Desperate times call for desperate measures. With the apocalypse just around the corner, the demon Crowley, played by Mark Sheppard, makes his return offering the Winchesters his help. Apparently, every demon on earth is after him and Sam and Dean are willing to trust him more than the angels of late.
The episode involves Crowley helping Sam and Dean track down the last two horsemen, Death and Pestilence. While he doesn't know where they are, he knows that another demon named Brady who may able to give them answers. Of course, everything doesn't happen according to plan and the end of the show leaves us with a rather startling proposition, leaving one character's fate in jeopardy.
"The Devil You Know" was one of the worst episodes of the season. Its overall pacing and tone were incredibly uneven and most of the time, it was boring. A good portion of the show was spent talking about how they were going to get the horsemen's rings rather than actually trying to get them. Although the hellhounds make a return in this episode and there is a scene where Dean is getting beat up again, there is no sense of urgency behind it. Near the end of the season, a few invisible hellhounds just don't cut it when there are angels, demons and an ever present apocalypse.
Since his first appearance in the episode "Abandon All Hope", Mark Sheppard has been excellent as Crowley. His character never feels like a knock off of Ruby or Meg but very much his own which is rare in Supernatural. Sheppard is standout whenever he is in a scene because his delivery of dialogue is incredibly cynical while his true motivation for helping the Winchesters is to save his own skin. Even when Brady won't help them, his line "Lovers in league against Satan" is hilarious in delivery. Unfortunately, the demon becoming allies with the Winchesters has been done before in almost the entirety of seasons three and four and is becoming a tired act. Allying themselves with Crowley at this point doesn't seem that desperate when they have done the same with Ruby, it just seems like the show is going through the predictable motions at this point.
The demon Brady, play by Eric Johnson of Smallville and Flash Gordon, seems like a poorly thought out character. While Eric Johnson is excellent as a power suit wearing demon, his involvement with Sam's past had to be a low point in the series as a whole. This plot move is painfully forced and rather than show us a flashback or have the episode start eight years ago when Sam and Brady were in school together, the show just assumes we will believe this artificial connection between the two. I know the show doesn't have the budget of Lost or V, but Brady has never been on the show in any capacity, and considering they also stole a key moment from the YED (Yellow Eyed Demon) and give it to Brady, it was disappointing. It would have been better if Eric Johnson had played a horseman because based on his performance in this episode he would have done a better job than some of those actors.
Whether or not Bobby chooses to make a deal with Crowley will greatly affect the overall tone of Supernatural. The scene was something integral to his character but it was at the end of the episode and only given a few minutes and not given due justice. Jim Beaver has been outstanding as Bobby but this scene could have been longer and let both he and Mark Sheppard show the gravity of dealing with Bobby's soul. Sometimes the show just needs to slow down and not rush something so important rather than just rush to the conclusion.
Besides a few superb performances by guest stars, "The Devil You Know" has brought down the show's momentum. Besides finding out the location of Pestilence and Death nothing was accomplished. If this was a previous season, Sam and Dean would have done research to find Pestilence and Death but now they need help from all sides – making them seem less capable. This episode was an hour long set up for next week when Pestilence and Death appear which makes wonder why there aren't any female horsemen.