Crowley plays a key role on the Supernatural episode "The Devil You Know." This demon is played by Mark Sheppard.

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Supernatural Season 5 Episode 20: "The Devil You Know"
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Supernatural Season 5 Episode 20 Quotes

Sam: What if you guys lead the devil to the edge, and I jump in?
Bobby: Sam...
Sam: It'll be just like when you turned the knife around on yourself. One action, just one leap.
Bobby: Are you idgits trying to kill me? We just got done talking your brother off the ledge, now you're lining up to say yes... This isn't an option, Sam.

Dean: [wearing a surgical mask] Hey, I looked like the King of Pop.
Sam: [Rolls eyes]
Dean: Too soon? Too soon.