Supernatural Top 15 Bad guys, Part 3

Continuing the Countdown

I am here to continue my top 15 countdown with the next 3 “awesome” bad guys to come out of Supernatural. Reaching the top ten, I had to really sit down and think how to rate them. This top 10 comes down to not only deplorableness of their actions; but also just a personal preference of who I really enjoyed watching be the antagonist week in and week out. And it is so hard narrowing it down. It almost hurts me sometimes to leave a character off the list. Not having the character who took out Kevin Freaking Solo or the Styne family who killed Charlie is a bit of a travesty to me. I console myself by saying they are in the top 20.

      Top Supernatural Villain #9


I will FOREVER be grateful to the Cain/Mark of Cain storyline because it brought this amazing video to life here. For those of of you who haven’t seen the Mark of Cain parody yet, your life will not be complete until you do. Watching demons twerk never fails to cure anything negative in your life. Plus watching the supernatural cast dance at the end will make you never ashamed to bust a move again. But back to bad guys and not awkward dance moves. Cain was introduced midway through season 9. Dean and Crowley pursue him as a lead on the blade they were looking for to kill Abaddon. However, the person they find was definitely not the schmuck they were anticipating. Or that Dean was anticipating anyways, I am quite certain that Crowley knew who would be there the whole time. Thus, here introduces the character of Cain.

Cain: father of Murder, brother to Abel, and the Founder (former leader and trainer) of the Knights of Hell. Played by one of my all time favorite actors in Tim Omundson, his portrayal elevated the character to fan favorite.  This is despite him only appearing in two episodes. Introducing Cain seemed like a no-brainier for Supernatural. It is the original sibling rivalry story, known by just about everyone. Supernatural loves its parallels and this delves into things that were going on in the Winchesters arc at that time. This show loves to add its own twist to famous mythologies, and in this case, we learn what the reason was that Cain killed Abel. Cain’s legend begins when he makes a deal with Lucifer, who was attempting to sway Abel to his side. Also we learn that the Winchesters are actually direct descendants of Cain.

Cain, who loved his brother very much, was unable to accept watching his brother become a demon. Lucifer and Cain struck a deal, Cain’s soul in Hell and Abel’s in Heaven. Cain slayed his brother in order for the deal to be sealed. Cain became the first Knight of Hell to save his brother (So. Many. Parallels. No?) Knights of Hell were recruited by Lucifer and trained by Cain, and significantly more powerful than most demons. They were considered invulnerable to most demon weaknesses and only killable by use of the First Blade. Devil’s traps would hold them, but not render them powerless.


As one of the oldest demons to appear and the first Knight of Hell, Cain is an extremely powerful demon. Cain killed other demons with a mere touch, which is normally reserved for angels. He could even prevent Crowley, the King of Hell and a powerful demon himself, from escaping and speaking just by a simple gesture. When the Winchesters, Castiel, and Crowley faced him in battle, he was unaffected by everything they tried against him (including angelic white light smiting power) except a devil’s trap and the First Blade.

Cain retained much of his humanity, which made him unique among demons. He loved a woman named Collette and when Abaddon killed her, he stepped away out of love for her memory. Demons aren’t known for their sense of honor, and Cain had honor. Crowley and Dean find Cain on an isolated farm where he was living a simple farm life and apparently beekeeping. Cas would have jumped at the chance to lead that life. Cain became isolated out of respect of his late wife’s wish that he no longer kill; honoring that wish for over a century before Dean came. Giving Dean the Mark, the deal was that Dean kill him with the first blade after he had disposed of Abaddon. At the end of the episode Cain eliminated an army of demons that were coming to kill Dean and Crowley, thereby breaking his vow of no more killing.

Crowley is so done with Demon Bullshit. Another reason to love Cain he pissed off Crowley
The reappearance of Cain in the series comes in Season 10. We find out that Cain has fallen back under the Mark’s influence, and is systematically eliminating his bloodline. This is another way his weird honor comes into play, sure he may be murdering by the hundreds but if you weren’t on his bloodline list you were safe from slaughter. Very complicated for a murdering bad guy. He honestly thought he was doing the world a favor by eliminating parts of his bloodline.
Dean: Your bloodline is tainted, so you say.
Cain: So I know. Not all killers are my descendants, and not all my descendants are killers, but enough are. Enough for me to know that extinguishing them is the least I owe this world. Can you honestly tell me that humanity is not better off with a fewer Tommys, a fewer Leons, a fewer yous?”
Cain also in “The executioner’s Song” attempted to kill dean, because in a weird twisted way he actually cared about Dean. He was trying to spare Dean the act of killing his brother. Cain saw Dean living out the crucial acts that made Cain what he was in reverse.
Cain: It’s been too long. That old feeling, makes me wonder how I ever had the strength to resist. This may be hard to believe, in light of what I’m about to do to you, but I care about you, Dean. I truly do, but I know I’m doing you a favor. I’m saving you.
Dean:Saving me from what?
Cain:From your fate. Has it ever occurred to you? Have you never mused upon the fact that you are living my life in reverse. My story began when I killed my brother, and that’s where your story will inevitably end.
Dean:No. Never.
Cain: It’s called the Mark of Cain for a reason! First, first you’d kill Crowley — there’d be some strange mixed feelings on that one, but you’d have your reason, get it done, no remorse. And then you’d kill the angel Castiel, now that one, that I suspect would hurt something awful. And then! Then would come the murder you’d never survive, the one that would finally turn you into as a much of a savage as it did me…
Dean: No
Cain:Your brother, Sam. The only thing standing between you and that destiny is this Blade. You’re welcome my son.
Twisted twisted sense of honor and caring from a demon. It was truly an amazing episode overall one of my favorites from season 10, and probably in my top 15 overall. Cain eventually died in this episode, stabbed by Dean with the First Blade. We knew at this point he had a death wish at one point. It’s unknown if he did at this point in time. Sadly beaten in the end because of ego, Cain thought he was superior to everyone and underestimated the combined might of Sam, Dean, Castiel and Crowley. Arrogant when it came to the fight, and probably rightly so given his past and reputation in the demon world. He left himself open though after taking the First Blade from Dean, Dean steals Cain’s knife and slices off his hand. He then stabs Cain with the First Blade after Cain admits that he can never stop trying to remove the taint from the bloodline. A sad end to a complicated character. I miss Cain and his epic hair.
Rock on with your fabulous hair

Top Supernatural Villain #8


      This chick was mental. And I loved it. After getting a getting a slightly underwhelming main female bad guy in Eve; it was refreshing to see Supernatural get a female villain right. Abaddon was a BAMF who took no shit from anyone.
“You’ve been very entertaining, my dear. But I don’t need your permission. Abaddon takes what she wants. And right now, she wants everything.

     Abaddon literally burst into the Winchesters life in season 8, when she chased their Grandfather Henry Winchester through time from 1958 to 2013.  She took possession of a woman named Josie Sands, a secretary for a secret society of knowledge and magic. She nearly wiped them out, leaving one person alive to chase Henry through time. When she did that, everyone had assumed she was dead seeing as she jumped almost 60 years into the future. She was oftentimes a kill first question later type of demon.

     Abaddon is the first Knight of Hell the boys encountered, having not met Cain yet. So they were unaware that she was immune to many of the traditional demon killing methods. Abaddon is untrustworthy, greedy, and quick to anger/violence. Despite that though, She is very sly and cunning.  She adapts quickly, managing to use modern technology, weaponry, and armory to her advantage despite not having been around these things for very long. Some of that is probably the demons ability to access their hosts memories. She is a brilliant strategist in the long run. The character has a sadistic and twisted sense of humor, and extremely power hungry (even for being a demon.) Her ultimate end goal is to not only take over Hell but to make all of mankind and Heaven bow to her will as well. Talk about being ambitious.

     Although Abaddon enjoys causing suffering to others and revels in creating fear in her victims, she often will kill her victims in quick, brutal ways. She views killing as “art.” Weirdly though, she saw the act of killing her victims quickly as merciful, as opposed to torturing them over a longer period of time before taking their lives. The fact that she used torture to interrogate hunters in the episode “The Devil May Care” despite being telepathic suggests that Abaddon was either teaching her minions better techniques for torture, indulging her sadistic side, or a combination of both. I go for both, this bitch was crazy.

Her first episode she manages to destroy the MOL, kidnap Sam, and kill Henry Winchester in front of his grandsons. Which alters the whole course of the Winchester history. Now back in 1958, a young John now thinks his father has abandoned him, seeing as how he didn’t know he was murdered in the future. Who knows what would have happened had Henry made it back and raised John as a MOL, would he have still had Sam and Dean? Yes, as him and Mary were brought together by Cupids, but, the way they went about fighting things would have been different clearly having the knowledge of the MOL. At the end of the episode she was trapped by Dean with a devil’s trap bullet in her skull, dismembered and her body parts buried in different areas since the boys had no idea how to kill a Knight of Hell.

Not creepy at all right?

She makes her return at the end of Season 8, when during the course of doing the Trials to close the gates of hell, they need a Demon to cure. Sam and Dean discovered the old bunker that had been hidden by the MOL. In there, they find video of the MOL successfully having turned a demon human with a ritual of injecting sanctified human blood into the demon over an 8 hour period. So now, stuck in the situation of literally no demons on earth (As Crowley has them all locked down) they dig up Abaddon. Put her back together minus her hands and are set to begin this ritual. The ritual gets interrupted; and she uses telekinesis to make her unattached hand come dig the bullet trapping her out of her skull and off she flees. Did I mention BAMF?

Crowley tries to summon her for help when Sam is performing the purification ritual and instead comes to kick the shit out of him. Sam ends up dousing her in holy oil and lighting her ass on fire. For all they know she is gone. She is brought back to life by loyalists and the war for control of Hell begins. Abaddon kills some hunters at the beginning of season 9, to try and lure Dean and Sam into a trap. She then goes on a crusade to recruit demons and put them in “elite” vessels. She is completely disgusted by the fact that some demons are possessing elderly bodies. Abaddon believes that a worthy King fights and conquers. She has shown immense disdain towards Crowley’s methods. She views him as an inadequate King because he is most concerned with contracts. Abaddon does not care about the politics of deal-making.



Abaddon goes on a tear. She steals hundreds of souls to create an army of demons loyal only to her and there are places that this is happening all over. She has coerced Crowley into working with her by stealing his son from the past and holding him hostage here in the present. Alas, in the end, it didn’t matter, her arrogance once again cost her victory. She underestimated Dean and the power he had over the Mark of Cain. Dean killed her by stabbing her with the First Blade. And so ends the Knights of Hell’s campaign. But damn if the choices Dean made to take her down didn’t have consequences of epic proportions.

Top Supernatural Villain #8


Demon Bitch of Epic proportions. First Character on the list to be portrayed by 2 different actresses. Personally, I am a fan of the first Ruby over the second. I thought she hid the manipulations of Sam and Dean better, but both did a great job in playing this utter bitch. She enters the series at the beginning of season 3 after having escaped from Hell, and tries to pass herself off as a hunter. Ruby comes across as a “helpful” demon, remembering what it was like to be human. Ruby wishes she were evil through and through like other demons, then they wouldn’t view her as scum. With the reveal of her real motivation, it’s not clear if Ruby meant any of it. She is addicted to french fries, which is strangely human for a demon.


At first, Ruby formed an alliance with Sam by promising to help him get Dean out of his deal.  After this failed when Dean died, she stayed with Sam and started training him to defeat Lilith. This marked her as a traitor of hell and she became hunted. Calling her a bitch, slut, whore yada yada really gets on her nerves, which is probably why Dean and the other demons keep doing it. Being such a manipulative bitch, She gets pissed off when people don’t do as she expects, interfere with her plans, or do something she considers incredibly stupid instead of going with her suggestions. Finally, don’t hit her unless you’re too powerful for her to hit back. Since Dean has a habit of doing all of the above, Dean is not Ruby’s favorite person. But I loved the 2 of them bitching at each other back and forth.

I loved Katie Cassidy’s sassy, tough, bad-girl portrayal of Ruby. I hated that Ruby had bit it. And I doubt she was welcomed back to Hell with open arms. Traitors usually aren’t. Though Ruby works mostly with Sam, her snark is oh-so-Dean-like. A sampling:

Ruby: “It’s called witchcraft, shortbus.”

Dean: “But you’re a demon.”
Ruby: “Don’t be such a racist.”

Bobby (after he shoots Ruby): “What do you want?”
Ruby: “Peace on earth, a new shirt…”

Ruby’s rampant slaughter of other demons, her working partnership with the Winchesters, and her ongoing rebellion against Lilith, don’t win her any brownie points with Hell. Alastair seems to think that she doesn’t even deserve to be called a demon anymore because of her protecting Anna (an angel) in “Heaven and Hell”.

When Bobby was trying to restore the Colt’s power after Dean used its last bullet on Azazel, Ruby arrived and baited him into shooting her with the defective gun. She helped him fix the Colt and he later brought it to Sam, who killed two demons with it to protect Dean. She became irritated when he questioned her motives in helping them, and threatened to take the Colt from him and help someone else. Sam pointed the gun at her but did not shoot when she reminded him that she could help him save Dean. She reminded him that they were in a war and there would be “collateral damage” and he would have to resist his gentle nature – but that she’d be there for him. She proved this by helping him against witches in the episode Malleus Maleficarum, saving both Sam and Dean from witchcraft.

Later on, Ruby and Dean had a heart-to-heart in which she confirmed that he too would eventually become a demon (which became one of his deepest fears). She admitted that she had lied to Sam so that he’d listen to her; No one could save Dean from Hell, but she wanted his help in preparing Sam for fighting Lilith once Dean died.

She appears again in “Jus in Bellos” to try and save the Boys from an army of demons Lilith sent to destroy them. She suggested that they kill the virgin to use her heart in a spell that would kill the demons laying siege to the police station. This didn’t go over well with Dean. In spte of the fact the spell would also have killed Ruby. Despite her and Nancy’s willingness to sacrifice themselves, Dean vehemently refused her offer. After he gained the support of Sam, who was more open to the idea, Ruby gave up in disgust and left. The brothers escaped by using a mass-exorcism, but Lilith had killed everyone in the station after they left.

Lilith sends her back to Hell and takes over Ruby in order to trick Dean and kill him. You discover in season 4 she is not only alive but has tightened her hold on Sam while Dean has been gone. She manipulated Sam into drinking demon blood to increase his powers. With Sam now more open to her advice due to his grief, Ruby gets him to the thought that he avenge Dean’s death by killing Lilith with his psychic powers. She persuaded him to train with his abilities, before actively going after Lilith immediately. During this time, Ruby apparently stopped him from drinking alcohol heavily, started a sexual relationship with him at his lowest point, and became his hunting partner in Dean’s stead. Her best moment as a fake good guy came from getting the Demons and the Angels to fight each other over Anna in “Heaven and Hell.”

Ruby’s words to Sam about getting between Heaven and Hell gave him the idea of bringing both sides together to fight each other. She put herself in harm’s way, exposing her location to Alastair, who denounced her for protecting an Angel. Alastair tortured her with her own knife until offering to take Alastair to Anna. Alastair fought Castiel and Uriel, who had been lured there by Dean. Battle fought, their side came out in victory. After this Ruby begins to pull back from Sam sending him into withdrawals from demon blood. He can’t even see she has turned him into a blood junky.  They reunite and she finally tells him that he is strong enough to defeat Lilith. A horrible fight between Sam and Dean occurs when he finds Sam with Ruby. He betrays Dean to side with Ruby.

Her character was revealed in the end though. After Sam killed Lilith and released Lucifer, her master plan is revealed. In a villain monologue she reveals that she was working with Lilith. No one except Lilith knew and that made her awesome. In this scene the fact that she had grown to care for Sam in some regard came through. She honestly thought that this had been for Sam’s best interest. Ruby rubbed in the fact that Sam never needed to consume demon blood. She referred to him as Dumbo, saying he never needed the feather to fly. The blood that Ruby gave him was just to strengthen his vessel, so Lucifer could possess him after he set him free from his cage. Finally, she promised him that Lucifer would reward her and Sam for their service, and she expressed the hope that they would continue working together.

Her hopes were soon dashed however when Sam willingly held her down and let Dean stab her with her own knife. Clearly the betrayal was stronger than whatever feelings Sam had harbored for Ruby. Good Riddance you manipulative Bitch.

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