These 7 villains nearly got the Winchester brothers in Supernatural

Supernatural is more than a story of monsters, angels, and demons, it's a legend of two brothers who were constantly tested to the breaking point. Dean and Sam Winchester endured everything from demon possessions to godly battles, and despite it all, they always managed to make it out alive. But that survival wasn't easy.

Over the course of fifteen seasons, there were times when it almost appeared as though the end was truly in sight, when even their adamantine will and unbreakable partnership would be insufficient. The villains of Supernatural were not your ordinary run-of-the-mill baddies: they were cosmic entities, ancient entities, and warped masterminds that played long games and striked where it hurt the most.

Some almost murdered the Winchesters, while others used them to make them turn against one another. Whether it was Lucifer messing with Sam's head, Amara seeking to destroy God's creation, or Rowena's lethal application of magic, these foes weren't just frightening, they were clever, and relentless.

Here are seven of the most dangerous villains on this list who came close to killing the Winchester brothers once and for all. They are not just villains. They are nightmares that lingered long after the credits had stopped rolling.

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Villains who nearly got the Winchester brothers in Supernatural

1. Lucifer (Season 5)

Lucifer, the Devil himself, was one of the most dangerous enemies the Winchesters encountered. His manipulative skills almost killed the brothers in Supernatural's fifth season. Lucifer's scheme to ignite the Apocalypse came close to completion as he took over Sam, driving the brothers to the verge of annihilation. His clever mind and destructive abilities made him a major threat, but even in their darkest hour, Dean and Sam managed to foil his plans. Lucifer's multi-faceted personality as both villain and victim gave him added depth as a character, making his losses and moments of triumph all the more memorable.

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2. Crowley (Seasons 5–12)

The King of Hell Crowley was a demon with a deformed sense of charm, regularly teetering on the verge of being friend or foe. Since his first appearance in season 5, Crowley had an ability to bend situations to serve him, very nearly killing off the Winchesters on several occasions. As his motivations developed throughout the course of the show, his singular drive for power remained consistent. His alliance with the Winchesters, though short-lived, brought added depth to his character, but his plots such as trying to side with Leviathans almost destroyed what they had.

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3. The Leviathans (Season 7)

The Leviathans, old and all but invulnerable, were a huge problem for the Winchesters in Season 7. Their boss, Dick Roman, possessed the wit to use the world's corporations to his own ends, turning them into the kind of strong monsters that could kill without impunity. These beings were virtually unbeatable, able to heal from almost any wound and destroy their foes with ease. Their violent conquest of Earth threatened humanity with a virtual cataclysm, compelling Sam and Dean to get creative in order to vanquish them, and resulting in a surprising finale with the assistance of Castiel.

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4. The Yellow-Eyed Demon (Azazel) (Season 1-2)

Azazel, the Yellow-Eyed Demon, was the brains behind the Winchester family's ruined past and the bringer of numerous horrific events. His function as the series' initial antagonist was crucial causing the deaths of Mary and Jessica in tragic circumstances. During Season 1, Azazel manipulated events, forcing the brothers to fight demons and other supernatural beings, almost shattering them at every turn. His final scheme was to create a portal to Hell using Sam as a vessel to free Lucifer, and though he was ultimately defeated at the end of season 2 his impact lasted the duration of the show.

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5. Metatron (Seasons 8–10)

Metatron, self-styled "Scribe of God," was a manipulative and sinister character who came close to destroying the entire heavenly framework. During seasons 8 and 9, Metatron led the Winchesters to think he was their friend while planning in secret to banish angels from Heaven, causing havoc along the way. His manipulation of the Angels and his forcing the brothers into an uneasy alliance with him made him one of their most vexing enemies. Ultimately, Metatron's ambition almost destroyed mankind, as his machinations were poised to eliminate the last Heaven-bound angels.

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6. Rowena MacLeod (Seasons 10–15)

Rowena MacLeod, a powerful and manipulative witch, was one of the most unpredictable foes the Winchesters ever encountered. At first, she was an adversary who manipulated both Sam and Dean, but later, she emerged as a major character in the fight against dark forces. Her mastery of black magic, coupled with her ruthless drive, made her a force to be reckoned with. Rowena's familiarity with ancient spells and the Book of the Damned was a virtually lethal resource for the Winchesters, but her multifaceted motivations and maternal love kept her volatile and constantly testing.

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7. Amara (The Darkness) (Seasons 10–11, 15)

Amara, also referred to as The Darkness, was possibly the most overwhelming presence the Winchesters were ever able to encounter. Being God's sister and an ancient power of destruction, she delivered cosmic destruction the brothers were completely unequipped to handle. Her presence upset the order of nature bringing the dead back to life, unleashing the plagues, and promising to unmake creation itself. What made her even more deadly was her complicated emotional relationship with Dean, which blurred the distinction between admirer and enemy. Although her ultimate reconciliation with God averted destruction, Amara's unbridled power and volatile nature brought the Winchesters appallingly close to complete defeat.