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Part 1: The Good, The Bad, And The Crowley


            The man who became a demon. The demon who became a Ruler of Crossroads. The Ruler of Crossroads who became the King of Hell. Crowley’s rise to power has shown one thing to be undeniably true - he’s a survivor. Whether you’re a fan of his or not, on several occasions he’s stepped in to rescue the Winchesters, helped defeat ‘big bads’, and even saved Castiel’s life. Yet, in all fairness, he asks for nothing in return. At least, not right away. He does these things because he feels it will give him an advantage. The game he plays is quid-pro-quo, but he’s also not above rotating the chess board. There have been plenty of dark deeds the King of Hell has performed as well. While his allegiance to the Winchesters can appear to change with the tides, his devotion to himself has never faltered. Which leads us to an interesting conundrum: Do we call someone who has inarguably helped and supported our main characters, yet serves primarily himself - a hero or a villain? How do we crack the code that is Crowley?

“You do want to conspire, don’t you?”

            Since his introduction, Crowley has been set forth as someone who can’t be trusted, yet the advantages that come with having him as an ally can’t be denied; something, mind you, that he, himself, is well aware of. To that end, one thing the Demon King loves to do is ally himself with virtually everyone. In fact, one of Crowley’s greatest strengths is recognizing potential enemies and using any knowledge of them to form alliances.

            Upon first meeting them, he was quick to secure a working relationship with the Winchesters, offering them a weapon that could kill even him. A necessary move on his part considering he believed this would be his only opportunity to gain their trust.  He was more than prepared for that first encounter with Sam and Dean, Colt in stow and bargaining chips already on the table, knowing they’d track him down sooner or later. Always, he is three steps ahead and two steps sideways, giving a whole new meaning to “know thy enemy”. The Ruler of Hell doesn’t just learn about his opponents to find ways to defeat them. He uses that knowledge to seek ways of making himself seem invaluable to them. It’s a neat trick that has kept him alive while deep in the company of what should be fatal adversaries.

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            Considering with whom he’s formed alliances, you’ll quickly find this Connoisseur of Contracts spares no expense in the company he keeps. In terms of the Winchesters, there are no hunters better. Crowley doesn’t care that they’re ‘good’, or that they’d kill him first chance they got. If you’re the best at whatever it is you do, then Crowley wants in. He chooses people based on their power, not whether or not they share his ideals. If a big bad, or a big good, ever comes into town, you can bet the Lord of Paisley Ties will be there with a deal to sweeten their liking of him. He did this with Castiel, Rowena, Naomi, and even Ramiel; and tried it with Dick Roman and Amara, though to no avail. If you’re a potential enemy, then you’re the perfect candidate to be an ally. That’s how he sees it.  There’s no mistaking his prowess when it comes to judging who will be a good partner and who will make a worse adversary.


            Crowley’s strongest skills are his abilities to keep people happy who would normally want to kill him, and his strongest weapon is his knowledge of those people. Ever resourceful, he’s the only demon that we know of who is not part of a royal bloodline to wear the Crown of Hell. Ramiel was presented as “next in line”, along with his siblings. Hell’s Crown is not something that is fought for and earned. It’s passed down through family. Yet, along comes this Master of Deals, who obtains it for himself simply by choosing his ‘allies’ very carefully. Though Hell had sent him to retrieve Ramiel, he came prepared with gifts, ready to begin what he likely anticipated would be a long endeavor of kissing up and brown-nosing to win over the Yellow-Eyed Prince. Viewers can decide if Crowley had already suspected Ramiel didn’t want the crown, which is what I argue. Playing the hand he’s been dealt is never Crowley’s move. He’ll always try to stack the deck. Crowley is not a warrior. He’s not a soldier. He’s barely even a fighter. So, whenever there’s a threat, he’ll cross every line possible to avoid being in a fight and seek ways to undermine or ‘befriend’ potential enemies to ensure his survival.

“Right now, I’m the goodest guy you got.”

            When you think of Crowley, “good guy” probably isn’t what comes to mind. It’s easy to see the red eyes and torture and villainous ways, and say: “He’s immoral, I don’t like him.” But, it’s equally important to see the things he doesn’t do, as well. Reading between the lines can be tricky. On the one hand, we can say Crowley is a demon who makes deals to gain power and be evil. On the other hand, we can choose to acknowledge that while he makes these deals, he has, in fact, never gone back on a single one. He takes his deals very seriously. Keep in mind, there’s such a thing as fine print, and this Demon Extraordinaire will use that, like everything else, to his advantage. Such was the case in his deal with Bobby. So, maybe you think he lied when he made a deal or didn’t follow through with what he said. But, in truth, he was actually more careful than you realized when he made the deal in the first place. This isn’t to say that he never lies or cheats, but when it comes to his contracts, they are his pride. It’s as simple as that.

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            In addition, there are his feelings for himself to consider. Deep down, Crowley believes he deserves to be loved (as he bellowed while addicted to human blood), but not because of some self-proclaimed eminence. Because, unlike everyone else, he knows all the times he’s opted not to hurt or kill potential enemies; he knows the attention and care he puts into each of his deals; he knows how lucky people are that it’s him in charge, and not some other powerful demon; he knows he is NOT evil, just willing to do evil things to achieve his goals. Why shouldn’t we love him? Why shouldn’t we think ourselves lucky it’s Crowley and not Lilith, Azazel, or even Ramiel, wearing that crown?


            That which Crowley does not kill, can potentially make Crowley stronger. He doesn’t really care much for killing. Not because of morals, mind you. Killing is just so … permanent. Only those he ultimately fails to ally himself with, despite his best efforts (Lucifer, Dick Roman, Abaddon, Amara), are the ones he seeks to kill. But, with regards to the Winchesters, for example, killing isn’t on the table. Even if they cross him (Sam shot him point blank, Dean held him captive, and Castiel betrayed him during their deal for Purgatory), he manages to find reasons to spare them. Crowley understands why they treat him the way they do, because he would do the same. Besides, revenge and arrogance aren’t really his style. In fact, it’s the ones who blindly worship and obey him that he has virtually no respect for, like his demon henchmen. He treats them as servants but sees Sam, Dean, and even Cas, as valuable allies and even worthier adversaries. Their existence makes his own worthwhile.

Crowley Essay

            Also, keep in mind that ‘evil’ is something Crowley puts on like a good suit. He can play nice when and if the occasion calls for it, or he can play dirty, if that’s what it takes. It’s important to realize, however, that none of these behaviors are his true self. Deep down, The Keeper of Hell’s Keys cares about only one thing: himself. For someone who takes no sides, he, in actuality, has very few enemies. At the same time, he likes to boast he has no friends either; something of a point of pride for the Hellhound Honcho. He doesn’t choose the good side, or the bad side; he chooses his side. He bears no special pride in being a demon, either; hardly ever showing off those bright red Crossroads Eyes of his. Plus, just thinking of his ‘kingly duties’ bores him. In fact, one of his first actions as king was transforming the Realm of Torture to create a line in which people would have to wait for all eternity. In its own right, it’s still torturous, but it’s also a very hands-off approach. Keeps him from having to always be there. Hell runs itself now. He much prefers to be involved as little as possible when it comes to actually being King of Hell. All that really interests him is the power that comes with it since that’s what helps him to survive.

“You’re good. But, I’m Crowley.”

            So, how does this help us decode the Bearer of Hell’s Crown? Despite the numerous times Crowley’s aided the Winchesters, he’s been more of an obstacle than anything. Consistently, he’s been a thorn in their side, opposing them, and creating despair along the way. Thusly, it seems most fitting to label the Former Ruler of Crossroads as an antagonist. However, more often than not, the outcome of all his input is positive. So, by definition, he is a type of hero, but only in so far as supporting others. He never sets out to do any good on his own. In fact, I think the King of Hell would be quite insulted to be called a hero. After all, he never hesitates to remind people just how wicked he can be.

Crowley Essay Drinking

            But, what if we narrow our focus even further to consider just Crowley’s role in the story? Meaning, let’s remove all other arcs and follow just his arc; paying attention to only his episodes and developments. In his world, he’s the one driving the story. But, he’s still a villain. You’ll find the trope that best describes him is actually Villain Protagonist. A popular example of this is in the show The Blacklist, where the main character, Raymond Reddington, is an admitted criminal who murders, lies, and cheats on a daily basis. The people he hurts typically deserve it, however. Crowley parallels this character fairly well. He’ll commit any crime necessary and display virtually no morals in order to achieve his goals. The slight difference is that Crowley will kill innocent people (such as Kevin’s girlfriend and all the would-be prophets) as well as those who deserve it to satisfy his means. Then again, unlike Reddington, Crowley is a demon, which should be taken into account when judging the choices he makes and the things he’s willing to do.


            Yet, if we continue to delve deeper into his psyche by removing the TV show entirely, even his own arc, we are left with just the man - just Crowley himself. Who is he? Regardless of whatever situation he may be in or experiences he may have, how should we expect Crowley to react, behave, and think? Firstly, it’s important to note that usually a single character can fall into many tropes. I’ve seen Crowley labeled from main antagonist to anti-hero. I’d even go so far as to say he sometimes exhibits traits of a Code Hero, or Hemingway Hero, if you prefer. This type of person lives life to the fullest, because for him, death is the ultimate end to things. He’ll do whatever it takes to survive but follows his own code and set of morals in the process. Merle Dixon, from The Walking Dead, could easily be seen as a type of Code Hero. They deem what is acceptable based on their own point of view in life. Crowley very much aligns with this type of personality. Yet, it doesn’t describe him fully. Even the trope of anti-hero only covers certain aspects of him. In truth, anything under the category of ‘hero’ will only be a partial assessment. Remember, half his wardrobe is Good Suits. The other half is Evil Suits. Crowley dresses himself accordingly. But, underneath it all, he is a demon. So, something with ‘hero’ in the title just won’t do for this Purchaser of Souls.


            So, what then is the final verdict? Well, according to, there is a label for someone who’s “desired ends are mostly good, but their means of getting there are evil.” This type of person is “more good than normal villains, but not quite heroes, blurring the line between hero and villain the same way an Anti-Hero does, but by coming from the opposite direction. … Despite this humanizing characterization, they are rarely less dangerous. … Most of them are well aware that what they’re doing is ‘evil’… but strive to maintain a facade of good PR. They’ll see it as a viable means to a (possibly) good end.” And that, right there, is our beloved king, Crowley. This wonderful trope is called Anti-Villain. Standing on his own, Crowley is someone who will play either side, but whose motives are always purely selfish. He isn’t evil simply for the sake of being evil, has no interest in world domination, nor is he interested in vanquishing the world of all that is good. Despite being a demon, he has and will align himself with ‘good’ people in order to achieve his own goals, securing him as a textbook Anti-Villain. As a matter of perspective, if you were to remove Crowley from Supernatural and pluck him into any other TV show (Dr. Who, Firefly, Warehouse 13, Leverage, Battlestar Galactica, 24, Charmed, X-Files, etc. See what I did there?), he would still be the Anti-Villain. It matters not his surroundings nor experiences. This is who Crowley is, at his very core.

Now, if you’ll excuse me, I have a little hell to raise.”

            Like General Zod from Superman, there are just some villains who earn their place against the heroes of a story. Just as I would humbly ‘kneel before Zod’, had it ever come to that, I would also not be ashamed to ‘bow before Crowley’. As worthy adversaries, these villains deserve their victories. Like bowing to your opponent before sparring martial arts, there is a prestige and a humility that comes with respecting your enemy. Crowley has earned his place as Villain in our story, despite his apparent fondness for our heroes. He IS my king. Our king. A king that deserves the respect that comes with fear and power. And, while he may be best defined as an anti-villain when considering his layered and complex personality, rest assured that brings him no closer to being a hero. To consider him such would almost be a disservice to his character. He is, after all, Hell’s King. Crowley likes things the way they are. As a villain, he gets to call the shots, bend the rules, have minions, and answer to no one. He’s worked hard for his status and earned every penny of it. Despite the occasional kill-me-now expressions he bears while having to actually be a king to his Kingdom of Demons, this Soul Collector has far too much fun wheeling and dealing, wining and dining, and selling “sins to saints” than he ever would if he had to be one of the ‘good guys’.

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            Make no mistake, underneath that fine tailored suit and suave English accent, is a demon who would kill you no sooner than snap his fingers, who has had only one thing on his mind since we’ve met him - survival. The power that he holds demands our respect and attention. He knows he’s the biggest gun on the wall to reach for in a fight and will use that as leverage every opportunity he gets. Keeping him as an ally-at-arm’s-length is the best asset you could have. He’s not interested in being your friend, emotions are weaknesses, and he’ll avoid being your enemy - he knows his odds of survival are better with you than without. It’s that magical place in the middle where he’ll ask you to trust him, know that you won’t, try to stab you in the back just for sport, and hope you’ll put up a good fight in the end just to make it all worthwhile that Crowley likes to be.

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            Please understand that I award him this title of Anti-Villain not out of any dislike for the character or lack of emotional connection. In fact, it is quite the contrary. I adore Crowley for being precisely who and what he is. I won’t dare push off any of my own personal ambitions or idiosyncrasies on him. He has plenty of layers and depth already. Concerning Crowley, it is important to keep this in mind: Heroes do not make the story great, villains do. Heroes only make the ending great. But, a story earns its greatness by the obstacles it must overcome; by the villains that make it possible.

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