Supernatural was never about monsters or epic lore, or angels and the apocalypse. At its core, the series was about family, plus freewill vs the vagaries of fate. It was the Impala and impossible choices. And two brothers who found hope in heartbreak, tenderness despite the trauma, and each other at the end and beginning of every fight and fall. Don’t get me wrong, it was great fun to watch them hunt wendigos and go up against angels and befuddle Crowley (Mark Sheppard) time and again. But the moments, the episodes that really stuck were the ones that often left us a weeping mess on the floor for days.
Like all good scars, these episodes remind us of their presence in the unlikeliest moments, hurting just like the day they were first branded in our memories:
1) “All Hell Breaks Loose, Part 2” (Season 2, Episode 22)
This was one of the first episodes that made me stop seeing Supernatural as just a fun monster show. Dean (Jensen Ackles) sitting beside Sam’s (Jared Padalecki) lifeless body, completely shattered, was heartbreak in real time. His voice cracks, his words stumble. There’s no cool hunter facade here, just raw, unbearable grief. You feel every second of his desperation, every ounce of love that drives him to make a deal that will cost him everything.
What made it worse was knowing this wasn’t just about saving Sam. It was about Dean not knowing how to be without him. That demon deal was the beginning of a long, painful spiral, and we didn’t even realize it yet. This episode perfectly encapsulates the heart of the show: the Winchesters choosing each other over and over, even when it destroys them.
2) “Heart” (Season 2, Episode 17)
This one crept up on me. Sam opens his heart a little, which is rare enough, and we get to see him with someone who brings out his gentle, hopeful side. But of course, it’s Supernatural, so that sliver of happiness is short-lived. When Madison (Emmanuelle Vaugier) asks Sam to kill her before she loses control, the heartbreak is quiet, personal.
The part that truly stuck with me was how Dean waits outside, giving Sam space but carrying the weight too. You see him flinch when he hears the gunshot. The silence that follows is deafening. It’s one of those moments where the show reminds you that saving people doesn’t always feel like winning. It’s duty in the face of heartbreak. It’s mourning yet doing the right thing anyway.
3) “Swan Song” (Season 5, Episode 22)
This episode feels like a series finale because it was meant to be one, and emotionally, it absolutely delivers. Everything leads up to that final confrontation between Sam/Lucifer and Dean. Sam manages to break through by remembering something so simple: the toy army man stuck in the Impala’s ashtray. It’s a simple reminder that even in a show filled with angels and demons, it’s the human moments and connections that matter most.
What was especially heartbreaking to watch was Dean’s decision to be there for Sam, even if it meant watching him fall into Hell. And then that final scene with Sam standing outside Lisa (Cindy Sampson) and Ben’s (Nicholas Elia) home, just watching. Not saying anything because he didn’t need to for us to understand the silent heartbreak of seeing Dean happy, truly happy in a life that he’s not a part of anymore.
4) “Abandon All Hope” (Season 5, Episode 10)
You start this one thinking maybe, just maybe, they’ll pull it off. Jo (Alona Tal), Ellen (Samantha Ferris), the Colt, Lucifer (Mark Pellegrino) in their sights. There’s momentum, there’s fire. And then Jo is hurt, and you realize no one is safe. Her death would’ve been hard enough, but Ellen choosing to die with her daughter? That’s where it hits the hardest. Their goodbye is one of the most tender, courageous moments the show ever gave us.
The aftermath is just as powerful. The way they look when Bobby (Jim Beaver) throws their photo into the fire speaks volumes for their grief. It’s devastating in its simplicity. The show doesn’t dwell on their pain with monologues or dramatic scoring, it just lets it be. And somehow, that restraint makes it hit harder.
5) “Death’s Door” (Season 7, Episode 10)
Even in a show full of death and loss, I think no one expected Bobby to really die. He was always the rock, the one who holds the fort and keeps the porchlight on so the boys could always find their way home. But then the show did the unthinkable. But not before ripping our hearts out in the moments before he is gone. His regrets, his grief, his love for the boys — it all came pouring out as he wandered through his memories. Watching him revisit his childhood trauma and the quiet joy of watching a young Dean play catch was gutting.
And then came the moment he woke up just long enough to say “Idjits.” Classic Bobby. But behind that laugh was something deep and devastating. After all, that wasn’t just a nickname. It was love. It was goodbye. It was everything Bobby wanted to say without getting sentimental. And when the flatline came, it wasn’t just his heart stopping. It felt like ours did too.
6) “Sacrifice” (Season 8, Episode 23)
So much of Season 8 is about guilt, distance, and the unspoken tension between the brothers, and the finale cracks it all wide open. As Sam prepares to finish the trials, fully ready to die, Dean begs him not to. Not as a soldier, not as a hunter, but as a brother.
For once, there’s no yelling or blaming. Just fear, love, and vulnerability. The moment feels hard-earned. After a whole season of the two drifting apart, we see them choose each other again, despite everything. It’s when we realise all over again that the show’s real magic isn’t in the spells or sigils. It’s in the strength of family, in love that doesn’t quit, even and especially when it gets hard.
7) “Dark Side of the Moon” (Season 5, Episode 16)
This episode is a slow emotional burn. Sam and Dean die and end up in Heaven, but instead of paradise, they’re thrown into their own fractured memories. This is when Dean realises a heartbreaking truth. While Sam’s happiest moments are when he’s away from the family, Dean’s are filled with them. And that disconnect? It’s jarring. You realize these two have loved each other fiercely, but never exactly understood each other.
It doesn’t end in a fight. The realisation just sits there. Uncomfortable. Honest. You realise that Dean is losing faith in the one thing he thought he could always count on, that it’s him and Sam against the world, apocalypse or not. This episode doesn’t give you easy answers. There is resentment; there is love. And there is the uncomfortable realisation that, while the boys have always had each others’ backs, their unique traumas shaped them into two very different people, creating a palpable distance between them, one they aren’t sure they can bridge this time.
8) “The Song Remains the Same” (Season 5, Episode 13)
This episode is about a heartbreak that spans generations. When Sam and Dean go back in time to protect their parents from Anna (Julie McNiven), it becomes clear this isn’t just a mission. It’s a rare chance to see the family they lost. Watching them interact with a young Mary (Amy Jaclyn Gumenick) and John (Matthew Joseph Cohen), knowing everything the latter don’t, hurts in ways I didn’t expect.
And when Mary realises the truth, that her sons are standing in front of her, all grown up, it’s gut-wrenching. You can see the fear in her eyes. She realises she’s marked for tragedy, and that her children will carry that burden long after she’s gone. It’s a moment of clarity that hurts more than any monster ever could.
9) “In My Time of Dying” (Season 2, Episode 1)
This episode picks up in the aftermath of Season 1. Dean’s stuck in a ghost-like limbo, watching his family struggle to keep him alive. John (Jeffrey Dean Morgan), for all his flaws, is suddenly more vulnerable than we’ve ever seen him. When he makes that deal with the demon to save Dean, it’s heartrending, not because he dies, but because it’s the one time we seem to act purely out of fatherly love since Mary’s (Samantha Smith) passing.
And yet he still can’t say it outright. Instead, after making Dean promise to take care of Sam and apologizing for making him grow up too fast, he whispers something in Dean’s ear. Then he’s gone, leaving a hollow ache behind. We don’t hear his final words, but Dean’s reaction says enough. That silence was louder than any reveal could’ve been. It’s a messy, emotional episode that captures what the Winchesters are all about: doing the wrong thing for the right reasons, and carrying the fallout forever.
10) “Carry On” (Season 15, Episode 20)
Say what you want about the final season, but “Carry On” delivered the emotional closure we didn’t know we needed. Dean dying on just another hunt, with his brother by his side, was oddly fitting. There is no blaze of glory. No apocalyptic implications. Just a Hunter going down the only way he knows — fighting. Every word he says to Sam shows his obvious pride in his younger brother. But it also shows he is tired. So, Sam tells him it’s okay, because that’s the only way Dean would stop holding on.
In the scenes that follow, we watch Sam grow old without him, every moment chipping away at our hearts. And then it’s his time. When his son, Dean (Spencer Borgeson), tells him it’s okay to let go, and he does, we realise that things had finally come full circle. The end is nothing grand. It’s a hug and a reunion and a rest well-earned.
You can stream Supernatural on Prime Video.
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