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 passionate 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

Jewel Staite as Amy Pond in Supernatural Supernatural: 17 Most Heart Breaking Moments

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 pass so long as she returns to her vegetarian ways.

Unfortunately, Sam’s older brother Dean didn’t share this compassion, 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

Misha Collins as Castiel in Supernatural Supernatural: 17 Most Heart Breaking Moments

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 LaFitte Supernatural Supernatural: 17 Most Heart Breaking Moments

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

Jensen Ackles as Dean Winchester in Supernatural Supernatural: 17 Most Heart Breaking Moments

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

Jensen Ackles as Dean Winchester and Jared Padalecki as Sam in Supernatural Supernatural: 17 Most Heart Breaking Moments

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

Cindy Sampson as Lisa and Nicholas Elia as Ben in Supernatural Supernatural: 17 Most Heart Breaking Moments

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

Jensen Ackles dying as Dean Winchester in Supernatural Supernatural: 17 Most Heart Breaking Moments

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 Admits To Torturing Souls In Hell

Jensen Ackles and Jared Padalecki as Sam and Dean Winchester in Supernatural Supernatural: 17 Most Heart Breaking Moments

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

Misha Collins as Castiel in Supernatural 1 Supernatural: 17 Most Heart Breaking Moments

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

Jensen Ackles and Jared Padalecki as Dean and Sam Winchester in Supernatural Supernatural: 17 Most Heart Breaking Moments

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 compassion 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.

7. Kevin Tran Dies

Orsic Chau as Kevin Tran in Supernatural Supernatural: 17 Most Heart Breaking Moments

Kevin Tran may have been a child genius, a college mathlete, and an actual prophet of the lord but, unfortunately for him, he was also the recipient of a thorough smiting, courtesy of Gadreel.

An immensely likeable character, Kevin was worked to the bone by the Winchester brothers in an attempt to uncover the secrets of the Demon Tablet. Despite treating the boy like a celestial Google Translate at times, Sam and Dean did genuinely care for the youngster.

Perhaps the reason Kevin’s death was so sad is that he was one of the few victims of the Winchester curse who never chose the life of a hunter. The boy wanted nothing more than to go back to his studies and live a normal life, but was forced into the fight between Heaven and Hell, paying the ultimate price as a result.

6. Ellen And Jo Die

Ellen and Jo Harvelle in Supernatural Supernatural: 17 Most Heart Breaking Moments

Mother and daughter hunting duo Ellen and Jo may not have made a vast number of appearances in Supernatural but their rural charm earned the pair a place in the hearts of the audience nonetheless. Fittingly then, their demise was an honorable, emotional, and family-centric goodbye that ensured they went out with a bang.

With Jo already suffering from a fatal Hellhound bite, the young hunter decides to make her last moments count and lure the beasts into an explosive trap. Refusing to let her daughter make this sacrifice alone, Ellen opts to bow out by Jo’s side, and eventually triggers the explosion herself.

The moment neatly sums up Supernatural’s themes of family and sacrifice, but also serves to re-enforce the fact that being around the Winchesters is not good for one’s health.

5. Lucifer Beats Up Dean In Sam’s Body

Jensen Ackles as Dean Winchester and Jared Padalecki as Sam Winchester in Supernatural Supernatural: 17 Most Heart Breaking Moments

Sam Winchester spent an awfully long time resisting the charms of the Archangel Lucifer, but you can’t resist the devil forever and, eventually, the fallen one gained the vessel destined to be his.

Naturally, Dean and Bobby are distraught at seeing their loved one possessed by such a great evil but, before action can be taken, Lucifer effortlessly snaps Bobby’s neck and proceeds to brutally beat the stuffing out of Dean.

With a bloody and disfigured face, Dean reassures his brother that everything is okay and that he won’t leave his brother alone, but, just as Lucifer is about to deliver the finishing blow, his eye-line meets one of Sam’s old toys stuck in the Impala.

This memory trigger gives Sam enough impetus to temporarily shake off Lucifer’s possession. Although it wasn’t too late to save the world, it was too late to stop the audience from being reduced to tears.

4. Charlie Dies

Felicia Day as Charlie in Supernatural Supernatural: 17 Most Heart Breaking Moments

Felicia Day’s Charlie was universally loved by Supernatural fans and an honorary Winchester sister but, in one of the show’s most controversial moments, she was killed off in brutal fashion.

With Sam and Dean attempting to find a way to remove the Mark of Cain, the race to find the Book of the Damned was heating up drastically, and Charlie was instrumental in this endeavor. Also competing for possession of the book, however, was the evil Styne family, and it was one of these villains who murdered Charlie– another example of someone dying in the course of helping the Winchester brothers.

Although the death itself isn’t shown on screen, the tense atmosphere and foreboding sense of doom, mixed with the Winchesters’ helpless and stunned reactions is enough. Sometimes it’s about what you don’t see.

3. John Winchester Dies

Bad TV Dad John Winchester Supernatural: 17 Most Heart Breaking Moments

Supernatural may be well known for frequently resurrecting characters from the dead, but Jeffrey Dean Morgan’s John Winchester has thus far not been one of them, making the patriarch’s death scene in the season two opener all the more powerful.

With Dean at death’s door after a car crash, John does the only thing he can to save his eldest son: he makes a deal with the very demon he spent his life hunting, giving his own life in exchange for Dean’s safety.

The scene between John and Azazel, as well as John’s final goodbye to Dean, are moving enough, but things get even more teary when Sam sees his father on the hospital room floor. The slow-motion coffee drop scene is as classic a death as you’ll find on any small screen drama.

2. Dean Tells His Mom He Hates Her, But Loves Her

Jensen Ackles as Dean Winchester in Supernatural 1 Supernatural: 17 Most Heart Breaking Moments

After Mary Winchester is brainwashed by the British Men of Letters and becomes their emotionless assassin, Dean enters his mother’s head to try and bring the real Mary back.

He finds himself in a perfect fantasy world where Mary is a normal mother to her two young boys, but Dean struggles to get through to the woman, and realizes that she’s choosing the safety of an illusion over the pain of reality.

Dean snaps and vents a lifelong list of hurt and heartache, all stemming from her decision to make a deal with Azazel to save John’s life long before the boys were born. Dean eventually tells her how he hates her, but loves and forgives her regardless, assuring her they can start over as long as she fights back.

In a TV series full of tragedy, this scene stands out as one of the biggest tearjerkers throughout the twelve seasons so far.

1. Bobby Dies

Bobby Supernatural: 17 Most Heart Breaking Moments

He resisted for so long, but eventually even stubborn Bobby Singer succumbed to the Winchester curse. Sam and Dean’s surrogate father and an ever-present member of the Supernatural cast met his end during what seemed like a run of the mill recon mission against the Leviathans.

The death came completely out of the blue, and, throughout the character’s goodbye episode “Death’s Door”, fans were thinking that the show would surely find some fantastical way to save Bobby’s life.

Alas, it wasn’t to be. Bobby’s death was real and, although actor Jim Beaver would later reprise his role as a ghost and in other forms, the character has remained deceased.

The final exchange between Sam, Dean, and Bobby in the hospital as the weathered hunter takes his final breaths is nothing short of soul destroying. We’re not crying, honestly, there’s just something in our eyes…

Supernatural season 13 is set to premiere October 12th on The CW.

Can you think of any other emotional Supernatural moments that had you in tears? Let us know in the comment section!

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