In honour of the heart-wrenching Supernatural season 6 finale, Neffy and I have decided to compile a list (yes it's a list sue me, they're fun) of the most heartbreaking moments in Supernatural's history. Let me just say, this is not an easy task. Supernatural has some of the most upsetting moments ever to appear on television. It should really be called lets try to break the Winchesters in every way possible, over and over and over again. But then, we love it don't we. As meta fangirl/publisher Sera put it “the best parts are when they cry” (“The Monster at the End of This Book” 4.18).
I should warn you that there are major Season 6 spoilers in this post, so proceed at your own risk...
It really is the most traumatic program on TV, and yet I continue to watch it every week, it's almost like I enjoy the pain. I guess there's really nothing almost about it, I love the pain. I am clearly masochistic, but I'm okay with that. In fact, I am so okay with it that I am going to put myself through the pain all over again just so I can compile a list for the 4 (possibly 5) people who read this blog. And you know what, I enjoyed every minute of it.
Number 10: Jimmy Novak sacrifices everything.
“The Rapture” (4.20)
I love Cas, and I love Misha Collins as Cas, so I don't want him to loose Jimmy Novak as his vessel but that just makes me feel worse about this. Jimmy Novak was a devout man, so when an Angel asked him for a favour naturally he jumped at the chance, he didn't realise the hell that was about to rain down on his poor body. When our beloved Castiel was expelled from his body, and Misha got to talk in his regular voice for once, poor Jimmy thought he was free. Alas no one gets a happy ending on this program, instead his family got kidnapped by demons and he got shot. That's not the worst of it though, as he lay bleeding to death Castiel took over his young daughter's body. Jimmy knew first hand what she would go through as a vessel, so he sacrificed his life for his daughters. I was happy to have Cas back, but I still to this day feel bad for poor Jimmy Novak.
Number 9: Bobby is forced to kill his wife... again.
“Dead Men Don't Wear Plaid” (5.15)
Poor Bobby, I mean this guy almost gets more crap than Dean; he works his butt of for those boys and never gets a moments peace for himself. We know Bobby lost his wife, and that he had been the one to kill her, something that has clearly haunted him since it happened. But does he complain, no, he does his job, maybe he drinks a bit more then most but that seems to be a common trait amongst hunters, Bobby just wants to make the most of a bad situation. So what do the Supernatural writers do, well they raise his wife from the grave, she's alive and well just enough time for Bobby to remember what it was like to be happy, then she turns into a zombie and he is forced to kill her all over again. I'm sorry but that is just fucked up.
Number 8: Sam and Dean break up.
“When the Levee Breaks” (4.21)
I may be more partial to one of the Winchester boys than the other (I'll leave it up to you to guess which one) but I don't like it when they are apart. They're a pair, it's like they aren't whole without each other. Siblings fight, and these two are together so much that they fight more then most, but this moment is different. This is the moment when Sammy picked a demon over his brother. OK so Dean was being his usual righteous self and Sammy was just trying to rebel, but working with a demon... really very not cool. Regrettable things were said by both parties, punches were thrown and man tears were shed. It was so bad they are still trying to rebuild their relationship to this day, fights like this don't just go away. It was honestly like watching my favourite couple break up, sadness abounds.
Number 7: Dean takes out his daddy issues on the Impala.
“Everybody Loves a Clown” (2.02)
Oh Dean, you should really be a poster child for Daddy issues but you'll be damned if your actually going to admit how much of an asshole your father actually was. It's no secret that as a parent, daddy Winchester left a lot to be desired. Sure he loved his boys but he was so hell bent on revenge that he wasn't exactly around that much, which left Dean to basically raise himself and his little brother on his own. That said, I did shed a tear of two when Mr Winchester sacrificed his life for his son. Don't get me wrong, I'm glad he did it because I wanted to see a whole lot more of Dean in my life but it didn't help Dean's issues. All Dean cares about is family and knowing that his father died to save him when he doesn't think he deserved to be saved is almost too much for that poor boy to handle. Not one for chick flick moments (except for all the other times) there's only one way a real man can work through his pain and that's by beating the crap out of something. The reason this moment makes the list is because Dean chooses to take his anger out on the Impala, the car that sometimes seem more like member family then his daddy ever was. When I watch it, I feel like I am the one being beaten.
Number 6: Everything turns to crap aka Dean vs. Lucifer.
“Swan Song” (5.22)
Literally the end of everything, it's the apocalypse, Sam said yes, Michael went and got himself a new vessel and Cas is about to clean out the worlds liqueur stores. Everything about this episode is heartbreaking. Sam's finally become everything that he hates, Dean has lost his little brother and it looks like they have lost the battle to save the world. But it just gets worse, the only way they can save the day is to sacrifice Sam which means breaking up the Winchester brothers and that's never good. Then Cas is blown to pieces, and Bobby gets his neck broken, yeah they come back but you didn't know that at the time. Two things really stand out in the heartbreaking stakes of this scene, the way Dean lets himself get beaten to a pulp still insisting that he is not going to leave his little brother and the look on Sami's face as he makes the ultimate sacrifice. If this had actually been the end of the series, it would have been one of the most traumatic ends ever.
Number 5: Castiel comes clean.
“The Man Who Would be King” (6.20)
This one is difficult to describe, because although we find out about everything in one episode it was really happening for an entire season and when you go back and watch the clues are all over the place. Castiel confesses to the camera, the audience, God and most importantly Dean, that he has been working with Crowley to locate purgatory in order to defeat Rafael and gain control of Heaven. I think the most traumatic part of this confession is that his actions are understandable, I came out of it and I wasn't sure who was right. Dean has always taken Cas for granted, and throughout season 6 he was worse then ever. If anyone was ever in need of a hug it's Cas, his whole world has been turned upside down and he doesn't have anyone else to turn to but by the time Dean realises this it's already too late, it's gone on too long. As Castiel heartbreakingly asks Dean where he was when he needed him and Dean replies that he was there, I wanted to slap him. Cas had been reaching out to Dean for the entire season but Dean was too wrapped up in his own issues. On a side note, if you're a Destiel (Dean/Cas) fan this episode is epic for long lingering looks and loaded statements. Even after the finale I am still hoping that Dean can get off of high horse and forgive Cas in time to save him.
Number 4: Ben and Lisa forget, but Dean remembers.
“Let it Bleed” (6.21)
The most recent moment on our list, but no less traumatic and considering the emotional trauma that was the final 2 episodes of season 6 that is saying something. I'm going to have to admit that I was never really a fan of Lisa, it's not that I don't think she's a nice person, it's just that I don't buy that they were in love each other. I mean sure she's attracted to him, who wouldn't be, and he clearly cares about her but it always seemed like both of them only loved the idea of each other. Lisa wants to remember her bad side and be there for the hero, and Dean wants the apple pie life, complete with wife and kid. But regardless of my feelings about their relationship this scene broke my heart. After thinking his relationship with them was over, Dean is forced back into Ben and Lisa's life in the most dramatic of terms. Kidnapped and held for ransom is probably not the best way to rekindle a relationship. We know it's over, Dean knows it's over but it's not that easy. Instead of just letting go of his lost relationship, Dean has Cas erase himself from Ben and Lisa's existence. I am not ashamed to admit that watching Dean's face as he looked and Ben and Lisa for the last time made me ball my eyes out. I'm talking floods of tears, and I can testify that Neffy was right there with me. The apple pie life that Dean had always wanted was so close and yet so far... oh man I'm gonna cry just thinking about it.
Number 3: Dean tearfully reveals all about hell.
“Heaven and Hell” (4.10)
Poor Dean, I mean really, poor poor Dean. It's like after season 1 the Supernatural creative team figured out that the more the broke Dean the better the show got, and this is one of those defining moments. After refusing to talk about hell for 10 episodes we finally find out why. It wasn't just that Dean remembered all of the horrific torture he'd had to endure or that it was 40 years not 4 months. It was that while Dean had lasted 30 years, he had eventually given in and begun to torture others. All Dean ever wanted to do was be the hero, and he already had enough issues of inadequacy so this is possibly the worst thing that could have happened to him. He wasn't at all comforted by Sam's insistence that 30 years was more then most people could have lasted, and it kind of makes all his angst over the fact that Castiel raised him from perdition a lot more understandable. This fantastic scene is topped of by the heartbreakingly quotable “I wish I couldn't feel a damn thing” complete with a fantastically gif worthy man tear that falls down his cheek as he says it making it one of the most memorable tearjerkers in Supernatural history.
Number 2: Sam dies, for the first time/Dean's mournful monologue.
“All Hell Breaks Loose Part 1” (2.21)/“All Hell Breaks Loose Part 2” (2.22)
Neffy: Nothing good comes from looking at Dean’s teary little face, just a pile full of snotty tissues. From now on it’s going to be a look that we see on a regular basis, but my god it doesn’t get any easier. In the finale of Season 2, Jake fatally wounds Sam and Dean runs over to cradle his little brother, pleading with him to make it through. “I’m going to take care of you. It’s my job, right, watch after my pain-in-the-ass little brother.” Cue Sam’s death (version 1), and a catastrophically sad speech by Dean as he sits over his little brother’s body. It’s now that we truly realise how lonely these boys are without each other, and that they are always going to resort to ridiculously dangerous means in order to stay side-by-side. Ridiculous decision number one being Dean’s subsequent deal with the crossroad’s demon that will keep us on the edge of our seats for the entirety of Season 3. But we can’t really blame them, can we?
UndieGirl: Can we blame them? Well we can a little bit, Dean's complete lack of self worth, which causes him to make that deal with the demon is the source of so many of the problems that happen after this. Sometimes I think that Dean's life would have been so much easier if he had just let Sam die, but then I think that we wouldn't have the next 4 seasons of awesome so I shut my mouth and get back to talking about the matter at hand. Sammy's death, and Dean's reaction. As shocked as I was when Jake stabbed Sam it was Dean's reaction that gets me. If his panic and begging at the scene of the crime weren't enough then Dean's speech to his brother's dead body should have you in some kind of catatonic state. It's only season 2 and it is still the best Dean breakdown, and it's no wonder. Dean was always the strong one, the together one, the big brother who could fix everything. This is the moment we realise just how vulnerable he really is, and that the reason he went to get Sam in that first episode (oh so long ago now) was that he doesn't know what to do without him. To this day, when I see Dean shed that one perfect tear and say “What am I supposed to do?” repeatedly to his little brother's dead body I still end up rocking on the floor in the foetal position wailing like a crazy person.
Number 1: Jo and Ellen go out with a bang.
“Abandon All Hope” (5.10)
Neffy: When the team head to Missouri to track down Lucifer, no one had any idea that they would end up losing so much. It also wasn’t until this moment that I realised how valuable Ellen and Jo were as characters. I’m generally pretty smug about that golden rule of Supernatural - no woman lasts longer than a single season - but for once, I had actually accepted that Jo was good enough for Dean (or at least good enough until he finds me). Never mind Lisa or Anna or the dozens of other women that Dean has hit up, I’ll always believe that he and Jo were meant to be. She proves herself at the start of the episode by turning down Dean’s formulaic advances, then does so again at the end by changing from a child to a self-sacrificing adult. So Jo hatches a plan to kill off the hellhounds and give the Winchester boys a final fighting chance against Lucifer, and Dean has to say goodbye. That final kiss, with the tenderness of both a brother and of a lover that could have been, is one of the most heart-shattering moments of television that I have ever seen.. I went to work in tears, unable to describe the genuine loss I felt towards my fictional friends. In fact, the entire episode was so cruelly effective that I’ve promised myself to never watch it again.
UndieGirl: When we first started talking about making this list, there was one moment that easily stood out from all the rest, and this was it. No question this is the single most heartbreaking moment of what it a really depressing television series. Like I have said before, there are just so many moments to choose from, but this one will always win. These characters, as with all female characters on this program, have always created controversy among the fanbase, but even if you hated them you cannot deny that their death is brutal. Not to mention the fact that they go out defending Sam and Dean, an act for which anyone would deserve glory. I found this all the more heartbreaking because I always like Jo and Ellen. Jo was cool, pretty and she could hold her own against Dean (anyone who can look into those beautiful eyes and say no deserves some sort of prize). And Ellen is the kind of person that I hope to be when I grow up – some might say that I am already fully grown but I say frick you. I can't actually describe much of this moment because I couldn't see a lot through the tears that were streaming down my face (and fogging up my glasses) and I refuse to watch it again, even I'm not that masochistic. All I remember was that it felt like I was losing members of my own family. I do not know what's more heartbreaking, that Jo died never having had sex with Dean or the fact that it was all for nothing. The Colt, really boys? You actually thought that would work. I love them both dearly but sometimes their stupidity upsets me. Jo and Ellen went out as they lived, together and strong till the last, and I would like thank them for giving some kudos to the underrepresented (and mostly awful) women of Supernatural.
I know I've said this before, but there really are so many other moments that could just have easily made this list. Although I'm not always the biggest Sam fan, when he has to shoot Madison, the first girl he loved since Jessica, it broke me a little bit (“Heart” 2.17). And any of the horrible Dean breakdowns could have counted – you have to admit there are a lot of them. When he tearfully calls his dad in “Home” (1.09), I wanted to jump into the television right then to hug him, and when he's wounded and broken in the hospital after his run in with Alistair and he tells Cas that he just can't do it, he can't save the world I almost can't handle it. But in the end we decided to go with the ones that had the most emotional impact while we were watching them for the first time.
You may disagree if you so choose, in fact I would actively encourage it. Please argue and comment to your hearts content.