‘You do want to conspire, don’t you?’
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Not only does Crowley not underestimate the Winchesters, he also knows that when their interests line up against a common enemy, it’s best to team up. Where lesser demons would have been squashed by a rogue angel or leviathan, Crowley is still kicking because of his frequent uneasy alliances with the brothers. Always looking out for number one, Crowley is also always ready to backstab Sam and Dean the moment the opportunity arises.
‘This isn’t Wall Street. This is Hell! We have a little something called integrity!’
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Crowley takes pride in his work. He moved up from sales to become the King of Hell in the power vacuum after Lucifer was locked back up, and he’s not content to rest on his laurels. He wanted to weaponize the souls of Purgatory, he survived a power play against a Knight of Hell, and he took the opportunity to make Dean dependent on him as the effects of the Mark steadily worsened. He keeps the deals he makes and expects his underlings to do the same.
‘I deserve to be loved! I just want to be loved.’
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The Winchesters made Crowley the target of the final demon trial; Sam had to inject him with his blood in order to cure him. As the curing process went on, Crowley began presenting increasingly human emotions, much to Sam’s surprise. Though Sam didn’t end up completing the trial, Crowley spent much of season 9 gripped with addiction to human blood and faced with remnants of human emotions, giving everyone, including Crowley himself, a completely new view of the demon.
‘You’re good. But I’m Crowley.’
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With all of Crowley’s snark and his frequent alliances with the Winchesters, it can be easy to forget that he’s incredibly dangerous. Crowley didn’t become the King of Hell for nothing, and he knows it. He’s not just manipulative; he’s also deadly.
‘Let’s go take a howl at that moon.’
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Crowley’s monologue over Dean’s corpse in the season 9 finale was surprisingly earnest. He helped Dean take on the Mark of Cain and continued to shape him as the Mark increasingly affected the older Winchester. But he seemed regretful of Dean’s death, saying that he’d never lied to Dean — only refrained from mentioning that when Cain tried to kill himself, the Mark wouldn’t let him go. We’ll be interested to see what kind of interactions Crowley and demon Dean have in season 10.
Honorable mention
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