For a show with the premise of two unrealistically handsome guys going on a monster-killing road trip, Supernatural can sure pack an emotional punch. Throughout its twelve seasons, the show has excelled at mixing action, fantasy, comedy, drama and, indeed, tragedy, and, more often than not, has managed to strike a pleasing balance between all of these elements.
What keeps fans coming back for more, however, is undoubtedly the chemistry between the main characters, which ensures that viewers are invested in the show year upon year. Naturally, with such ionate interest in the misadventures of the Winchesters and their pals, there is sure to be more than a few tears along the way.
As has been pointed out on more than one occasion in the show, being friends with the Winchester Brothers is somewhat of a health hazard and as such, there are plenty of character deaths on this list. Of course, there are also scenes of emotional outpouring, heartfelt goodbyes, and moments of brotherly love.
An honorable mention should go to the sacrifice of Crowley in the most recent season finale as, although the scene in itself wasn’t too much of a tearjerker, the villain’s final “bye boys” line certainly twanged on the heartstrings.
With all that out of the way, here are the 17 Most Heart-Breaking Moments In Supernatural.
17. Dean Kills Sam’s Old Sweetheart Amy
The Romeo and Juliet-esque relationship between Sam Winchester and Amy Pond (no, not that one Doctor Who fans) was a brief but touching arc in Supernatural’s seventh season.
Although the family business may be saving people and hunting things, sometimes the line between those two remits is blurred and, when Amy, a Kitsune, begins killing humans to save her son, Sam gives her a free so long as she returns to her vegetarian ways.
Unfortunately, Sam’s older brother Dean didn’t share this comion, and he makes sure to finish the job, killing Amy and leaving her young son alone with the threat that if he ever kills a human, the hunter will return for him.
When Sam finds out, Amy’s death creates a temporary rift between the Winchesters and the scene itself is as emotional as it is uncomfortable.
16. Castiel Beats Dean To A Pulp
The Angel and Demon tablets were hot properties in Supernatural's eighth season and the forces of both Heaven and Hell, as well as the Winchester brothers, of course, were going all out to grab them first.
After taking charge of Heaven, the angel Naomi begins to manipulate a once-again revived Castiel into doing her bidding, which leads to an emotionally charged showdown between Cas and the eldest Winchester.
With the Angel tablet in touching distance of both men, Naomi orders Cas to kill Dean with his bare hands, and the helpless angel obliges, mercilessly bludgeoning the hunter into a bloody pulp.
The real emotion comes when Dean tells Castiel that he’s part of their family, a sentiment that provides the impetus for the angel to break free of Naomi’s control and, thankfully, heal his heavily injured friend.
15. Benny Goes Back To Purgatory
Benny is arguably the most underused character in Supernatural history, and the friendly Vampire’s return to purgatory is a real tear-jerker. After polishing off Dick, Dean and Castiel find themselves in purgatory, and a flashback reveals that during his time there, Dean cheated on Sam by forging a bromance with Benny in order to escape.
Although the duo keep in touch, Sam’s jealousy forces Dean to cut ties with his new pal, but only until a favor is required. When Sam becomes trapped in purgatory, Dean needs someone familiar with the territory to save his brother, and asks Benny to take a beheading, so Benny can return to that forsaken place and bring Sam back.
Clearly unhappy with his life topside, Benny agrees and, in a heartbreaking moment, Dean lops off his friend’s head with a machete.
14. Dean Loses His Memory
When Dean is hexed by a powerful witch in season 12’s “Regarding Dean”, the effects are not immediately apparent until he slowly begins to forget the simplest of things-- basic words, what key starts his beloved Impala, and how to even drive all begin to slip away.
Initially, the episode presents the funny side to Dean’s troubles with Sam having to label everything in their motel room and Dean freaking out because he thinks he’s never seen a dead person before.
However, it soon becomes clear how devastating the situation could become. As Rowena explains to Sam, eventually he would be unable to speak or swallow and then Dean would eventually die (to which Dean even remarks, “sucks for that guy!”).
The most emotional moment comes when Dean looks into a mirror, repeatedly trying to remind himself of who he is, along with his family and friends, to the point where he’s tearfully unable to even recall his own name.
13. Dean Stops Sam From Closing The Gates Of Hell
Closing the gates of hell would certainly make a Winchester’s job easier, but as far as Dean is concerned, the price isn’t worth paying. With his brother Sam on the verge of completing the third trial, Dean bursts onto the scene and gives a heartfelt monologue about how he simply cannot afford to lose his brother.
Supernatural is no stranger to such sibling outpourings, and the show is built upon a cycle of the Winchesters being at odds and then making friends by the season finale, but this church scene perhaps packs more impact than usual, with Dean leaving his heart bare in an attempt to prevent Sam’s sacrifice.
The scene is even more emotional due to Crowley’s creeping shift towards humanity as Sam’s ritual begins to take hold, with the King of Hell slowly beginning to realize the pain he has caused.
12. Lisa And Ben Forget Dean
When Sam took one for the team and dragged Lucifer into the cage, Dean took his brother’s advice and attempted to settle down into a normal life with previous one-night stand Lisa and her son, Ben. Dean’s new family life seems to be going swimmingly until a soulless Sam reemerges, and the Winchesters resume their hunter lifestyle.
After trying, and failing, to balance killing the supernatural with being a family man, Dean realizes Lisa and Ben are in too much danger, mostly from himself, and, after Lisa almost dies, he asks Castiel to erase the mother and son’s memories of him.
The hospital bed scene where the duo treat Dean like a total stranger is the moment that really opens up the tear ducts and has fans wishing the Winchesters could catch a break.
11. Dean's (First) Death
The Winchesters have died, or been sent to the afterlife, so often during Supernatural’s twelve seasons that such events don’t really come as a surprise these days. However, it wasn’t always this way, and Dean’s first demise was a bona fide tearjerker.
After selling his soul to revive the fallen Sam, the time finally comes for Dean to keep his end of the bargain and he is ultimately sentenced to a vicious death via Hellhound. The actual act is more B-movie gruesome than emotional, but it’s the aftermath that really brings the pathos.
With his brother in tatters, a heartbroken Sam witnesses the death of his beloved sibling for the first time, and the final sting of Dean being chained up in hell only adds to the scene’s trauma.
10. Dean its To Torturing Souls In Hell
As tough as Dean’s death was for fans, things didn’t exactly get much better after his inevitable revival. The eldest of the Winchester brothers was clearly traumatized by his time in hell, and it is soon revealed that after thirty years of torture at the hands of the demon Alastair, Dean relented and became a torturer himself, doing unspeakable things to innocent souls.
After many episodes of this truth weighing heavily upon Dean, the burden is finally lifted somewhat during one of Supernatural’s classic “beer by the Impala” sessions. Dean’s confession is completely harrowing, with genuine emotion plastered all over the character’s face.
According to Jensen Ackles, the scene was incredibly difficult to film and required multiple takes and several time-out sessions in order to get right.
9. Castiel Says Goodbye To The Winchester Family
There have been many near-death encounters for the protagonists in Supernatural but few as emotional as the time Castiel was struck by the Lance of Michael in season 12 episode “Stuck In The Middle (With You)”.
Crowley explains to Castiel and the Winchesters that the weapon causes bad beings to die quickly and good beings to die slowly, and, unfortunately for him, Cas falls into the latter camp. The Winchesters can only watch helplessly as Castiel pleads with them to save themselves, as he doesn’t want his last moments to be spent watching his “family” die.
Cass thanks the brothers and Mary for giving him the best years of his long life, telling them that he loves them and instructing them to keep fighting.
Obviously, the boys refuse, reminding him that Winchesters don’t leave family behind. For an angel rejected by lots of his celestial kin, it was clear in this moment how much Castiel’s surrogate human family mean to him.
8. Sam's (First) Death
As the first of the Winchester brothers to bite the dust, Sam’s demise in season two’s “All Hell Breaks Loose Part 1” came as a complete and genuine shock. The two-part episode finally provides some much-needed answers surrounding Sam’s psychic abilities and the mysterious demon Azazel, and brings together all of Yellow Eyes’ chosen children.
With a Battle Royal triggered to allow the demon to find the most worthy soldier, Sam is murdered by fellow competitor, Jake. The scene is extra emotional due to the fact that Sam previously had an opportunity to finish Jake off, but opted for mercy instead. Indeed, Sam’s comion is what ultimately gets him killed.
Predictably, it’s the reaction of the surviving brother-- Dean in this instance-- that really hammers home the tragedy of the moment, and his pained reaction is truly upsetting.