Saving people. Hunting things. The family business. For Supernatural’s Sam and Dean Winchester, that’s the story of their lives. The brothers spend their days hunting monsters. Vampires, werewolves, wendigos, wraiths, ghosts — you name it, they’ve killed it. The formula usually involves the Winchesters discovering a mysterious death or disappearance, suiting up as fake FBI agents, investigating the lore, then killing said monster. That’s how most Supernatural episodes unfold.
However, also happening in between the monster of the week fun is the season long arc that features the brothers fighting a more powerful monster, who has an army of minions working for him or her. It takes Sam and Dean several episodes to figure out who they’re after, then they must fight a few henchman before they can find the special weapon or spell that works on that season’s villain. Obviously the brothers always win, but some big bads are so much fun, viewers are sad when it’s time for the big death. There are also a few adversaries who have been so good, they lasted for years, practically becoming part of the family. To remember all the brave demons, angels, leviathans and kings of Hell who’ve given their lives, here are the major Supernatural villains ranked from worst to best.
As the lastest demon running Hell we still don’t know much about Asmodeus. He is a Prince of Hell whose siblings are previously seen antagonists Azazel, Dagon and Ramiel. The lore says that a Prince of Hell was created by Lucifer and are his heirs.
As the last remaining Prince of Hell, Asmodeus has taken control of Hell and is obsessed with finding Jack, Lucifer’s son, and bringing him into the fold.
So far we haven’t seen much of his abilities past disguising himself and killing, but obviously he has a bigger plan since he wanted to raise an evil army of monsters. Since it’s still early in the season, it’s possible that Asmodeus isn’t the real big bad and is just a placeholder. Compared to the rest of the list, we’re in “wait and see” mode on him.
24. GORDON WALKER
Before he was breaking hearts on This is Us, Sterling K. Brown was literally ripping them out as hunter Gordon Walker. During season three he first befriended, then hunted the Winchesters. Gordon was a brutal hunter who killed anything non-human without any consequence. At first Dean was ok with this plan, but then he quickly realized how unhinged Gordon really was.
Soon Gordon was obsessed with the idea that Sam was evil and he was on a mission from God to kill him. He chased Sam and Dean across the country and turned other hunters against them. Ultimately, he was turned into a vampire and Sam decapitated him. Though he was just human, Gordon was clever and facing off with someone who knew everything they did was a challenge the brothers weren’t quite ready for at that point in their careers.
Sam and Dean have spent their entire lives fighting monsters and learning about magic. They’ve learned how it can be misused by the wrong people, but they didn’t know there was a market for it until they met thief Bela Talbot. During season three she stalked the brothers and stole from them during jobs so she could sell items on the black market.
It turned out she was really looking for a way to get out of her own deal with Lilith, which she failed at.
She was last seen waiting for Hellhounds to come get her, so in the world of Supernatural she could return as a ghost or demon. Of course, actress Lauren Cohan is a little busy with zombies right now. She was more of an annoyance than anything, but her constant meddling put the boys in danger time and time again.
22. SAMUEL CAMPBELL
There’s so much focus on Sam and Dean’s Winchester side of the family, it’s easy to forget that their mom Mary is also from a family of hunters, the Campbells. In season six, we finally got to meet them when Sam teamed up with them for a year when he came back from Hell. They weren’t quite as analytical about hunting as the Winchesters. Led by Samuel (Mitch Pileggi), the Campbells’ motto was to pretty much kill anything that moved. Dean didn’t trust their methods and it turned out he was right.
Samuel was actually working for Crowley, because he promised to bring Mary back from the dead. Despite Dean’s pleas to help them and not trust Crowley, Samuel betrayed the boys and burned any family bridge they had left. He was killed while hunting a monster and no one seemed very broken up about the loss.
In season ten, Dean became afflicted with the Mark of Cain and it slowly turned him evil, filling him with a murderous rage. Though Sam and Dean spent the whole season looking for a cure, there seemed to be no way to fight the inevitable. In their quest to find out more information, they discovered Cain himself had fallen back into killing people after years of fighting the Mark’s power.
Things culminated in a battle between Dean and Cain, with Cain telling Dean there was nothing he could do to get rid of the Mark.
For being so central to the season’s story arc, the reveal of Cain was actually very anti-climatic. With all his power, he lost to Dean in a fist fight. It also didn’t help matters that this may have been the series’ weakest season.
When it comes down to it, Alastair is really just a very powerful demon. He’s Hell’s greatest torturer and used his skills on Dean while he was trapped there. What makes him truly dangerous is he doesn’t just cause physical pain, he also gets inside his victim’s heads. He was able to turn Dean in Hell and get him to start torturing others.
Once he made his way upstairs, he joined the plan to break the seals and free Lucifer. He tried to kill fallen angel Anna and ended up breaking the news to Dean that his activities in Hell had broken the first seal. His tenure may have been short, but it was impactful. It would be interesting to see what alternate reality Alastair is up to and what his role is in that universe.
19. THE STYNE FAMILY
During the endless quest to rid Dean of the Mark of Cain, the brothers discovered a powerful spell book called The Book of the Damned. They thought it would be the secret to finally curing Dean, but it turned out it attracted the attention of the crazy, murderous Styne Family.
They had been using it for years to build their power, but apparently lost it. Once Charlie found it, she couldn’t shake them.
The Styne Family had been living for years using various dark spells, including chopping up others and using their organs. Their worst moment came when they killed Charlie. They were a truly despicable group of people who deserved the epic massacre they got from Dean. Well all of them except for that one kid.
The Winchesters have encountered countless evil angels over the years. One of the most unexpected was Naomi. Played by Stargate’s Amanda Tapping, she appears in season eight as the angel who saved Castiel from purgatory. She reveals herself to be the head of Heaven’s intelligence division. She controlled Cas, making him lie to Sam and Dean and brainwashed him into killing hundreds of Dean clones.
When Cas broke free she killed dozens of innocent people just to get him back. Like all the other rogue angels she claimed it was all for the greater good, but all the death and chaos was really about protecting her own agenda of retrieving the angel tablet. Her millenia of experience kept her a step ahead of Sam and Dean, but as usual it was her single-minded focus and mistrust of the brothers that led to her downfall.
In all the monsters they’ve fought, Sam and Dean never wondered where they came from. When Crowley began torturing monsters to find purgatory, Eve, the mother of all was released to protect her children.
Once she was back from purgatory, she could control every monster and basically see through them.
The boys had to travel back to the old west just to find the ashes of a Phoenix, the only creature that could harm her. When they tracked her down she had turned a whole town into new hybrid monsters that could blend in and go undetected. She was even able to power down Cas. Her impact only lasted a few episodes, but it does leave behind the question if there was a mother of all, was there a father?
In season four when the brothers first started dealing with angels, it seemed like a good thing, as they now had powerful allies. In actuality they just had even more powerful enemies to deal with. It seems Sam and Dean had pivotal parts to play in the destined battle between Michael and Lucifer, and the angels were meant to ensure that would happen. The one in charge of keeping the boys in line was Zachariah.
He sent Dean to the future to see how bad things get, he chased them through Heaven and then used their brother Adam as Michael’s vessel.
Though he believed everything he was doing would lead to paradise, he had no qualms about how far he would go to fulfill destiny and ultimately he met the fate of all monsters who cross the Winchesters too many times.
Whenever demons appear as children, you know extra bad things are about to happen. The boys heard whispers of a dangerous new leader in Hell long before they met Lilith. She planned to break the 66 seals keeping Lucifer in his cage. The problem was the brothers couldn’t fight her and all her minions at the same time. Her plan was so expertly executed, they really couldn’t match it with one of their own.
She even found a way to come between Sam and Dean so they wouldn’t be strong enough to stop her. Turns out the one thing she didn’t account for was that her death was the final seal. Though she died, her plan worked and Lucifer was released. She just wasn’t there to see it.
There’s an argument to be made that Azazel could be at the top since he’s the demon that started everything. Azazel made the deal with Mary that allowed him to return in ten years and enter Sam’s bedroom. He’s the one who feeds Sam demon blood, which makes him strong enough to be Lucifer’s vessel.
It is in this moment that Azazel kills Mary and sets John on the path of hunting and training his sons to be hunters.
No matter how much time travel and flashbacks the show gives us, it’s these events that shape Sam and Dean’s entire lives. Losing their mom and being raised in such a dysfunctional manner is the root of all the brothers issues. When it comes down to it, Azazel is the one who truly ruined their lives.
While most demons are out to kill them, there are a very few who Sam and Dean let live because they are occasionally useful. One of those was Meg. In seasons six and seven she was almost a full-fledged member of Team Free Will, however, before that she was still completely evil and did terrible things in the name of her loyalty to Lucifer.
Meg was Azazel’s “daughter” and her only focus was to serve him and his plan. She kills several of the Winchesters’ closest allies, is responsible for Bobby getting paralyzed and while possessing Sam, kills a hunter and tortures Jo. In an ironic twist, she survives through all of her worst crimes, but is then killed while helping the brothers escape from Crowley.
12. BRITISH MEN OF LETTERS
In season eight, through the magic of time travel, Sam and Dean meet their grandfather Henry, who was a member of a secret supernatural society called the Men of Letters. They discovered a bunker filled with books and history on monsters and magic.
Following the almost death of God, the British Men of Letters decided it was time to get involved and take over American hunting.
Though they had great success, their style was much more ruthless than what the Winchesters and their friends were doing. Their plan was to brainwash Mary and use her to track down hunters and kill them. In the end, the Americans led an assault on the Brits compound and let them know to stay out of their turf. Sam and Dean were essentially being attacked by their evil doppelgangers, who knew everything they knew but had none of their moral code.
Ruby was a run of the mill demon that had no special powers. What made her so influential to the Winchesters’ story was her ability to get in Sam’s head. From the moment they met she was manipulating him into being exactly who she needed. She started by separating him from Dean, then she pushed him to give in to his demonic tendencies, until she had him right where she wanted and Lucifer was free.
What made Ruby so hated by fans wasn’t the demonic havoc she caused, it was the rift she caused between Sam and Dean. A rift that has seemingly healed, but at the same time caused enough cracks that it led to future problems for the duo. She caused them a level of psychological pain that they are still dealing with in small ways.
As the last Knight of Hell, Abaddon may have been the most powerful demon the brothers have ever come up against. The usual methods just wouldn’t work on her. She also had a single goal, knew what it took to accomplish it and was ruthless in her ambitions.
There was no talking to or reasoning with Abaddon.
No matter how many times the boys thought they had the upper hand, she found a way to survive. Also, we got to know her host Josie, so it makes her possession even more heartbreaking. Like most antagonists, she grew to hate the Winchesters for being so involved in her business. When they finally did kill her, the cost was high, as Dean had to get the Mark of Cain.
9. ALPHA VAMPIRE
No matter how deadly or what their motivation, the boys can usually figure out how to kill the monster of the week. Frankly, for the familiar creatures the methods are normally not that difficult. However, every once in a while they run across the alpha version of a monster and that takes a special weapon, because “the really evil ones always need a special sword.”
A character that showed up frequently over the years was the Alpha Vampire. Rick Worthy’s charmingly, scary father of the vampires first appeared when he was captured and given to Crowley. He set the tone for what was to come when he was completely nonplussed about being tortured. Following Crowley’s purge of most of the alphas, the Vampire was pretty much the most powerful monster left until he was killed with the Colt by Sam.
One of Supernatural’s most interesting stories is its plot that angels are just one giant dysfunctional family dealing with their absentee father. Even before Sam and Dean stopped the apocalypse, there was non-stop infighting. Once Michael was gone, there was a new civil war in Heaven every season.
The only one that actually came close to working was Metatron’s attempt to take over and become the new God.
He did succeed in expelling all the angels from Heaven, of course things all went wrong when he involved the Winchesters. He was imprisoned in Heaven, but never came around and felt remorse for his actions. He returned to help fight Amara and surprisingly sacrificed himself, but he could never really be forgiven for having Kevin killed.
First introduced as a powerful witch being tracked by the brothers, Rowena has been a constant thorn in everyone’s side her entire tenure on the show. Though she seemed like just another villain Sam and Dean would have to eventually kill, a twist came when she was revealed to be Crowley’s mother.
That actually made her even more dangerous, as she now had influence over the king of Hell. Once she was back on Earth, she got possession of the Book of the Damned and gained more power. There really isn’t time to list everything she’s done and all the people she’s hurt, because it’s so many. In the season 12 finale she was killed off-camera by Lucifer, but off-screen deaths never stick on Supernatural and it’s likely that we’ll see her again.
As the oldest and most powerful archangel, Michael has no match in Heaven and Hell. In a weird twist, the brothers only had a few interactions with Michael, but they were all life-changing. Dean first encountered Michael in the past when he took over the young version of John.
This is when he found out that Michael could possess the whole Winchester bloodline.
Before Michael meets up with Sam and Dean again they must spend the whole season running from angels doing his bidding. Later, he appears for the battle using Adam as his vessel. Sam ends up trapping him in the cage the same time he traps Lucifer and remains there. However, we recently met alternate world Michael, who won the fight against Lucifer and wants to come to the main Supernatural world and take over.
Supernatural takes a lot of liberties with traditional bible stories. Perhaps the craziest thing they’ve done is make God unsuccessful author Chuck. This was part of the storyline surrounding the darkness Amara, who turned out to be God’s sister.
Chuck and Amara were the closest of siblings, but she became jealous when he created new worlds and kept destroying them. When he created humans, he decided to trap her so she couldn’t do the same to them. Unfortunately, Dean released her and she began her plan to destroy everything. She killed hundreds of people with her fog that turned them into crazed killers. In the end, she was just sad and lonely that her brother turned on her and Dean was able to reunite them and once again save the world. The two her last seen leaving this plane so they could work on their relationship.
Some Supernatural villains are too good to kill. Top of that list is Trickster. He showed up at least once a season to trap the boys in some crazy comedy shenanigans. The show can be such an emotional roller coaster, that it’s always a relief when the funny episodes come up on the schedule.
Anytime the Trickster is involved, viewers know it’s going to be a hilarious time that also moves the story.
From “Tall Tales” to “Changing Channels” to “Mystery Spot”, it’s never disappointing to see Richard Speight Jr. appear with Sam and Dean. When it was revealed that he was actually the archangel Gabriel, that made him more interesting and more pivotal to the mythology. Though he was often messing with Sam and Dean, he was also trying to teach them a message and sometimes protect them.
3. DICK ROMAN
It seems crazy that it wasn’t until season seven that Supernatural introduced the idea of monsters in corporate America. As if the leviathans weren’t powerful enough, their alpha took over the life of tycoon Dick Roman. The monsters used the influence of Roman Enterprises to advance their plan of making humans a completely docile food source.
It wasn’t just that leviathans were more difficult to kill than other creatures, they were also extremely smart. Basically Sam and Dean were fighting way above their weight class. Sadly, Dick even killed Bobby. The leviathans were ahead of the brothers for the entire season. It wasn’t until the season finale that they really had any kind of advantage. However, the boys put together one of their ragtag band of demons and angels with a common enemy and found a way to out smart Dick.
No one has tormented Sam Winchester more than Lucifer. Not Azazel, not Lilith, not Ruby, not even himself. Since before he was born, everything that has gone wrong for Sam has been because of Lucifer. He sent Azazel out to look for special kids, which led to the deal with Mary, which led to her death and Sam being fed demon blood. Later it’s revealed that angels made sure John and Mary fell in love so they would have Sam and Dean, who were meant to be Lucifer and Michael’s vessels.
As if that wasn’t enough, he’s the reason Sam went to Hell, then drove him crazy.
In the world of Supernatural there’s really only one contender for best villain: Crowley. The former king of Hell has tormented, helped and saved the Winchesters through eight seasons. What makes him so captivating is that fans find themselves rooting for him sometimes. Mark A. Sheppard is simultaneously scary, charming and hilarious.
Even when he’s torturing and killing, he’s cracking a joke, but it doesn’t make him any less intimidating. As much as he hated the Winchesters he could never quite bring himself to kill them since they kept things interesting for him. Yes, he was pretty much terrible right up until his death, but when the time came Dean prayed to God to get him back because he couldn’t handle losing one more person. At its core Supernatural is about two brothers hunting monsters, but any fan will tell you there’s definitely something missing without Crowley.
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