, Sam and Dean Winchester have faced off against all kinds of monsters. From angels to Wendigos, the brothers have dispatched most evildoers with relative ease. But a certain class of villain has proven much harder to handle. This elite group of bad guys have been able to outsmart, outmatch, and sometimes even manage to escape certain death. Here are six of the hardest to kill villains
has seen two incarnations of the Archangel Michael. The first was locked away in Lucifer’s cage fairly easily and did little damage. However, Michael, from the alternate Apocalypse World, has proven to be far more troublesome. He wreaked havoc on his world, decimating both Lucifer and Gabriel.
As the oldest Archangel, Michael is extremely powerful. His savagery knows no bounds and he’s very methodical in his actions. He’s a proven leader and has no problem getting soldiers to join his army. He will make deals when he has to and takes pleasure in committing acts of violence. Michael is deceptive when it suits him and is even more powerful now that he is utilizing his true vessel, Dean.
Crowley is a crossroad demon-turned-King of Hell who has always managed to make himself both friend and foe. Since his first appearance in Season 5, he figured out how to escape the brothers’ wrath. Crowley proves his usefulness to the Winchesters by helping them dispatch other villains, even coming to their rescue at times. Then he flips a switch and shows why he’s a villain by tracking down and killing survivors who were once saved by the Winchesters.
The King of Hell has been so hard to dispatch because he’s adept at reading people and situations, then acts accordingly. Crowley has shown he’s willing to do whatever is necessary to survive and further his agenda. He once escaped death by using a rat as his vessel and scurrying away to safety. However Crowley seems to have a change of heart, and in true hero fashion, sacrificed himself in Season 12 to save Sam and Dean.
Rowena is another villain who has managed to escape death several times. She is a powerful witch who seems to take a page out her son, Crowley’s book. She has saved the Winchesters numerous times using her powerful spells, all while going after what she wants. She does this to not only regain her full power but also to amass even more. Rowena has managed to survive for so long because she plans ahead.
She placed a Resurrection Seal within her body to ensure her life after her demise. She has also proven an invaluable, albeit reluctant, ally to the Winchesters, which makes them less likely to kill her. Rowena’s manipulations and powerful spells have seen her through many tough spots which is why she has outlasted numerous attempts on her life and has fared far better than most villains.
Metatron was a lowly scribe angel who ended up being more than a nuisance to the Winchesters. He used his intelligence and unassuming appearance to lull both the Winchesters and the angels into believing he wasn’t a threat. However, Metatron proved to be malicious, cruel, and devious in all his encounters with the brothers. He even killed Dean, causing his resurrection as a demon.
The angel was so hard to kill because he had a way of making everyone believe whatever he wanted them too. In Season 8, Metatron tricked the brothers into performing three trials that were supposed to seal up hell, but instead, it emptied Heaven of all the Angels. He captured Castiel, stole his grace and killed several of his fellow Angels. All his scheming and vengeful plots to take over Heaven and become the new God ended up catching up with him when he unwittingly exposed his true motivations to his followers, allowing for his capture.
Lucifer is the second most powerful archangel. He tricks, torments, deceives, and tortures without any remorse. Lucifer knows the depths of his power and uses everything at his disposal to get his way. This fallen archangel has been so hard to kill because he is ruthless and thrives on carnage.
But like Crowley and Rowena, he manipulates a situation and then goes in for the kill. Even though Lucifer’s son, Jack, is more powerful, Lucifer was still able to catch Jack off guard to steal some of his grace. The gang had been trying to kill Lucifer since Season 5, but he has always managed to find a way to escape even their best efforts. Lucifer finally met his end in Season 13, but it took Dean finally becoming Michael’s vessel to accomplish the task.
universe. She’s older than both God and Death and after being locked away for thousands of years, she was determined to destroy God. Her rage and jealousy along with her abilities make The Darkness especially hard to kill. It took the combined efforts of God, Lucifer, the witches, angels, and demons to even damage Amara. Yet, even after all that, she was able to recover and fatally wound God.
For Amara, taking out all of creation is no empty threat. She destroyed everything God created before mankind. Out of jealousy, she would have also eliminated his newest and dearest creation, so God formed the Archangels to help him seal her away because if she were killed, that would throw the entire universe out of balance. Luckily for the
team, Dean talked her down by getting her to understand that families sometimes fight, but they still love each other. This led her to rethink her plans for destroying everything and reconcile with her brother, God.
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