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The Devil You Know

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Title The Devil You Know
Series Supernatural
Season 5
Episode 20
Written by Ben Edlund
Directed by Robert Singer
Guests Jim Beaver as Bobby Singer
Mark A. Sheppard as Crowley
Eric Johnson as Brady
Previous episode Hammer of the Gods
Next episode Two Minutes to Midnight
Episode list Season 5

The Devil You Know is the 20th episode of Season 5. It aired on April 29th, 2010.


The demon Crowley tells Sam and Dean he can help them find the remaining Horsemen rings so they can trap Lucifer.

Summary Edit

Dean and Sam encounter Crowley while on the trail of Pestilence. Both brothers are angry at Crowley for giving them the Colt which did not work on Lucifer. Crowley mentions that he's being hunted down by his fellow demons and tells the brothers that he knows where the last two rings can be found. He directs them to Brady, the demon handler for the Four Horsemen of the Apocalypse. However, Crowley will only show the way if Sam does not go with them.

Later, Sam and Bobby have an argument over Sam intending to trick Lucifer back into Hell by letting the Devil possess him. Dean meets Brady, the demon-possessed CEO of a pharmaceutical company, who is under Pestilence's orders. Dean tries to trick Brady with a proposition but the demon does not buy it, intending to just kill Dean. However, Crowley gets the drop on Brady and knocks him unconscious. Dean is warned by Crowley that Sam and Brady have a history; Brady is in fact Sam's classmate from college. The Handler possessed Brady since sophomore year, and deliberately introduced Jessica to Sam and then killed her to put Azazel's plans into motion. Sam is furious and wants to kill Brady but Dean stops him. While Crowley is away, Sam traps Dean in the bathroom as he plans to kill Brady. Brady goads Sam into killing him but Sam manages to calm himself and leave. Crowley returns after killing a nest of demons and making it look as though Brady joined his side.

However, Crowley is tracked down by a hellhound. Crowley escapes, leaving Dean, Sam and Brady in the hideout. While Dean attempts to fight off the hellhound, Crowley returns with his own hound against the other hound. After the four of them escape, Brady gives up the location for Pestilence. Dean then allows Sam to finish Brady off. Later, Crowley appears to Bobby and tells him he will reveal Death's location in exchange for his soul.

Major Characters Edit

Minor CharactersEdit

Featured Supernatural BeingsEdit


Bobby (to Crowley): Well, then get the hell off my property before I blast you so full of rock salt you crap margaritas.
Crowley (to a hellhound): STAY!
Dean: You can control it?
Crowley: Not that one, I brought my own. Mine's bigger. 
Dean: What the hell was that?
Crowley: That was perfect.
Dean: Perfect? He didn't want the rings, he wanted me.
Crowley: Imagine the surprise on your face.
Dean: What?
Crowley: Your ignorance and misinformation, it's completely authentic, you can not fake that... What? It went like clockwork.
Dean: Not for me, you son of a bitch.
Crowley: That's what you get... working with a demon.

Notes Edit

  • Antagonists: Brady and Hellhound
  • Pestilence only appears in a flashback at the beginning of the show and Brady communicates with him in a bowl of blood similar to the one the demon that possessed Meg Masters used to communicate with Azazel.
  • The episode title is the shortened form of the full idiom, 'better the devil you know than the devil you don't'. It means that it is often better to deal with someone or something you are familiar with and know, even if they are not ideal, than take a risk with an unknown person or thing. In this case, Crowley is the devil that Sam and Dean know.
  • In the very beginning of the episode (after the recap), a poster for Herpexia, the medicine for genital herpes that the Winchesters are forced to do a commercial for in Changing Channels can be seen, hinting that Niveus Pharmaceuticals is its creator.

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