Larger-than-life, witty, and fascinating villains were one of the things that fans of the cult fantasy Supernatural couldn't get enough of. In fact, the show had a range of supervillains who kept the heroic Winchester brothers on their toes.
However, the big baddies alone wouldn't be able to sustain the show had it not been for a variety of other, low-key, but often dangerous antagonists that the brothers had to face and fight. Whether humans, angels, or humans and angels possessed by other angels and archangels, there was no dearth of challenges that the brothers had to rise to, beyond the typical freak-of-the-week monsters.
10 Bela Talbot
Bela wasn't a villain per se as much as she was a troublemaker. She turned up as suddenly as she left but within the short span of time that her path crossed the boys', she brought them a world of trouble, including stealing a staggering 46,000 dollars, that was probably more money than Sam and Dean had or were ever to see in their lives.
Bela also stole the coveted Colt from the brothers, the gun that was the only one of its kind and could kill any entity however immune to other weapons. Never particularly scrupulous, Bela was a slippery eel, but she certainly wasn't as horrifying as some of the people or creatures that Sam and Dean go on to meet. Her death, presumably by hellhounds, seemed a tad harsh and the boys seemed to forget about her pretty soon.
9 Anna Milton
The fallen angel Anna seemed like a potential ally for the brothers and Castiel at first, and even had a steamy night with Dean at the back of the Impala, one of the many emotional Supernatural moments the Impala had been through. She was an angel who had revolted against the requirements of Heaven and thus seemed like one of the good guys, capable of thinking of her own.
However, she soon became antagonistic as she decided to go back in time and kill Mary and John Winchester so that Sam and Dean would never be born, the first of the 66 seals that needed to be broken to unleash Lucifer upon the earth would remain intact, and most importantly, Lucifer would not have his true vessel. She was then killed off by the archangel Michael possessing John who wanted to save his wife and although it meant that the apocalypse couldn't be stopped, Anna's death was good riddance.
8 Gadreel
Not an out-and-out villain, Gadreel was one of the main characters in season 9, and a secondary antagonist of sorts after Metatron, the scribe of God.
Gadreel had taken refuge in Sam's body after most of the angels were ejected from Heaven. Having convinced Dean that that was the only way to keep Sam alive, he ended up becoming the scheming Metatron's right-hand man. While he did seem ambivalent at first, fans went thoroughly against him when Gadreel, possessing Sam, murdered young Kevin Tran in cold blood following Metatron's instructions, and Dean could do nothing about it.
7 Duma
An angel who at first seemed desperate to save a chaotic Heaven, Duma gradually turned antagonistic as she allowed Lucifer to rule over Heaven in return for his help in creating more angels.
She also held sway over Heaven briefly herself, creating a reign of terror which made Heaven a brutal final destination for humans. She also manipulated Jack so that she could have his tremendous power at her disposal, and eventually became a vessel for the Shadow, the entity ruling the Empty, one of the main locations/sets on Supernatural, since time immemorial. Duma was yet another loose end that needed tying up which Cas finally did.x
6 Billie
Billie the reaper became Death after the former Death was killed with his own scythe by Dean Winchester. Initially appearing to be an ally who wanted to save the world and destroy God just as the Winchesters did, Billie turned out to be a villain too towards the end of season 15.
Billie's endgame was ambiguous, for the most part, although it seemed as though she was on the brothers' side and wanted to get rid of God. To that end, she had even had Jack resurrected and told him how he could improve his strength which he would need to preserve to kill God. Yet, at the end, it was revealed that Billie had been manipulating the brothers and Jack all along. She wanted to kill God not to save the world but to take over the universe herself.
5 Toni Bevell
Although not exactly low profile, Lady Toni Bevell became a temporary villain in season 12 as the merciless killer on the British Men of Letters' payroll.
Bevell was shown to be a terminator of sorts, with very little morality or scruples to anchor her, and willing to go to any length to follow the instructions coming from upstairs. She abducted Sam Winchester and tortured him inhumanly, all to please the high command, And unlike Ketch who at least had a compelling personality, Bevell's character was simply irritating. This was one villain fans hated unlike some of the other Supernatural villains whom they loved.
4 Uriel
One of the earliest angels the brothers met, Uriel deceived everyone (including Castiel) when it was revealed that he was actually working to bring about the apocalypse, rather than helping to stop it.
As the Devil's mole in Heaven, Uriel was one of the angels who had turned against God, sick of his absence and tired of following instructions from someone who never really showed up. He was probably the one who proved to Sam and Dean that angels, contrary to popular perception, weren't necessarily the good guys. Uriel was still just a pawn since more important angels like Zachariah soon joined the party and made life a living hell for Sam and Dean. But he was the first of the villainous angels the brothers encountered.
3 Castiel
Castiel makes this list since he nearly went dark side more than once. Season 6 saw Cas going rogue, killing hundreds of his fellow angels, to say nothing of humans he massacred. The idea of becoming God possessed him to the extent that he lost any ounce of humanity he might have picked up from spending time around humans like Sam and Dean.
Later too, Cas agreed to let Lucifer in so that they could beat the Darkness. However, Lucifer had his own plans and the Cas shaped Lucifer soon took over Hell where he kept Crowley under captivity, killed Rowena and basically raised hell. Castiel himself might have been the best of entities, but he made some choices that didn't go so well, especially for him.
2 Soulless Sam
One of the villains in the course of the series that fans might have forgotten but who was definitely a key antagonist at the time was Soulless Sam. Sam Winchester returned in season 6 from Lucifer's Cage in Hell where he had been broken and battered to the point that when he returned, his soul had been left behind.
The havoc that the Soulless Sam wreaked became a major plot point in the sixth season as Sam lost his connection with the softer human emotions and didn't care if he had to kill a few perfectly innocent humans here and there. He even set a vampire on his own brother knowing that the latter ran the risk of getting turned, and indeed he did! Soulless Sam might have been pretty low-key in the context of the entire series but he was quite terrifying for a period of time.
1 John Winchester
Of course, John Winchester was a good man who had met with a terrible tragedy when his wife died so shockingly, leaving him with two young kids, one of them an infant. It was also he who taught the boys everything they knew about hunting.
However, there is a reason Supernatural fans consider Bobby a better father to the brothers than John Winchester. it was John's obsession with finding the demon who had killed his wife that led Sam and Dean down this path from where there was no turning back, that took away their childhood. And although they did save the world multiple times, and certain events had been set in motion that would have affected them anyway, the brothers only had their father to thank for a lot of the sacrifices they had had to make.
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