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.

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. 

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.

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.

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?

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."

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.