Demons are prevalent from the very beginning of Supernatural. Although Lucifer is considered the main antagonist by most fans, he’s an archangel. Crowley becomes “King of Hell” and is the enemy at times, but also an ally. In season 1, Azazel is the demon that John Winchester is hunting, responsible for all the strife the Winchester family has gone through.
The demons started out as pawns under the control of some mysterious entities, with Azazel being the plague of the Winchester Family's existence. As the series went on, new classes of demons emerged, as did more sinister plans. Every new piece of information showed the demons getting worse and worse.
10 Demons Started The Winchester’s Dark Legacy
The alternate Apocalypse world showed fans what the world would be like if the Winchester’s had never been born. Mary Campbell, before she married John Winchester, was a hunter and the Winchester legacy was supposed to be as Men of Letters.
Because of demons, Knights of Hell, and all of their plots and plans, Sam and Dean became hunters with their father due to Mary’s death at the hands of Azazel. Sam got back into the game because of Jess' death at the hands of another demon, mimicked to look like Mary’s death. Fans saw how demons began the Winchester's dark legacy, but what they didn't know in that first season was just how bad it was going to get.
9 Tragic Winchester Demon Deal
Crossroads demons make deals with humans that give them a wish in exchange for their souls. The standard deal is to give the person selling their soul 10 years before they are mauled by hellhounds and dragged to the pit to be tortured for all eternity.
At the end of season 1, John Winchester makes a deal to save Dean and he gets barely a few minutes before he drops dead right on the floor of the hospital. At the end of season 2, Dean makes a deal to save Sam’s life and is given a year before he’s mauled and sent to the pit. This was all part of Azazel's grand plan. The deals were unfair because of what he needed from the Winchesters.
8 Escape From Hell
Part of Azazel’s plan relies on opening up one of the gates of Hell so that Lilith can escape and begin breaking the seals that would open Lucifer’s cage. He succeeds and Lilith isn’t the only demon that escapes. It is estimated that hundreds or possibly thousands of demons escaped in the minutes that the gate was open.
This was the beginning of several new classes of demons to be found out. The Winchesters killed Azazel at this time, but they had no idea that their demon problems were about to get worse.
7 Deceptive Allies
In Season 4 and Season 5, the apocalypse arc leads up to Lucifer and Michael in an epic battle that would have decimated a large portion of the world and the human population on Earth. While Lilith was breaking seals, the demon Ruby manipulated Sam into believing they were allies so that she could get him ready to kill Lilith, which was actually the last seal that would release Lucifer.
Crowley gives Sam and Dean The Colt, a gun that could kill all but five beings in the world. He wants them to kill Lucifer and plays at being an ally. In the end, he becomes King of the Crossroads and then King of Hell. Ruby and Crowley are among the more powerful demons that Sam and Dean run into. At this time, fans see that demons were once human, something that made them so much worse than simple soulless monsters.
6 Crowley’s Play For Purgatory
Crowley gets the idea in season 6 that he needs more “real estate” than just Hell and schemes to take over purgatory. This involves manipulating a resurrected Samuel Campbell (Mary’s father) into hunting down “Alpha” monsters and finding out where they came from. The torture of Alphas brings the wrath of the mother of all monsters, Eve.
In his ploy to open the doors of purgatory, Crowley gets Castiel involved, who ends up taking in the millions of souls that Crowley wanted for himself. King of Hell wasn't enough for him. He wanted more and, because of his myopic vision, he pitted family against each other, one bond that fans hold sacrosanct in this show.
5 Chased, Captured, And Tortured Prophets
Crowley set his demons to find Kevin, the Prophet, so that he could have a personal translator for the Word of God stone tablets. As always, he wanted power, above all. When Kevin didn’t want to cooperate, he tortured the angel Samandriel to find the names of other prophets, capture them, and use them as leverage when torturing Kevin.
It was shown earlier that the angels held prophets in high esteem. They were supposed to be protected. Their souls were sacred. Crowley kidnapped them anyway and made his demons do their worst so Crowley could get to Kevin.
4 Knights Of Hell
The Season 8 episode “As Time Goes By” revealed that John's father Henry went back in time to get help from John, who was dead, in defeating Abbadon the Knight of Hell. In the 1950s, she decimated the Men of Letters after finding out that they were trying to turn demons human.
The Knights of Hell were a new class of demon and Abbadon turned out to be the first one that couldn't be killed with the Demon Knife the Winchesters got from Ruby. All the knowledge of demons they had was useless against her. Fans saw a new side of the demons, but it got even worse from there.
3 Demonic Origins Revealed
In order to defeat Abbadon, the Winchesters need The First Blade and for that, they have to find Cain. He reveals the history of the Knights of Hell, how he trained them, and how the Mark of Cain allowed him to wield the first blade. After Abbadon possessed the love of Cain’s life, resulting in her death, Cain killed all the other Knights of Hell.
This part of the story gave Sam and Dean a way to kill Abbadon, The First Blade. But to wield it, Dean had to take on the Mark of Cain. Cain was a demon that was corrupted by the mark, something he failed to tell the Winchesters, and when Dean was killed, the mark wouldn't let him die. He became a demon himself.
2 They Lost Michael
After Crowley sacrifices himself to close the rift to Apocalypse world, there is no ruler left in Hell until Rowena makes a similar sacrifice and ends up the new Queen. Shortly before that, Chuck/God told Sam and Dean “Welcome to the end” and snapped his fingers. Rowena tells them that this opened every door in Hell, including Lucifer’s cage, where Michael had still been trapped.
During the power vacuum between Crowley’s death and Rowena’s takeover, Michael was lost. When they needed him most, the demons had no idea where he was. When the Winchesters thought they finally had a real ally in Rowena, she and her demons lost the one person they needed the most at that time.
1 Princes Of Hell
Before the Mark passed to Cain and Lucifer handpicked the Knights of Hell, the Princes of Hell were created. They were the first generation of demons after Lilith was created and possessing powers nearly parallel to Lucifer’s, but not as strong. It is revealed that Azazel was a Prince of Hell. Next was also Ramiel, who came after Cain but was killed. Dagon protected Jack’s mother Kelly Kline while she was pregnant, hoping for praise from Lucifer, but was killed by Castiel.
Asmodeus captured a presumed dead Gabriel and injected himself with Archangel grace to gain more power. He was later killed by Gabriel. All of them in their quest for power believed themselves to be the rightful rulers of Hell. Each Prince caused mayhem and strife in the lives of the Winchesters and those around them. They were the highest class of demons and the absolute worst.
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