If you want to have your heart stomped on more times than you can count only to come back for more, then all you need to do is watch The CW’s Supernatural and you’re good to go. While it features monsters and demons, the show’s most memorable moments have been the emotional ones.
Generally, the saddest scenes are those that concern the main characters being separated, or where they are in mortal peril. And yet, Supernatural concocts a creative array of ways to break our hearts, and you can find 10 of these instances on this list.
John Winchester's Death
The first brush with reality that we got from Supernatural was the death of John. Before this, we’d come to believe that the main characters only died temporarily, and this would be reversed. However, we were in for a rude awakening.
John’s death made it abundantly clear that we were on course for a lot of heartbreak on this show, and the sight of him lying on the ground with no signs of life will always be etched in fans' minds. The knowledge later on that John spent over a century in Hell being tortured by Alastair only shattered us further.
Dean Mourns Sam's Death
Our worst fears came true when we saw Sam bite the dust in the Season 2 finale. The flip side was that it wasn’t Sam’s death that broke our hearts, but Dean’s reaction to it. Dean’s one purpose in his existence was to keep Sam safe, but he witnessed his little brother get stabbed right before his eyes.
The truly sad part arrived when we saw Dean talk to Sam’s lifeless corpse as if he was still there; Dean was in denial and nothing could change his mind. Wracked with enormous grief, Dean went on ahead and sold his soul for eternity in Hell just so Sam could come back.
Dean Kills Himself For Sam
Dean’s penchant for sacrificing himself for Sam is never going to go away, no matter how old they both get. In Season 11, Dean once again put his own soul at risk when he died so that he could bargain with Billie the Reaper to bring Sam back.
It started out with Dean breaking down at the sight of Sam’s body, then heading over to the local hospital to find pills to overdose on. The twist here was that Sam wasn’t even dead, and Dean had taken his own life for nothing. Fortunately for him, he was resuscitated and avoided heading to the Empty like Billie had wanted.
Jack Realizes Dean And Sam Betrayed Him
Poor Jack really got the worst deal when he burned his soul off to save Sam and Dean, only for the two to betray him and lock him in the Malak box. As it happened, Jack without a soul turned into a weapon of mass destruction, who mistakenly killed Mary Winchester; this brought the vengeance of Dean toward Jack.
Still, the innocent boy trusted Sam and Dean, and took their word that they were placing him in the box only temporarily until they could cure him. When trapped in there, Jack realized he’d been had, and broke down in tears as he realized the guys he thought of as fathers meant to trap him in this box forever.
Sam And Adam Fall Into Lucifer's Cage
Had Supernatural ended in Season 5 as Eric Kripke had envisioned, then this would have been the saddest thing ever to happen on the show. Despite that, we still remember when the finale had us believe Sam was trapped in Hell with Lucifer for eternity.
It was a perfectly executed scene, as Sam took control of his body back from Lucifer after remembering his love for Dean, who could do nothing but watch from his bloody and bruised face as both his younger brothers fell into the deepest part of Hell. In that one moment, Dean’s entire reason for living went up in flames.
Dean Realizes He Isn't In Sam's Heaven
Dean had always been insecure that Sam’s true wish was to be away from him. While he understood Sam’s problems with John, he hoped Sam would have Dean in his heart. Unfortunately for Dean, his worst thoughts came true and he realized Sam didn’t think of Dean the same way Dean thought of him.
While Dean’s first memory in Heaven was Sam, Dean himself was nowhere to be found in Sam’s Heaven. Instead, he was heartbroken to see that Sam’s greatest memories comprised of the moments where he was away from Dean. In denial, Dean even tried to argue with Sam’s subconscious that he was his family and that it was them against the world. But a deeper part of him knew inwardly that this was just not the case.
The Leviathans Cause Castiel To Explode
The heartbreaking sentiment here is more meta than in-universe, as the fandom was distraught to find out that Misha Collins would be exiting the series for a long time following this episode.
This made it all the more saddening to see Castiel lose control of his vessel, and then traipsing over to a lake where his face was spilling black ooze. The fans’ last hopes of seeing Castiel emerge alive from the Leviathans’ grasp were extinguished as his body exploded and it appeared as if Misha Collins had walked away from the show for good.
Dean's First Death
Well, more like Dean’s first permanent death, but either way this one hit us the hardest. Supernatural had swerved over Sam’s death in Season 2 to give hope to the viewer that Season 3’s finale would have something similar happen to Dean, only to kill him off in the most violent way possible.
Dean would be ripped apart by a Hellhound, and all the while Sam was forced to watch his brother be torn to shreds. It was a horrible sight for any Supernatural fan, and one we still can’t watch without grimacing as we see Dean be reduced to a bloody pulp — and then he got tortured in Hell for 40 years.
Lucifer Drives Sam Insane
Sam Winchester is a fighter. Like his father and brother, Sam never goes down without fighting and you can count on him to keep his head high. However, Lucifer knows just where to land his punches in the right places, and he reduced Sam to a defeated, sad shell of a person.
It was dreadful to see Sam look so defeated. He had no reason to live, as Lucifer ensured Sam couldn’t even have a meal since he made him see maggots in his food. Seeing Sam's situation through his eyes, even the viewer wanted him to pass away so that his mental torment would finally end.
Dean Calls Sam A Monster
No matter what happened, Dean and Sam were the ultimate team. At least that’s what we thought until this moment happened. After an entire season’s worth of tension between them, Sam and Dean had an explosive confrontation over Sam drinking demon blood. Dean, always having poor choice of words, couldn’t convince Sam otherwise, resulting in Dean dealing him the ultimate emotional blow.
Dean called Sam a monster: someone who wanted to kill not because he thought he was doing it for the right reasons, but because he enjoyed it. Sam was hurt beyond measure at these words, before turning his sadness into rage and inflicting a bloody beatdown on his brother. The unbreakable bond was at last broken.