30 best Supernatural episodes ever ranked

Supernatural "Pilot" Image # SN100-6733 Pictured (l-r): Jared Padelecki as Sam, Jensen Ackles as Dean Photo Credit: © The WB / Justin Lubin
Supernatural "Pilot" Image # SN100-6733 Pictured (l-r): Jared Padelecki as Sam, Jensen Ackles as Dean Photo Credit: © The WB / Justin Lubin /
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“On The Head of a Pin” – Christoper Heyerdahl as Alastair and Misha Collins as Castiel in SUPERNATURAL on The CW.Photo: Sergei Bachlakov/The CW©2009 The CW Network, LLC. All Rights Reserved.
“On The Head of a Pin” – Christoper Heyerdahl as Alastair and Misha Collins as Castiel in SUPERNATURAL on The CW.Photo: Sergei Bachlakov/The CW©2009 The CW Network, LLC. All Rights Reserved. /

6. On The Head of a Pin

When it comes to emotional episodes, Supernatural Season 4, Episode 16 is the one to watch. Let me start this with saying Christopher Heyerdahl is one of my all-time favorite guest stars on the series. And I definitely love him even more in Van Helsing. It’s not easy for a second demon vessel to stand out and be better than the first, but Heyerdahl nailed Alastair.

“In the Head of a Pin” was more than just a good episode for him, though. Everything gelled beautifully. We got to see more of what Dean went through in Hell and the monster he was starting to become. This gave us more of an understanding of why he hated everything about himself throughout this season.

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We saw the soldier that Castiel was. While he cared for Dean, he needed to get the job done. This was long before Castiel really understood what it was like to be human; long before he viewed the Winchesters as his family. That shows throughout the episode.

Then there’s Sam’s storyline, as he begs Ruby for her demon blood. He needs to get stronger to save his brother and protect the world. We get this development of the addiction storyline and the hold that Ruby has on him.

Finally, it’s all about the end. After everything, Dean completely breaks down. That scene in the hospital as he tells Castiel to find someone else is heartbreak. Jensen’s voice cracks, filled with the emotion we eel watching it.