Sam and Dean Winchester have pretty much fought every creature we regular humans can find in mythology, folklore, and various religious texts. They've gone from being called their father’s bitches in the show's early seasons to now become pretty much untouchable. However, sometimes they don’t seem to use their thinking caps, and the big bads can be found right under their noses!
Sam and Dean have faced many formidable villains throughout Supernatural's run, but here are the best of the best.
When Ruby swooped in with her ancient demon-killing knife to save Sam’s ass back in Season 3, a lot of us were pretty convinced that no demon would fight with their own kind without an ulterior motive. But we forgot all about this when she repeatedly saved the Winchester boys, even though we still couldn’t quite shake off the feeling that there’s something about her that isn’t to be trusted.
Ultimately, Dean and Bobby were right about Ruby – unlike Sam, who had become twisted and manipulated by drinking her blood. She may not have been a ‘big bad’, just a secondary villain, but her ingenious plan to lead Sam into breaking the final seal earns her a place on this list.
When we got introduced to Zachariah back in Season 4, we initially thought he'd be a good guy – even though there was something in his eyes that raised a red flag. Still, we gave him the benefit of the doubt because he didn’t outright show contempt against humanity, unlike Uriel. But, everything changed when we found out – like most of the angels - that he wanted the big brawl of Lucy and Mike to happen.
In big ol’ Zach’s words, Lucifer may be strong, but he was petty. So, I’m sure that when Dean called Zachariah "a dick" and stayed true to his word by sticking a knife in his face, we all collectively cheered.
Eve was a force to be reckoned with. As the mother of all monsters, she was thoroughly pissed off when she found out her relatives were being horribly tortured or killed so that psychopaths could find the entrance to the hell-adjacent Purgatory. She was extremely powerful, hard to track, and hell-bent on getting back at the King of Hell. To do this, she decided to try a little experimentation and left a lot of beta-tested Jefferson Starships in her wake.
Eve wasn't really the worst among the roster of baddies the Winchesters encountered, but the 'Khan' she created possessed Dean, which prompted the latter to kill his cousin, and the same slug-like critter caused the death of Rufus Turner and Samuel Campbell (not that he was such a good grandpa, but still). She wasn’t a villain whose plans were originally to take over the world, and her intentions to turn humanity into monsters was so the d-bag C-squared would have no souls to harvest. She ultimately went back to Purgatory when she ingested Dean’s blood laced with phoenix ashes.
The famed ‘yellow eyes’, one of the princes of hell, was the cause of all the boys’ troubles since the beginning. Lucifer was uncomfortably cooped up in his cage, and even when all the other demons turned their backs on their creator’s plans, Azazel remained loyal to the cause.
So, Azazel began scouting for candidates for his demon blood-powered special children that would one day fulfill the destiny of breaking the final seal and freeing Lucifer from his cage. However, because this big bad only thought of the Winchester boys as harmless kids blindly following the orders of their father, the big league demon died by underestimating the boys.
Lilith was the new face in town, and was the key to free Lucy from his cage. Apparently, she stepped in to become the new leader of hell once Sam failed to take the mantle. Lilith enjoyed power too much, became the new queen, and held the one year (just one friggin’ year!) contract of Dean Winchester and other miserable souls desperate enough to kiss a deal with a crossroads demon.
She was also the only one who knew of Ruby’s loyalty, and together they planned to push Sam to the edge and fulfill his destiny. Granted, all of the grief she put Sam and Dean through was a part of their grand plan, but she didn’t have to sic a hellhound on an already helpless Dean while making Sam watch – that’s a level of petty even Zachariah would be proud of.
6. Megalomaniac Castiel
Castiel has grown so much as a character because of the changes he’s been through. He was a rebellious angel who was resurrected and became a Seraph. When he become human, he truly understood the beauty of life for the first time.
But, there was a time when Castiel was one of the worst creatures the Winchester boys have ever encountered; t'was when he absorbed all the of souls from the untapped power well, Purgatory. The turning point of Castiel truly becoming the ultimate villain of Season 6 was the moment he killed his old friend, Balthazar. Despite my love for Castiel, I wanted to stab him with an angel blade when he did that.
Castiel’s strength and weakness was that he had too much heart; he cared and meddled too much, and often felt he was above the others. This was proven when he did horrible things just to win the civil war in heaven. He set an example for other angels when he questioned authority and didn’t blindly follow orders, but when Balthazar did just that to Castiel, the latter killed the poor bloke!
First, his intentions were in the right place, but when the god complex took hold, he just couldn’t pull his head from the clouds until it was too late.
5. Leviathan Dick Roman
There was one reason why Crowley, the King of Hell, wanted to be partners with the colossal Dick: They were both visionaries, always looking towards the road ahead. But Dick didn’t want to do business with Crowley because as ancient predators – older than angels, demons, and other monsters - Dick knows that leviathans are above all other beings. That made them pretty much impossible to kill, and their only known weaknesses were borax and decapitation, which would render them helpless for a while, but not completely dead. Life was unnecessarily harder for Sam and Dean while Dick and his leviathan minions were out and about.
In order to have further control over the food chain, Dick wanted to find a cure for cancer as well as make high-fructose corn syrup more addictive so that he’d have the perfect cattle and no leviathan would ever go hungry again. Bobby lost his life because of this, but luckily the Winchesters snagged the word of God and had a prophet on their side, which allowed them to decode the manual on leviathans and send Dick back to Purgatory in an ugly explosion of black ooze.
Unlike Azazel, Abaddon didn’t underestimate the Winchesters. She learned her lesson when the time-traveling Henry Winchester lodged a devil’s trap bullet in her throat. But because our favorite protagonists have an affinity of telling monsters exactly what they intend to do to them, Abaddon was able to break free. Granted, the boys didn’t have quite the rockstar reputation they have now, she was still wise enough to utilize the future’s tools (like Kevlar) to her advantage.
This time-traveling devil didn't only put hell on earth for the younger Winchester boys, but also for old Henry Winchester and Crowley. No one can negotiate with Abaddon, and it doesn't help that she can't be killed by conventional means. But like Crowley said, one cannot rule using chaos alone, and her plans to oust Crowley backfired because the he allied himself, once again, with the Winchesters.
If Crowley really wanted to, the punk-ass crossroads demon turned King of Hell could very well kill Sam and Dean. He had an on-off relationship with those two, negotiating with them so that he’d keep his position as king. However, he wasn’t above sending hurdles to the boys whenever he saw fit (and sometimes, maybe just for kicks).
Of course, Crowley was a weaker demon compared to those he previously served, but his intelligent decision not to underestimate the denim-wrapped nightmares made him a formidable foe. Like Meg (whom this bastard killed), it was great to see Crowley become one of those demons who found a genuine cause and stuck to it. Long live the king!
2. The Darkness
The ‘can’t or won’t’ question the Winchesters love to ask whenever someone wouldn’t help them applies to God’s sister. Hell hath no fury than a woman scorned, and Amara was rightfully pissed off after being locked up for a million years by her lil bro. When Amara was released from her prison, she was hungry for souls and was out to destroy everything God created just to settle a score.
In another circumstance, the boys would do everything to gank her, but one must not kill her for the sole reason that worse can happen if Michael and Lucifer had their pissing contest.
We’d never know light if there was no darkness, and reality would cease to exist if she were to die. It was necessary for Amara and Chuck to talk things out as she wasn’t a villain that the Winchesters had to take down on their own.
This list wouldn't be complete without Chuck's most trusted lieutenant. He shouldn't be blamed for every bad thing that has ever happened in the show (mostly to the Winchesters) because the Mark (which turned out to be a curse) corrupted him, leading to his banishment from heaven. We can sympathize with him to some extent - but then again, he still had a hand in nearly all the misfortunes that befell the boys and the corruption of the human race; for that reason, he is number one in this list even though the Darkness is a lot stronger than he'll ever be.
Lucifer had daddy issues and was spoiled. Gabriel was right in saying that his inability to forgive and acknowledge his own mistakes makes humans better creatures than them. It's also possible that Lucy could become the main villain in Season 13 because he isn't dead, just trapped in an alternate reality with Mary Winchester.
Since God left, the angels wanted nothing more than to bring forth the end of days with the eldest archangel as their champion. Michael was trapped in the cage for many years now (since Season 5), possessing the body of Adam Mulligan, the half-brother of Sam and Dean. Could it be that he's been plotting his revenge and patiently waiting for the day he can be freed from his cage? The show's executive producer Andrew Dabb said in a SDCC interview that Jack (Lucifer's spawn) won't be the biggest threat, but rather “it’s an old — let’s call him friend — who we have not seen for many years.”
Michael certainly fits the criteria, but we shall wait and see. There are many potential bad guys to return, but Michael seems the most plausible. After all, he was ready for the fight of the millennium, but his feathers were ruffled and thrown into the cage just because of two mortal men.
In the Season 12 finale, Jack was born and we saw his golden eyes creepily glinting. Jack is the only Nephilim sired by an archangel (the fallen one, too) and it's too early to say that he'll be evil. After all, he's a newborn and since Dagon was eliminated, we can hope that the Winchester boys can instill goodness and kindness in this kid to ensure that he won't grow up like his father.
But as we know, Supernatural is always up to mess with our feelings, and just when we thought things will somehow get better, they won't!
At the end of the day, the upper hand the boys have over the big bads is that they aren't too proud to admit to whatever issues they have. Meanwhile, the show's villains tend to have their heads too far up in the clouds. Borrowing the words of Zachariah, Sam and Dean are "psychotically, irrationally, erotically codependent on each other", and they both have this stupid, suicidal self-sacrificing habit for each other. However, as long as they're together, they'll figure something out – just like they always do.
#Supernatural will be back in our screens, October 12, 2017, on The CW.
Who are your favorite Supernatural villains? Let us know in the comments!