The Saddest Moments On Supernatural

Let's face it: Supernatural fans who claim they've never cried during the series are probably lying. With 15 seasons of deaths, apocalypses, and heartbreaking goodbyes to the show's name, shedding a single tear or two is par for the course. In just the first five minutes of the series, we see the Winchester family ripped apart by tragedy as Mary Winchester gets flung on the ceiling and consumed by sentient fire. Just a typical Thursday in the lives of the Winchesters.

The tragedy doesn't end there, though — not by a long shot. That opening scene sets the tone for what's to come in the series as a whole. Between the numerous deaths of the Winchester brothers and the losses they endure on the road to ridding the world of monsters, there's a whole lot of heartbreak to go around.

Grab several boxes of tissues, because we're about to ride down memory lane in a '67 Chevy Impala with classic rock crooning in the background. These are the saddest moments from Supernatural's 15 seasons. And we'll never be ready.

Beware: Spoilers through the Supernatural series finale.

Heart to heart

It's bad enough when the brothers have to witness death, but it's even worse when they have to cause it — especially when it's someone they care about. Sam's bad luck with the ladies is no secret, but by season two, he's watched at least two of his girlfriends die. 

Sam has a fling with a woman named Madison during a run-of-the-mill werewolf hunt in "Heart," but, as it turns out, she's the werewolf. She proceeds to go on a killing spree when she unknowingly turns. Talk about a mood-killer. After the brothers fail to cure Madison, she begs Sam to kill her — and she's adamant that he be the one to do it. Of course, Dean offers to step in, but Sam is determined to honor her final wish. And he does, as Queensrÿche's "Silent Lucidity" plays in the background.

While we blessedly don't have to watch the final blow, we hear the harsh shot of a gun go off after Sam's tearful exchange with Dean. Sam ditches the patented Winchester single man tear for full, heavy sobbing — even Ackles sheds an unscripted tear. As Jared Padalecki revealed to TV Line, "I think 'Heart' was probably the most I cried that was used." That's seriously saying something.

Baby's first death

By season two, we've already seen our fair share of deaths: There's Mary, Jess, John, Madison, and almost Dean — but John's sacrifice and his pesky demon deal prevent the eldest Winchester brother from taking a trip to the pearly gates early on. So, when Jake quite literally stabs Sam in the back so he can reign as Demon Blood Child Supreme, no one expects Sam to meet a premature end. Yet he does, and it floored the fandom.

Sure, death is a little less hard-hitting when anyone and their mother can make a demon deal, but Sam's season two death marks the first time a brother actually physically dies. It seemed a lot more permanent than it would turn out to be, back then. Additionally, the series' future was uncertain at this point, and it wasn't known if Jared Padalecki would be signing on for a new season.

Thus, fans had more questions than answers when Dean screams, "No!" and holds his baby bro while he dramatically dies in the rain. Their patented brotherly angst instrumental mix plays while Dean lies about how bad the situation is. He bellows, "Sam!" into the abyss when Sam takes his last breath. Of course, everything is "fine" just one episode later when Dean follows in Daddy's footsteps by making a demon deal to bring Sam back to life. But it was a real bummer at the time. 

Hellhound on Dean's trail

As they say, no good demon deal goes unpunished. Despite Dean's crossroad demon deal in season two being pretty ironclad, the fandom couldn't help but spend the entirety of season three thinking the elusive Winchesters would somehow evade Dean's crispy fate in the 11th hour. Unlike most 10-year demon deals, Dean gets to live for "one year, and one year only" after bringing his brother back from the dead. The demons have an apocalypse schedule to follow, after all.

Between episodes like "Ghostfacers" and "Time Is On My Side," Dean has a lot of space to deal with his impending death — but that doesn't make it any easier to swallow when the day comes in season three's "No Rest for the Wicked." In one of the most brutal main character deaths on the show, we see Dean get ripped apart by Lilith's invisible hellhounds.

After Sam weeps over his brother's dead body, which he blames himself for, the season closes on Dean screaming for help in Hell. While we witness Sam watch Dean die dozens of times in "Mystery Spot," the real thing is a lot harder to stomach than Gabriel's twisted antics.

A mother-daughter sacrifice

You'd be hard-pressed to find healthy parent-child relationships in most of Supernatural, but Jo and Ellen Harvelle are the best mother-daughter duo around. That is, until a hellhound rips Jo limb from limb, and viewers have to watch the young hunter die a slow, painful hero's death in season five's "Abandon All Hope." In that moment, the fandom did, indeed, abandon all hope.

As Team Free Will races against the clock to take down the Devil himself, Satan's guard dogs are hot on their trail. The Dark Prince must have been skipping out on the kibble, as the hellhounds take out a massive chunk of Jo's intestines. Not wanting her impending death to be in vain, Jo decides to sacrifice herself with a bomb to destroy the hellhounds and give the Winchesters a head start against Lucifer.

However, Ellen is unwilling to live a life without her daughter, and so she waits with Jo, volunteering to set off the bomb. Indeed, Jo doesn't survive long enough to do it herself — but ultimately, both of the Harvelles' sacrifices are for naught. The Winchesters soon discover that their demon-killing Colt is useless against Satan himself. As two of the few early characters who were still alive, the Harvelles' deaths cut deep and long. Raise your hand if you're still not over it.

Swan diving into Hell

The season five finale is exceptionally hard-hitting, as it was creator Eric Kripke's goodbye to the series. Anyone can tell you that self-sacrifice is the Winchester way, and both Sam and their half-brother Adam take a swan dive into Lucifer's cage to protect the world from Luci and Michael's toxic vendetta. With that, the youngest Winchester brothers are sentenced to a hellish prison mind-meld with the two most powerful angels in the biblical mythos. While Sam shows up at the end of the episode, crashing Dean's normal life with his girlfriend Lisa and her son Ben, we don't see Adam again for years. Sam is busy making the lights flicker when he mysteriously shows up, so we do know that all is not right in Whoville.

Alongside the episode's two sets of brother drama (biblical and human), fans are also treated to Chuck's chilling narration, about how vital the Winchesters and their trusty Impala are. Chuck, the figure that fans assumed was God (and a metaphor for Kripke himself), voices a nostalgia-filled quote: "Nothing ever really ends, does it?" The fandom frequently touts that sentiment today, even after the series' end.

Bobby Singer says goodbye

John Winchester certainly isn't winning any father of the year awards, but thankfully, gruff, baseball cap-wearing Bobby Singer was there to fill in John's parenting gaps. We find out on his deathbed that Bobby himself had a horrible relationship with his dad: Bobby yells at a dream version of his father, revealing that he never had kids because he was too afraid of turning into him. Then, he adds that he "adopted two boys and they grew up great. They grew up heroes. So you can go to Hell!"

The moment offers significant closure and nods at a heartbreaking backstory for the boys' surrogate father. Of course, things get even more emotional when Bobby wakes up from his hospital bed to save the Winchester boys one last time, before succumbing to his head wound.

The most tragic part, though, is Bobby's insistence on sticking around as a ghost to help the boys. Like all ghosts, he eventually stews in his anger so much that he breaches vengeful spirit territory: Sam and Dean are forced to burn his flask so he can pass on. After getting toyed with in Hell and making the rounds in Heaven as an imprisoned spirit, Bobby finally gets peace in the series finale, becoming Dean's heavenly guru.

Kevin can't wait

The angel Gadreel has his fair amount of jerk moments: Between forcing Dean to make a newly human Castiel homeless and murdering teenagers, he's certainly not on anyone's favorite angel list. We've seen a lot of death in Supernatural. A lot. And while Kevin's death isn't the first time a young character bites it, most of the younger characters who die are just one-off guest stars, not a main character we've been following for years.

Even worse? Kevin never wanted this life. He doesn't have a tragic hunter backstory where someone he loved died at the hands of a monster, spurring him into fighting the good fight until an untimely, early death. Nope. He's just a random teenager plucked from his AP life and thrown into the world of prophets, angels, and demons. After Gadreel snuffs Kevin's lights out, Dean tears apart the bunker following his hunter's funeral while the song "Famous Final Scene" plays in the background.

Kevin's death is infinitely more gut-wrenching when we find out that his soul is perpetually in limbo, as Heaven's gates are closed. He supposedly gets a reprieve when Chuck "sends him to Heaven" in season 11, but we find out that this was a lie in the final season. God, ever the vindictive narcissist, actually sent Kevin to Hell — and we never discover if Kevin makes it to Heaven after the new regime takes control during the final episode. Poor Kevin.

The bathtub ballad of Charlie Bradbury

After just one episode, Charlie Bradbury quickly becomes an integral part of the series as the boys' on-call hacker. When Charlie isn't LARPing, she's crafting magical credit cards — at least until she dies.

Like many Winchester allies before her, Charlie is sucked into their apocalyptic drama whenever one of them needs saving. Sam calls on her to help him remove Dean's Mark of Cain in season 10, but she gets murdered by the Stein (read: Frankenstein) family, who are determined to recover the Book of the Damned. The spunky heroine dies in a bathtub, primarily to send Dean into a spiral of anger and violence. That's what the series loves to do when the show needs a shakeup: Regress Dean's character growth by killing someone he loves and having him react badly.

Fans have criticized Supernatural for both its lacking LGBTQ+ representation and how it treats its women — Charlie's death offers harsh blows in both categories. She deserved better, and her death reinforces the rift between Dean and Sam. The eldest Winchester reminisces about their friendship at her hunter's funeral, blaming Sam for her death. Why not use the strong lesbian character to move the brothers' plot forward? Translation: What else is new?

Mommy deadest

Mary fulfills her Winchester destiny at the end of season 11 when Eve brings her back from the dead — but she can't cope with the fact that it's been over 20 years since she died. How does a mother deal with the knowledge that her children magically reached their 30s in what feels like a day?

Mary did everything she could to get out of the hunter lifestyle back in the '70s, and she's crushed that her boys ended up following in her family's footsteps anyway. As far as she remembers, she was tucking baby Sammy into his crib just yesterday, and now he and Dean are seasoned hunters who've both died more than a few times. She can't deal, so she doesn't.

While Dean and Sam are thrilled to get another chance with their long-dead mother, she doesn't even want to take their calls for a while. It's tragic enough how badly John neglected the boys, but after watching Dean put Mary on a pedestal for over a decade, it's defeating to see him fall apart over her rejection. Sam never even got to know her, and this is a bitter introduction for him — especially since she caused most of the drama in his life by making a demon deal. Eventually, they patch things up until she dies again, but at the start, it's a gut-wrenching Winchester reunion.

Dean's widower arc

In the season 12 finale, "All Along the Watchtower," Sam has to pick Dean up and carry him out of the alternate world when Cas faces Lucifer and Dean refuses to leave him behind. The emotional scene mirrors the season one sequence in which Dean drags Sam away from the fire that killed the love of Sam's life, Jess. Dean's look of relief when Cas stumbles out of the rift is palpable — until Lucifer comes after him a moment later, stabbing and killing Dean's angel in front of both Winchesters.

Dean, though, has a look of raw pain that stands out from his usual loss: He's experiencing heartbreak. Then, Mary gets dragged back into the alternate universe with Lucifer while Dean kneels next to Cas' dearly departed body. In the next episode, Dean sets aside his hatred of prayer to beg Chuck to bring back Cas. He only ever sets aside his pride for Castiel. Even though he knows it's futile, Dean checks to make sure his angel is still dead when he goes to lovingly prepare the body for a hunter's funeral.

Like the Winchesters, Cas has died quite a few times in the show. Yet this one cuts especially deep, because it comes out of nowhere and Dean completely falls apart afterward. He refuses to let anyone handle the body and goes through a period of grief so significant that the fandom calls it Dean's "widower arc."

In the arms of an angel

There are many bad dads in Supernatural, but Castiel is not one of them. After Cas makes a deal with the Empty to save his surrogate son Jack, fans wondered what Castiel's moment of pure happiness would be — the moment that would take him from his found family. However, that fateful moment doesn't come until late into the show's final season.

In "Despair," Cas realizes something: "Happiness isn't in the having. It's in just being. It's in just saying it." So he confesses the very thing that he'd been holding back the better part of a decade: Finally, Castiel tells Dean that he loves him. Pure joy is on his teary face, despite his impending death. His mission? Saving Dean, of course.

Castiel realizes that he doesn't need reciprocation for the love he's been shoving down for years. The angel sacrifices himself to the Empty to take Death along with him into the nothingness, in order to save Dean from her icy grip. Dean curls up on the floor in hopelessness in the aftermath — it happens so fast, he doesn't even get a chance to respond. Most fans were curled into a ball too, as they waited just as long as Cas did for their favorite angel to tell their favorite hunter how he really feels. It's all the more agonizing for its finality.

There'll be peace when you are done

Fans weren't sure how Supernatural would end. However, most knew it wouldn't be anywhere near pleasant. From day one, Dean says that he wants to go out in a blaze of glory. Much to the heartbreak of the fandom, he gets his wish, even though he'd finally gained enough self-love to want a life for himself.

While some fans are irritated that a barrage of bullets didn't barrel him down, there's a beautiful simplicity to Dean's death. While they take down a nest of vampires to save a pair of young brothers, Dean is slammed into rebar, leading him to bleed out in front of Sam. Dean begs Sam to let him go with a potent nod to the pilot episode: When Sam says he can't handle life without Dean, Dean assures him that he can, to which Sam responds, "Yeah, well, I don't want to." Everything has come full circle — and it hurts.

Sam lets Dean go, and we cut to a heart-wrenching hunter's funeral where Dire Straits' "Brothers in Arms" plays. If that wasn't enough, Sam grieving in the Impala as an old man makes it even more intense. Then, the brothers reunite on a bridge in Heaven in their pilot clothes. The fandom can't listen to "Carry On Wayward Son" by Kansas or "Brothers in Arms" without turning into a messy puddle of tears — singular man-tears be damned.