Crowley is such a complex character, I am not normal about him.
Like, his whole thesis as a character is this idea that what is Good and what is right and what is nice and what is kind are all very different things. Crowley isn’t Good or nice, but he is righteous and kind.
So it always seemed a bit strange to me how unbothered Crowley is with being a demon. Like, sure, we’ve got the whole “go as far as you can go” with Hell conversation, but Crowley never seems conflicted or remorseful about spreading Evil or condemning souls to Hell. He’s not disgusted or off-put by them. He’s amiable and casual with Beelzebub, he answers Shax’s questions, even Hastur and Ligur don’t bother him until they make it his problem. Generally, he seems to have an overall decent relationship with Hell and it’s denizens.
The angst we do see come from his is all about the Fall and that he doesn’t understand what he did wrong. He feels betrayed by an unjust punishment and he doesn’t understand why it happened. But he never angsts about his new nature as a demon. In fact, I’d go as far as to say he actively likes being a demon.
So it took me a bit to figure out how all that fit together, and I think I cracked it:
Crowley doesn’t think that Evil is bad.
See, if Good isn’t necessarily good, then it stands to reason that Evil isn’t necessarily bad. I believe he even says at one point they are just names for different sides. I think Crowley sees Evil as a way of stress-testing humanity. When he pleads with God he says “you’re testing them, you said you would test them, but you shouldn’t test them to destruction”. It’s not the testing that bothers him, it’s the destruction. With Job, Crowley doesn’t hesitate to destroy the barn and the house, he doesn’t balk that it’s all happening for a bet, but he won’t destroy the blameless goats and blameless kids. He pokes at Job’s insecurities but Job is steadfast, passing God’s test. But Crowley does step in when Cetis is about to spurn God because of the loss of their children, because at that point the test is unfair. And with the paintball incident, he turned the paintball guns into real guns, and the humans know they are real guns. Crowley doesn’t make them shoot- they want to shoot each other. They have no reason to expect miraculous escapes and fully intended to kill each other. They failed the test, but Crowley won’t let them be destroyed for failing, either. And they get punished for failing by getting arrested.
And I think this comes through in the type of evil Crowley spreads- petty irritants, mostly. He doesn’t make anyone do anything they don’t want to go, he just gives them a nudge. And if they fail, they put a light tarnish on their soul. But here’s the thing: tarnish actually comes off pretty easy if you bother to try.