While there are plenty of sad moments in episodes where Supernatural’s major characters die aren't the worst thing in the show – especially when it happens to Sam and Dean for the second (or hundredth) time.

However, the magic behind Supernatural allowed for greater stories to be told through things like alternate universes and the moral grayness of human-like monsters, and it is these stories that brought about the saddest moments for Supernatural fans outside of characters dying. From Dean's “I wish I couldn't feel a damn thing” speech about Hell to Sam's quiet struggles with the hunting life, there are plenty of heartbreaking scenes in Supernatural.

10 “What Is and What Should Never Be”

Season 2, Episode 20

When Dean is captured by a Djinn in season 2’s “What Is and What Should Never Be,” we are introduced to a reality in which Sam and Dean Winchester never had to hunt monsters and instead grew up with a fairly normal childhood with both parents alive. This presented a bittersweet look for fans as it showed everything that the Winchester family could have had if Azazel hadn't killed Mary. However, the dream also presented an alternate version of Sam Winchester, who was not as close to Dean.

Supernatural’s “What Is and What Should Never Be” episode title is a reference to the Led Zeppelin song of the same name.

The fact that Dean almost considered staying, even though he'd die in real life, showed us how much he wanted this reality to be true. The matter was only made worse by his family begging him to stay. But in the end, knowing that everyone they'd saved was now dead, and he would never have that same relationship with Sam, causes Dean to sacrifice the one thing that would make him truly happy, leaving us in tears.

9 “Heart”

Season 2, Episode 17

“Heart” is arguably one of the first episodes of the show that caught us all off guard, and it is a defining moment in Supernatural history. Originally set up to be a basic “monster of the week” type of episode, “Heart” becomes so much more when Sam and Dean realize that the victim in their case is actually the killer. Having been turned into a werewolf, Madison had been unknowingly killing people while the Winchesters were protecting her.

Madison is a fairly likable character in the episode, and Sam even sleeps with her, making her the first woman he’s truly been with since Jess died. Therefore, when they are all confronted with the fact she is the cause of the murders, the Winchesters are reluctant to kill her, even despite Madison asking them to. Having built up such a sweet relationship between the pair, seeing Sam tearfully walk off-screen and Dean flinch at the gunshot broke us all and demonstrated Supernatural’s emotional capability.

8 "Swan Song"

Season 5, Episode 22

Following the season-long build-up, Supernatural's season 5 finale sees the emotional conclusion to the Apocalypse story arc. Left with no choice, Sam agrees to let Lucifer possess him in the hopes that he can overpower him and lead him into the Cage. Dean s a Michael-possessed Adam and a Lucifer-possessed Sam at Stull Cemetery to be there for his brother during the fight. Although both Archangels scoff at Dean's idea, it does pay off.

“No doubt; endings are hard. But then again... nothing ever really ends, does it?” - Chuck

While Lucifer beats Dean up, a glint from the Impala makes him focus on the toy soldier in the ashtray. What follows is a purely bittersweet flashback sequence of Sam's happiest times with Dean throughout his life, which gives him the strength to take control and send himself and Michael careening into Lucifer's Cage. Sam's ultimate sacrifice and Dean's utter devastation makes “Swan Song” one of the best episodes in the Eric Kripke-era of Supernatural, as well as the saddest.

7 “Regarding Dean”

Season 12, Episode 11

Interestingly, this Supernatural episode doesn't contain a major character death, but it still made me emotional. After being cursed by a witch, Dean slowly begins to lose his memories while Sam and Rowena desperately try to rectify the situation. “Regarding Dean” sees Dean hilariously fumble for the word “lamp,” instead designating it a “light stick” and finding solace in watching Scooby-Doo happily. At one point, he even compliments Rowena's hair, much to her delight.

The tone of this episode puts it on par with “Mystery Spot,” another funny episode that quickly took a dark turn.

However, what begins as a funny scenario quickly turns sad when Jensen Ackles delivers a heartbreaking monologue into the mirror as he desperately tries to who his family is. The tone of this episode puts it on par with “Mystery Spot,” another funny episode that quickly took a dark turn. Dean's distraught expression tugged on everybody's heartstrings, as Dean actually became happier when he ed less, showing how much baggage the hunter is burdened with daily.

6 “Abandon All Hope”

Season 5, Episode 10

“Abandon All Hope” will forever be among the most well-known episodes of the show because it contains one of the most traumatic moments in Supernatural. When Team Free Will finally tracks down Lucifer, they gear up for what could be their last night on Earth. Ellen and Jo Harvelle, who have been away from the show for a while, following the Roadhouse’s destruction, re the Winchesters and Castiel for the showdown.

Unfortunately, Jo is fatally wounded by hellhounds, and the group has to take shelter in a store while they plan their next move. Realizing the gravity of the situation and that her wound is too much to deal with, Jo suggests that she stay behind to set off their homemade bomb, giving the Winchesters and her mother time to escape. But Ellen would never let Jo die alone, and their final mother-daughter scene together before the bomb goes off makes us cry every time.

5 "Sacrifice"

Season 8, Episode 23

Supernatural’s season finales often deliver heartbreaking endings, usually concluding with the death of Sam or Dean. Season 8’s “Sacrifice” was heading the same way, as Sam prepared to complete the Trials to seal the gates of Hell. The final phase of the Trials required Sam to cure a demon, for which Crowley served as the perfect candidate. However, when Dean finds out that the Trials will kill Sam, he tries to stop him.

“Don't you dare think that there is anything, past or present, that I would put in front of you!” - Dean to Sam in "Sacrifice"

“Sacrifice” explores something that has pervaded the show since Supernatural season 1 - the fact that Sam feels “impure.” To hear Sam say “So?” in response to Dean saying he will die made us all tear up because it showed just how self-sacrificial Sam is due to his low self-esteem. However, when Dean says, “Don't you dare think that there is anything, past or present, that I would put in front of you!” it explicitly acknowledges an unspoken rule for the older Winchester that both warmed and broke our hearts; he will do anything for Sam.

4 "All Hell Breaks Loose - Part 1"

Season 2, Episode 21

Watching Supernatural season 2, episode 2, “All Hell Breaks Loose - Part 1” for the first time had every fan in tears as it marked Sam Winchester's first death. With no real inkling into the "characters endlessly resurrecting" future of the show, Sam’s death at the hands of Jake was shocking. What’s more, “All Hell Breaks Loose - Part 1” also featured the deaths of some of the innocent people that Sam had previously saved, making the entire episode rather downbeat.

Moments before they reunite, Sam is stabbed, and Dean’s agony as he begs Sam to stay with him is haunting

Moments before they reunite, Sam is stabbed, and Dean’s agony as he begs Sam to stay with him is haunting, especially as it’s the first time both the viewers and the Winchesters have dealt with it. The moment was so emotionally charged that Jared Padalecki and Jensen Ackles stated that the hug lasted longer than it needed to at the end because they needed the comfort. Therefore, even when rewatching the show, the episode still brings us all to tears as the younger Winchesters deal with their first time apart, and we know there is worse to come.

3 "Death's Door"

Season 7, Episode 10

Almost anyone will agree that “Death’s Door” has one of the saddest character deaths in Supernatural, and it is one that stays with fans, even with Bobby’s alternate self replacing him in later seasons. Having been shot by the leviathan, Dick Roman, Sam and Dean rush Bobby to the hospital in the hopes of saving his life. While unconscious, Bobby re-lives some of his memories while trying to escape the Reaper who has come to take his soul away, in the hopes he will wake up and give the Winchesters some vital information.

Bobby returned as a ghost in "Party On, Garth" before later being put to rest by Sam and Dean.

As a result, the entire episode works as one big, heartfelt flashback montage. Seeing Bobby with Sam and Dean throughout the years and Bobby finally facing his abusive father while declaring his love for his surrogate sons is bittersweet, as we know the character is on his deathbed. Therefore, when Bobby manages to wake up to give the Winchesters the numbers that relate to the leviathans’ plan, seeing his boys one last time, he whispers a weak “Idjits” before slipping away, leaving everybody devastated.

2 “Despair”

Season 15, Episode 18

While everyone knew that Supernatural was coming to an end with its 15th season in 2020, nobody was prepared for the aptly-named episode, “Despair.” Due to Chuck’s plan of ending the universe, Sam and Jack are left frantically trying to save their friends from phasing out of existence Avengers: Infinity War-style. The fact that they are unable to stop it and instead have to watch as the people they love fade away before their eyes is truly heartbreaking. Meanwhile, Billie is hunting down Dean and Castiel in the bunker, hellbent on killing them once and for all.

Whether you were a Destiel fan or not, Castiel’s final death scene had everybody in tears because you knew he wasn’t coming back this time.

Holing up in a storage room, Cas enacts a plan to save Dean from Billie; by declaring his love for Dean, Castiel experiences a true moment of happiness, which triggers his deal with the Empty to take him away. In doing so, the Empty also grabs Billie, leaving Dean alone in the storage room, grief-stricken. Whether you were a Destiel fan or not, Castiel’s final death scene had everybody in tears because you knew he wasn’t coming back this time, and it truly was the end of Supernatural.

1 “Carry On”

Season 15, Episode 20

Although there was a lot of controversy surrounding the Winchesters’ fates in Supernatural’s finale, as fans disagreed about whether it was the right choice for Sam and Dean, it was still a fitting end to the long-running show. With 15 seasons of history, no matter what the ending was, it was going to leave us all in tears, and “Carry On” delivered. Showcasing the Winchesters’ lives after defeating Chuck, Sam and Dean head out on a normal vampire hunt, finally content that they are in charge of their own stories.

However, the hunt goes wrong when Dean is suddenly impaled on a metal bar mid-fight. The shocking moment is made even worse by the lack of resurrections this time, with Jack being a “hands-off” God and Dean refusing their resurrection habit. Therefore, Sam and Dean’s final goodbyes in Supernatural’s last episode are real and heartbreaking. Yet “Carry On” doesn’t stop there, and neither do the tears, as we also see Sam’s life growing old without Dean before finally reuniting with his brother, at peace, in Heaven, showing Supernatural’s story has finally reached its end.