perfect keeping with the show’s gritty brand of realism. From the earliest episodes, Deadwood establishes itself as a place where bad people can do good things, and progress toward modernity is less a march than a bare-knuckled brawl. If the Bible shows salvation being delivered in a barn, Deadwood gives us civilization birthed in horseshit, mud, and moral quagmire. Which sounds about right to me.

OK, wow. I’ve let this one get away from me, haven’t I? And I could go on, believe me. So before I go entirely off the deep end, let’s get to The Machine.

Strengths: A remarkably strategic thinker, anticipating trends, reading human behaviour, and predicting how all of it will affect his interests – before formulating an appropriate counter-move. Has a keen eye for talent and knows how to use it to his advantage.

Weaknesses: A hair-trigger temper, an abundance of pride, and a deep-seated fear of showing weakness – the combination of which sometimes backs him into a corner, committing him to a fight he doesn’t really want. On the other hand, given to occasional flashes of sentimentality that undermine his long-term interests – including when it comes to choosing henchmen, some of whom are downright liabilities (I’m looking at you, Johnny).

Best Quote: Dear God, this is like choosing one of your children. If I have to pick a single sentence, it’s this: “You can’t cut the throat of every cocksucker whose character it would improve.” Words to live by.

Villain Points:

Lair: The Gem Saloon. What it lacks in elegance it makes up for in character(s). Inside, it’s a veritable petri dish of scumbags; outside, Al watches the world unfold from his balcony, sipping his coffee and surveying his domain like the Pope. Plus, it’s not every lair where a guy can get “12-pointed” (that is, impaled upon the antlers of a deer). 5 points.

Toys: A gun, a knife, and the severed head of a Sioux warrior. 3 points – for the severed head.

Henchmen: Stalwart Dan and clever Silas are easily worth 2 points apiece, and Trixie is worth another (her second point going to Team Bullock). Then there’s dim-witted Johnny. -3 points for him. Way to let the team down, bro. 3 points.

Intimidation factor: People literally shit themselves in Al’s presence. The only two people who aren’t afraid of him are Seth Bullock and Doc Cochran – and let’s face it, those guys are maniacs. 4 points.

Schemes - Scope: Survive, run a profitable business, get your town annexed to the USA. Modest, if impressively focused. 1 point.

Schemes - Complexity: Al plays the long game better than just about any villain I’ve seen, except perhaps Cersei Lannister. 4 points.

Overall Badass Rating: 20

As always, if there’s a villain you’d like to see put through The Machine, let us know in the comments! You can catch up on all the previous villainy here.

Next month: Dolores Umbridge

Art, as always, by Caspian Whistler.