SUPERNATURAL THURSDAYS -The 5 Most Heartbreaking Moments


SUPERNATURAL has given us a lot of great laughs, a lot of brotherly love, and some shocks that made the fandom FREAK out. And then there have been those moments that have left us weeping into our laps. That’s what this week’s Supernatural Thursday is about – those heartbreaking moments that we all know and love (even thought they turn us into hot messes).

Even though these moments are some of the saddest in the series, let’s be honest here – is there anything the fans like more than seeing those boys cry? And now, in no particular order, 5 Heartbreaking moments of Supernatural.


Swan Song

In Swan Song, Lucifer has taken over Sam and the brilliant plan is to have Sam jump into hell after Dean opens the door. Well, things don’t work out the way the boys planned, and Lucifer takes complete control over Sam’s mind and body.

However, after killing Bobby and Cas, and after beating Dean to a pulp, Sam is just about to lay the final punch on Dean when something from the backseat of the Impala catches his eye. It’s a plastic army man that Sam had jammed into the ashtray when he was little, and it’s stayed there ever since.

That little army man brings back a flood of memories, and is what allows Sam to reign in Lucifer and take control to say goodbye to Dean and jump into hell to save the world.


Dean in Hell

The finale of season three left us with one of the most shocking moments (Dean getting ripped apart by hell hounds) and also one of the most heartbreaking. While seeing Dean being torn to ribbons was pretty bad, as well as Sam’s reaction once he realized what had happened, it wasn’t until right before the credits rolled that the worst part of the episode aired.

We expected hell to be a horrible place. It is, after all, hell. However, I think I can say that none of us expected to see Dean, brave, unshakeable Dean, suspended by hooks through his skin in a web of metal chains.

Did I mention he was screaming for Sam? Yeah, that was horrible. Thanks, Kripke.



Through the entire first season from the tip off, Supernatural was about Sam and Dean trying to find their father. They succeeded, and we as a fandom realized why they were estranged in the first place. The entire Winchester clan is just too strong willed to be under one roof, I think we can all agree.

That, and the fact that the demons, etc. know that the boys (John included) are just WAITING for the opportunity to sacrifice themselves for their family… so it probably was best that they weren’t together. But, the three men end up working a few cases as a family, and finally find the demon that started the entire thing.

They don’t kill it, but do almost die trying. So badly in fact, that Dean is left comatose in a hospital ward. John summons old yellow eyes, who makes him a deal (see above paragraph, first line). John’s life for his son’s. Of course, John agrees, but Sam and Dean don’t know the details.

All they do know is that one minute John is fine, and the next minute their father is dead and Dean and Sam are now orphans. Not only was John’s death HORRIBLE, but the guilt that ran through Dean after the incident was heart wrenching.



In Heart, Sam meets Madison, a seemingly normal girl. Her boss has just died, and it looks like it’s from a werewolf bite, and Madison’s ex-boyfriend seems like he’s the one running around looking for some hearts.

Sam and Madison spend some time together, and Sam ends up really, REALLY (REALLLLLLY) liking this girl (don’t get me started on how he “fell in love with her” in like three days. I will go on a tirade and it won’t be pretty). Just one small problem.

She’s a werewolf.

Not THE werewolf, but A werewolf, and after exhausting all of their options (killing the wolf that started the strain, etc.) Sam, Madison, and Dean all realize that the only way to keep her off of the streets and not killing people is by killing her. She begs Sam to end it, to shoot her, and instead, he walks away.

Talk about heavy. Dean offers to “take this one” so Sam doesn’t have to deal with it, and in a tear induced haze, Sam shakes his head, saying that she asked him, he has to do it.

Queue more tears, and then Sam disappearing. A gun shot is heard, and I don’t know who is more heartbreaking, Sam or Dean.



From the beginning, Dean has always worn an amulet around his neck. We learned in season 3, that Sam gave it to Dean during a particularly rough Christmas season. The necklace was actually meant for John, but when he doesn’t show up… again… Sam takes it and gives it to Dean.

As if that weren’t heartbreaking enough.

Then we have the fifth season. Sam has done some stuff, Dean has said some stuff, Cas has borrowed the necklace to find God, only to return it stating that God isn’t anywhere around… and just when you think THAT conversation can’t get any more depressing, Dean walks out of the hotel room.

He’s just at the door when he purposefully dangles the necklace over the trashcan and lets it fall – the noise making a sickening metallic clanging noise as Sam’s gift now lays alone in a dingy hotel room.

The way that Dean trashes the necklace is what makes this so sad. He thinks about it for a split second before letting it drop, but he sets out with conviction to throw that thing away, almost to hurt Sam on purpose.


So there you go. Five heartbreaking moments of Supernatural. I’m thoroughly depressed now, so I may go eat a gallon of ice cream.

There were more that obviously should be added – Ellen and Jo, Sam and Dean parting ways, Dean packing up his things to send to Bobby. Let me know what you would have added to this list in the comments below!

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