1. Season 2 Episode 22 – Sam

Everyone remembers the season 2 finale, how Dean sells his soul in order for his brother to be able to live. It’s one of the biggest events in all 10 seasons of Supernatural, a catalyst for everything that happens afterwards. It brings us Castiel, the best additional to the show besides Charlie. But, we can’t forget why this event happens in the first place.

Episode 22 of Season 2 is where Sam and the other demon blood children are sent into basically a weird demonic version of The Hunger Games. This is the most emotional death in all of the many death of the Winchester brothers just for Dean’s reaction and the way he clutches onto Sam at the end. If you didn’t get goosebumps, then you don’t get the Ackles/Padalacki love.

2. Season 3 Episode 22 – Dean

Dean dies a lot. More than a hundred times if you count the Tuesdays. But, even without counting those he has more meaningful deaths than Sam. Meaningful in the sense that his deaths change him more profoundly than Sam’s changed Sam. Dean’s Season 3 mauled by hellhounds death scene is not only emotional for his reaction that his time has come, as well as Sam’s, but it’s also a well shot scene with excellent makeup that even made me queasy. Most importantly, this death changes Sam more than any other death in the show.

3. Season 1 Episode 22 – Dean

What a cliffhanger this episode was. The Winchesters are supposed to die by supernatural events, not from something like a car accident, and that’s what makes this episode so hard to choke down. We expect them to get into situations that no one else would get in, but to see Sam and Dean brought down by something so human, so natural is world shattering. It’s also one of the first important deaths in the show.

4. Season 5 Episode 4 – Future Dean

This was one of the first death scenes that actually made me cry/scream. Even though I knew it wasn’t really Sam, it still felt like Sam. Even though it was future Dean, it felt like now Dean, and I didn’t want him to die at Sam’s hands. All the points go to Jensen here for his crazy amazing portrayal of Dean’s inability to look at Sam in any other way than his kid brother who was lead astray. It’s heart-breaking and gut-wrenching, and the very reason why this show is so good.

5. Season 5 Episode 13 – Sam

This death hurts more because we had come to like Anna. She seduced our Dean in one of the best scenes in the entire show, with a definite homage to titanic. We liked her balls and her red hair. Charlie wasn’t even a blip in our radar yet, then she goes and stabs Sam. We know our boys die a lot, but to have someone meant to be a friend do the killing is really the most painful of all.