Tear Jerker / Supernatural

♫ On a stormy sea of moving emotion
Tossed about, I'm like a ship on the ocean. ♫

— Kansas, "Carry On Wayward Son"

Make no mistake — The 'Verse of Supernatural is a textbook example of a Crapsack World, with the protagonists, their friends, their family, their allies, and even their enemies, along with pretty much anyone else they meet, being subjected to all kinds of torment, misery, and distress.

WARNING: Spoilers are unmarked.

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Season 1

1x01 - Pilot

• Baby!Sam's cry as Mary is burned by Yellow Eyes is very hard to watch.
• The look on Sam's face when he opens his eyes to see Jess on the ceiling for an instant, her stomach sliced open and her face still frozen with fear, before the room catches fire is even now one of the most painful moments in the show. It gets worse when he screams her name. This is the girl he loved that greeted him with a plate of cookies with a note telling him that she loved him and missed him when he'd only been gone a couple days.

1x03 - Dead In The Water

• Jake begging Peter to take him in exchange for his grandson Lucas.
• Peter kills Bill's children and is so heartbroken that he's Driven to Suicide.

1x05 - Bloody Mary

• The Reveal of why Mary has been stalking Charlie. Apparently, she and an abusive ex got into a pretty bad fight, culminating with Charlie breaking up with him and the boy stating that if she walked out on him, he would commit suicide. An enraged Charlie then told him to do it and left without looking back. Needless to say, her ex was a man of his word, and, well ...
  • For all her snark at the beginning of the episode, it's pretty clear that the secret has been weighing on her for some time now, even if the whole thing had never been her fault in the first place.

1x06 - Skin

• Just the concept of the entire episode. Your loved one comes home from a long day at work and you greet them happily, only to suddenly find yourself being beaten within an inch of your life. If the shapeshifter had left any of its victims alive, not only would it have soured their relationships forever, they would've left the abused party with a ton of PTSD and trauma as well.
  • Now think about it from the mimicked person's point of view. You've just arrived and the first thing you see is your mother or father or significant other all tied-up, covered in bruises and ropes. You try to help them escape, but they don't even want to be anywhere near you, let alone be touched by you. To make matters worse, how would you even begin to explain what had just happened to a medic or a police officer without making the whole thing sound as if the other person weren't losing their mind?
• Sam looking longingly at the picture of him, Becky, and Zach. Even though he's having fun spending time with Dean and getting back into "the family business," it's pretty obvious that Sam still misses his friends and his old life.
  • Sam's motivation to finish the case counts as well. Although he'd like nothing more than to keep his "normal" life separate from his past, Becky and Zach were his friends, and if he can keep them safe from the supernatural, even with great cost to their friendship, then so be it.
• Shapeshifter!Dean receiving Dean's memories and saying that as bad as the shapeshifter's background was, Dean's life and issues were a whole lot worse. Let that sink in.
  • In the same scene, the shapeshifter attacks Sam emotionally by tapping into Dean's thoughts, saying how Dean resented Sam for leaving and being selfish enough to live his own life when their father needed him. The way Sam's face just falls is heartbreaking enough on its own.
  • Afterwards, he outright threatens Becky to Sam's face, knowing fully well how close the two were in the past. A struggling Sam can only look on in horror as he realizes just how much danger he has brought onto his friend.
• When Shapeshifter!Dean is talking to Becky, she flippantly remarks how ridiculous the whole thing sounds, even calling the shapeshifter a 'genetic freak' to its face. The shapeshifter then gives a forced laugh before having this to say:
  Shapeshifter!Dean: So maybe this thing was born human, but was different. Hideous and hated. Until he learned to become someone else.
  • Later on, it adds:
  Shapeshifter!Dean: Funny. I kinda understand him. He's all alone. Close to no one. All it wants is for somebody to love him.
  • Granted, the thing had hurt dozens of people up until that point, so maybe it wasn't so sympathetic, but to hear its story from its point of view and to find out that it had been ostracized in the past for its appearance is still quite pitiful.
• Sam admitting that even at Stanford, he never quite felt as "normal" as he should.

1x09 - Home

• Dean's voice message to John:
  Dean: Dad? I know I've left you messages before. I don't even know if you'll get 'em. [clears his throat] But I'm with Sam. And we're in Lawrence. And there's somethin' in our old house. I don't know if it's the thing that killed Mom or not, but... [His voice breaks. He pauses, barely keeping himself together.] ... I don't know what to do. [He begins to cry.] So, whatever you're doin', if you could get here. Please. I need your help, Dad. [hangs up sadly, with tears in his eyes]
• One line which isn't really tear-jerking in itself but becomes so when you look at the situation now: "[John] doted on those kids."
• When Mary's spirit appears to her children, all she can say to Sam is "I'm sorry." When Sam, with tears in his eyes, asks for what exactly, all Mary can do is look at him sadly. Considering what we learn in season 4, it's retroactively heartbreaking.
  • Look at Dean's face when his mother appears. He can't keep his eyes off her, not even for one second. Even after all these years, after killing all those "ugly sons of bitches" and saving so many people, deep down, Dean Winchester still misses his mom.
• The Reveal that John has been watching over his boys all along, and that he wants to see them as badly as they want to see him.

1x12 - Faith

• In retrospect, after watching the Season 4 premiere and beyond, there is one line which is certain to make your heart hurt. Made even worse by the fact that Dean doesn't think that he should have been saved:
  Mrs. Rourke: [to Dean] Why do you deserve to live more than my daughter?
• The end of the episode, in which the boys are forced to stop a Reaper controlled by Grange's wife, though it will probably cost the tumor-in-the-brain Girl of the Week her life:
  Layla: I'm okay. Really. I guess if you're gonna have faith... you can't just have it when the miracles happen. You have to have it when they don't.
  • And:
    Dean: Well... I'm not much of the praying type... but... I'm gonna pray for you.
    Layla: [tearfully] Well... there's a miracle right there.
• Dean doesn't even run from the reaper when it comes after him.

1x13 - Route 666

• The episode is much-hated, but the description that Cassie's mother gives of the racist attacks (especially of the black church burning down with a children's choir inside) is heart-wrenching.
  • It's even worse due to being a case of Truth in Television; not only did these sorts of things really happen in the 1960s, they're still happening now.

1x15 - Nightmare

• Max Miller's entire life is a massive tearjerker. Much like Mary Winchester, Max's mother was burnt to a crisp on the ceiling when Max was a baby. Unlike John, who turned to hunting and killing as much demons as he could to deal with his grief, Mr. Miller began to blame Max for every single thing, along with beating him silly, sometimes with the help of his brother.
  • To make matters worse, his step-mother saw it happening and didn't even lift a single finger to help.
• Max revealing to Sam that even though he is now a young adult, his father still beats him bloody. When he lifts up his shirt to reveal the bruises, along with a couple of old scars, a visibly affected Sam can only wince and turn away.
  Sam: Look...what they did to you, what they all did to you growing up, they deserve to be punished—
  Max: [scoffs] Growing up? Ha, try last week. My dad still hits me. Just in places people wouldn't see it. Old habits die hard, I guess.
• Max committing suicide in the end. Even if one takes away the supernatural aspects of his story, he was still an abused kid who was most likely depressed from having lived such a hard life and saw no other way out.
  • Sam dealing with his guilt about the situation afterwards. Even though Dean tries to comfort him and say that he couldn't possibly have prevented any of it, Sam obviously still thinks that Max is yet another person who died on his watch.

1x21 - Salvation

• When Sam pins his anger on Dean for stopping him from following Azazel.
  Dean: [emotionally, as Sam pins him up against the wall] Sammy, look... the three of us—that's all we have. And that's all I have. Sometimes I feel like I'm barely holdin' it together, man.
  [Sam, with tears in his eyes, lets go of Dean.]
  Dean: Without you and Dad...
  [Sam turns away from Dean]
• John's old friends are being killed by demons and he finally snaps when Sam questions him one too many times:
  John: I want to stop losing people we love. I want you to go to school, I want Dean to have a home. I want... I want Mary alive. It's just... I just want this to be over.

1x22 - Devil's Trap

• After all of Sam and Dean's issues with John in the first season:
  Dean: Daddy, please...
• How Dean realizes that John is possessed by Azazel: he gave them praise for making it out alive, rather than chewing them out for using one of the Colt's few remaining bullets. It's John being a good person and a good father that tips him off. Make of that what you will.

Season 2

2x01 - In My Time of Dying

• The last ten minutes. John has a somewhat-heartwarming talk with a bedridden Dean, telling him to take care of Sam, then whispering something in Dean's ear before exiting the room, heading into another room, putting the Colt down, and saying "Okay." Sam then returns, finds his dad's lifeless body on the floor, and screams for help, all of this taking place without any dialogue heard. Doctors then work to revive John to no avail, all the while Dean and Sam watch helplessly.

2x04 - Children Shouldn't Play With Dead Things

• The episode's end:
  Dean: Sam... you and Dad—you're the most important people in my life. And now... I never should have come back, Sam. It wasn't natural. And now, look what's come of it. I was dead. And I should have stayed dead. [His voice breaks, his bottom lip quivers.] You wanted to know how I was feeling. Well, that's it.
  [Sam has tears in his eyes. He nods, understanding.]
  Dean: So, tell me... what could you possibly say to make that all right? [He looks at Sam, who can't say anything, as tears stream down his face. The two sit in silence as the screen fades to black.]

2x09 - Croatoan

• The part where Sam might have gotten infected by the virus. Basically this whole scene deserves examination for how it affects both brothers:
  • Sam is teary-eyed, and wants a gun so he can finish himself off before the virus affects him, and is aghast when Dean refuses to allow anyone to kill him despite his repeated begging that he do so before he can hurt anyone else.
  • Meanwhile Dean does the unthinkable and gives up his car so the others can escape, before just locking himself in with his (apparently) infected brother, essentially giving up rather than go on without the last remaining member of his family.

2x13 - Houses of the Holy

• Dean's entire Rage Against the Heavens speech, especially when you know that Mary was right and how much worse that makes everything...
  Sam: I don't know, Dean, I just... I wanted to believe, so badly. It's so damn hard to do this, what we do. All alone, you know? There's so much evil out there in the world, Dean, I feel like I could drown in it. And when I think about my destiny, when I think about how I could end up...
  Dean: Yeah, well, don't worry about that, alright? I'm watching out for you.
  Sam: Yeah, I know you are. But you're just one person, Dean. And I needed to think that there was something else watching too, you know? Some higher power. Some greater good. And that maybe...
  Dean: Maybe what?
  Sam: Maybe I could be saved.
  Dean: Okay, all right. You know what? I get it. You’ve got faith. Hey, good for you. I’m sure it makes things easier. I’ll tell you who else had faith like that –- Mom. She used to tell me when she’d tuck me in that angels were watching over us. In fact, that was the last thing she ever said to me.
  Sam: You never told me that.
  Dean: What’s to tell? She was wrong. There was nothing protecting her. There’s no higher power, there’s no God. There’s just chaos and violence and random, unpredictable evil that comes out of nowhere, and rips you to shreds. So, you want me to believe in this stuff? I’m gonna need to see some hard proof. You got any?

2x14 - Born Under A Bad Sign

• That bit where Sam begs Dean to kill him. And then Dean says, "I've tried so hard to keep you safe..."
  • Then he finally says that he would rather die.
• Jo really gets put through the wringer here. Sam mocks her one-sided feelings for Dean, nearly rapes her, knocks her out, ties her up, threatens to carve her up with a knife, forces to relive her dad's death in which John got Bill killed when he accidentally exposed them, claims that John actually shot him to end his suffering when he was holding his guts in his hands and praying to come home to see her and her mom one more time (described in graphic detail), she sees first-hand that her crush would prefer to let her die than save her from his brother, and he refuses to let her help him because he doesn't think she's good enough of a hunter to not get herself killed, even threatening to tie her up again if she didn't stay put.
  Dean: I'll call you. (leaves)
  Jo: (whispering) No, you won't.

2x15 - Tall Tales

• Knowing who the Trickster is in retrospect, that being the Archangel Gabriel, can be depressing when you consider his Backstory, as well as the fate that awaits him in Apocalypse World eleven years later.

2x16 - Roadkill

• The Reveal of poor Molly the ghost's true nature. This got a remake in the anime adaption, and is just as sad then.

2x17 - Heart

• The end, where Sam is forced to shoot Madison. The worst part is the way she hopelessly accepts her fate and tells Sam that she knows how hard he tried to cure her of being a werewolf and that he can save her by killing her. It gets worse when we later found out that she is the first woman that he has had strong feelings for ever since Jessica's death.

2x20 - What Is And What Should Never Be

• You can either: have your heart broken by Dean's godawful mental state, be slightly crushed by the Downer Ending (especially when you take "All Hell Breaks Loose" into account), feel the tears welling up at Dean meeting his Mom and being glad that (at least in this "reality") his father's death wasn't all his fault, need some happy pills after the revelation that Alt!Sam can't stand Dean or cry your heart out at the graveyard scene where Dean self-orders himself to go back to his normal, oh-so-very-crappy life. No matter which you choose, you're gonna need tissues.
  Fake!Sam: Why is it our job to save everyone? Haven't we done enough?
• The look on Dean's face when Alt!Sam asks "Since when did you start calling me 'Sammy'?" The whole conversation, actually...
• Dean's entire family seems to see him as a screw up, his brother hates him and he is burdened with the guilt of all of the people he never saved. And this is Dean's idea of a happy existence.

2x21 - All Hell Breaks Loose - Part 1

• Sam's death. Take the one thing that Dean couldn't stand to have happen, and it happened while he was standing right there. Watching Sam die in Dean's arms and seeing Dean finally lose it completely... And they say Joss Whedon is cruel to his characters.
  • Dean's plea for Sam not to die:
    Dean: Sam, Sam, Sam. Hey, hey... Come here, come here, let me look at you. Oh, hey look, hey look at me it's not even that bad. It's not even that bad, alright? Sammy, Sam! Hey, listen to me, we are going to patch you up, okay... You'll be as good as new. Huh? I'm going to take care of you. I'm going to take care of you. I gotcha. It's my job, right, watch out for my pain-in-the-ass little brother.... [realizes that Sam is dead] Sam... Sam.... Sam! Sammy! No.. no-n-n-n-n-no. Oh god... Oh god...SAM!

2x22 - All Hell Breaks Loose - Part 2

• Bobby tells Dean to man up, bury Sam and get on with helping him stop the end of the world. Dean's reply? "THEN LET IT END!"
• Dean is left alone with Sam's corpse... where, after a gut-wrenching speech, he goes and does the dumbest thing of his entire life...
  Dean: [to Sam's corpse] You know, when we were little, and you couldn't been more than five, you just started asking questions. "How come we didn't have a mom?" "Why do we always have to move around?" "Where'd Dad go when he'd take off for days at a time?" I remember I begged you, "Quit asking, Sammy. Man, you don't want to know." I just wanted you to be a kid... Just for a little while longer. I always tried to protect you... Keep you safe... Dad didn't even have to tell me. It was just always my responsibility, you know? It's like I had one job... I had one job... [voice breaking] And I screwed it up. I blew it. And for that, I'm sorry. [crying openly] I guess that's what I do. I let down the people I love. I let Dad down. And now I guess I'm just supposed to let you down, too. How can I? How am I supposed to live with that? What am I supposed to do? Sammy... God... [angry] What am I supposed to do? [inhales sharply; stands; screams] WHAT AM I SUPPOSED TO DO?! [cut to Dean speeding off in the Impala towards a crossroad...]
• Dean's just sold his soul and only has a year to live, but he begs Bobby not to tell Sam.
  • "Are you that screwed in the head?!" Yes, Bobby, yes he is.
• John crawling out of Hell to save his sons again. Then any composure is gone with the exchange:
  Sam: All this time, and I don't know what to say.
  Dean: I do. That was for our mom, you son of a bitch.
• The ending conversation just breaks Dean down completely. He's so vulnerable and childlike when he's begging Sam not to be mad at him and he looks genuinely shocked that Sam might actually want to save him. Poor, broken, stupid little boy.

Season 3

3x07 - Fresh Blood

• Dean teaches Sam how to fix the Impala, so that he'll know how to after Dean dies.
• Sam's argument with Dean, especially the end. "I wish you'd drop the show and be my brother again. 'Cos... Just 'cos."
• YMMV for some, but in the same episode, Gordon killing Kubrick. It's obvious that he really didn't want to do it.

3x08 - A Very Supernatural Christmas

• We find out where Dean got his amulet (Sam gave it to him when they were kids) and they both try their hardest to have a happy Christmas even knowing that next year, Dean will be dead. Made even worse if you read the scene as Dean only getting the amulet because Sam doesn't care about the gift any more since it can't go to John.

• The murders committed by the monster of the week (MOW) in this episode happened right in front of each victim's loved ones. The first victim was dressed as Santa so his grandson would believe he got a visit from St. Nicolas, only for him to be graphically dragged up the chimney and slaughtered while his grandson watched.^note To make things worse, this was a flashback to an event that happened on Christmas eve the year before, Which meant Stevie (the grandson) had to first, watch Santa be murdered before his very eyes on Christmas eve, then spend Christmas day finding out it was actually his grandpa who was killed and having to deal with that instead of opening presents. The second victim had to hear her father in the next room get dragged screaming up the chimney while he was in the middle of decorating the tree. Victim 3, Mr. Caldwell, was attacked in the dead of night, awoken from a sound sleep to be dragged away in a sack, struggling and screaming for help while his son Jimmy, who can't be any older than six or seven and thought he was getting an early visit from Santa, watches thinking Santa is doing this horrible thing to his family. And to make matters worse, these all happens within days of Christmas, which means a holiday that's supposed to be about love, joy and family is being spent in mourning and not feeling safe in their own homes. The only possible solace is if the person Sam and Dean found struggling in that sack in the MOW's basement was Jimmy Caldwell's father, then they were probably able to rescue him after killing the monsters of the week and reunite him with his family, giving at least Jimmy a hope for emotional recovery.

3x11 - Mystery Spot

• Sam's increasing desperation and terribly upset Puppy-Dog Eyes as the day repeats again and again, offset eerily by the Black Comedy of Dean's repeated, and often mundane, deaths.
• The sobbing, desperate Sam holding Dean's body in his arms when Dean dies on Wednesday, and Sam doesn't wake up.
  • In retrospect the Trickster bringing Dean back to life because he was bored is heartbreaking when you consider that in season five you discover that he is Gabriel and left Heaven because he couldn't stand to watch his family rip themselves apart, that he only wanted it all to be over. He would give anything for everything to be reversed so that his family was together again. Maybe he didn't just get bored of screwing with Sam...
  • Though vague and entirely coincidental, as that plot point wasn't even formulated at the time, when Sam tearfully says, "He's my brother," for a second the Trickster appears to be contemplating this line, as if he were remembering his life before and his then-nonexistent relationship with his brothers, and then goes on with a casual, "Yep."
  • For six months after Dean dies, Sam is basically an emotionless shell as he spends all his time trying to hunt down the Trickster, and killing a bunch of other monsters on the way. Then, when he finds the Trickster again, does he threaten him? Does he try to kill him once he reveals himself for real? No. He just pleads to be taken back to that last Wednesday before Dean died, all the while staring at him with those famous heartbroken puppy eyes.
• That ending shot of the Winchester boys finally leaving their motel room, and Sam giving one last look backwards, as if remembering how many times he woke up in there and had to watch his brother die.

3x12 - Jus in Bello

• The sudden Downer Ending, where Lilith shows up at the police station and slaughters everyone, including the virginal Nice Girl who was willing to sacrifice herself to stop the army of demons, not to mention Agent Henrikson.

3x13 - Ghostfacers

• When Corbett died.

3x14 - Long-Distance Caller

• The moments where Dean is so close to having a complete nervous breakdown where he was so desperate to believe that John would save him from Hell.

3x15 - Time Is On My Side

• Doc Benton is trapped underground and cries to be let out as Dean and Sam bury him. He feels more sorry for him than Bela, who dies in the end at the jaws of hellhounds, but not that she doesn't deserve some sympathy. Part of it is simply because, unlike Sam and Dean, the only way Bela is getting out of Hell is by eventually losing all her humanity and sense of self through horrible, unending torture and becoming a monstrous abomination that will never truly find peace or salvation, all because the desperate, broken teenager she used to be wanted her parents to stop hurting her. The other part is an exchange she has with Dean, because it shows that Bela is so screwed up that she doesn't understand that just maybe someone would just help someone else purely out of the goodness of their heart. (*sniff*)
  Bela: [breaking down into tears] Dean, listen, I need help.
  Dean: Sweetheart, we are weeks past help!
  Bela: I know I don't deserve it.
  Dean: You know what? You're right, you don't. But you know what the bitch of the bunch is? If you would have just come to us sooner and asked for help we probably could have taken the Colt and saved you!
  Bela: [still crying] I know, and saved yourself.

3x16 - No Rest for the Wicked

• Dean is torn apart by a Hellhound in front of Sam's eyes, right after convincing Sam not to use his powers to save him. Sam cradles his body, crying, while Dean screams for his brother in Hell.
  Sam: Then what am I supposed to do?
  Dean: Keep fighting. Take care of my wheels. Sam, remember what Dad taught you. Remember what I taught you.
  • Here's a "fun" exercise; after seeing "No Rest for the Wicked", try watching the middle of "A Very Supernatural Christmas" ("I don't get it. You haven't talked about Christmas for years." "Well, yeah. But this is my last year." "I know. That's why I can't." "What do you mean?" "I mean, I can't sit around drinking eggnog, celebrating Christmas, when I know next year, you'll be dead. I just can't." And then they just sit on their different beds, silent and alone and depressed) and the end (where they drink eggnog, celebrate Christmas, and watch a football game) without bawling.
  • Speaking of things that hurt far more through Hell-tinted glasses, how about the end of "Fresh Blood" where Dean acts like a brother again and shows Sam how to fix the Impala.
  • Another Hell-tinted glasses one: The recap at the beginning of "No Rest For The Wicked". The last few shots play out like a preemptive Really Dead Montage. especially that last shot of Dean leaning against the car with a little half-smile, looking, for Dean, unusually innocent. It looks like the sort of thing you'd display at a funeral.

Season 4

4x01 - Lazarus Rising

• Sam explains what he did after Dean died:
  Sam: (furiously) I tried everything, that's the truth. I tried opening the Devil's Gate, hell, I tried bargaining, Dean, but no demon would deal, all right? You were rotting in Hell for months—for months!—and I couldn't stop it. So I'm sorry I wasn't the one who broke you out. (starting to break down) Dean, I'm sorry.
• It might be true that the writers rely a bit too much on Dean's self-esteem to bring out good angst but there's this little exchange:
  Castiel: Good things do happen, Dean.
  Dean: (looking like he's about to crack) Not in my experience.
  Castiel: What's the matter? (slowly realizing) You don't think you deserve to be saved.
  Dean: (completely changing the subject and after a long pause) Why'd you do it?

4x02 - Are You There, God? It's Me, Dean Winchester

• There's the real Meg Masters' speech to Dean about her year-long possession, subsequent (and entirely preventable) death, and her little sister's suicide.
  Meg: You're supposed to help people, Dean, why didn't you help me?

4x03 - In The Beginning

• The episode was filled to the brim with these. Take your pick: you can have the horrible Dramatic Irony of seeing John Winchester as a young, innocent himbo when you know how he ends up, you can have Dean almost in tears when his pre-burned mother tells him how she doesn't want her children to grow up in her hunter lifestyle and then him begging her to stay in bed the night she died, you can have Dean too tired and exhausted to choose all the people he's saved over his family this time or the almost crushing realization that the Winchesters were doomed from the start and that Dean is somewhat to blame for that. Somebody want to give the poor boy a hug?
• In particular, Dean bonds with Mary, which is all the more heartbreaking when he knows she will one day die. Knowing he won't be successful, he tries to warn her:

  Dean: On November 2, 1983, don't get out of bed. No matter what you hear, or what you see. Promise me you won't get out of bed.

4x04 - Metamorphosis

• When Dean finds out that Sam is using his powers he basically says that he is just as bad as the things they hunt and assaults him for using his powers. It's especially painful because this hits Sam's fear of being evil that goes all the way back to Season 2. Oh, Dean.
• The premise of the episode. An innocent man is viciously overriden by his monster genes, so that he eats other humans. The efforts which the man makes to save his humanity, all amounted for nothing as he becomes a monster to save his wife, only for his wife to (rightfully) disown him, cementing his path to evil. The pain is evident in Sam as well as he is forced to Mercy Kill the husband. It kinda shatters poor Sam's beliefs. Harsher in Hindsight when you compare the monster husband to what Sam becomes in the final 3 episodes of this season...

4x05 - Monster Movie

• Shapeshifters tend to have tear-jerky elements to them to begin with, mostly due to their natural state being so hideous that even their own parents try to kill them. But this one really takes the cake. The first shapeshifter Sam and Dean encountered was a vicious sadist who delighted in torturing his victims to death under the guise of their loved ones. This one grew up being called a monster, and when he first saw monster movies, he was shocked that creatures given the same label as him were regarded not with disgust, but with fear and even respect. If he was forced to be a monster, he wanted to be that kind of monster. And when he's dying, his final words are
  Fake!Dracula: Perhaps this is how the movie should end.

4x06 - Yellow Fever

• Definitely doubles as nightmare fuel, but there's just something about the normally wise-cracking, tough guy Dean just sitting in a hotel room waiting, psychotic and absolutely terrified, that's simply gut-wrenching...
• The book mocking Dean ("You're dying... again... loser." "Baby gonna cry?").
• Poor Luther Garland. If it wasn't enough he was ostracized for being big and mean-looking despite being gentle and kind, the only person who ever showed him kindness went missing before committing suicide. And to add to the trauma, when her husband thinks Luther had something to do with it, he kills the innocent man in perhaps the most horrific and painful way possible.

4x09 - I Know What You Did Last Summer

• Sam's flashbacks revealing just how much of a mess he was after Dean's death.

4x10 - Heaven and Hell

• Dean's breakdown in the final scene is one of the most powerful scenes in the entire show. Dean reveals that his four months in Hell was actually 40 years for him, and that he was tortured in unspeakable ways every day. And at the end of every day, he was offered to be left off the rack in exchange for taking up the torture himself. Jensen Ackles' voice is dead, as if he's trying so damn hard to keep himself from breaking down, then when Dean says that he told the demons to "stick it where the sun shines," the pride in his voice gives you hope that he never broke, THEN he says "for thirty years." And you know what that means. Then Ackles lets the emotion come through in his voice as Dean fully voices the horror and shame that he has been hiding all season, talking about the souls that he tortured for a decade. By the end, Dean admits that he feels empty inside and wishes that he couldn't feel anything.

4x12 - Criss Angel Is A Douchebag

• The final line from Jay: "Throw them away."
• Jay's entire speech at the end counts as this.

4x13 - After School Special

• We get flashbacks to Sam's school life, where he protects a friend of his from a bully with his Hunter training, in a scene that every bullied kid secretly wished they could do. Then, cut to present day, where we learn that Dirk, the kid doing the bullying, had gone through seeing his mother die from cancer before the events had taken place, and was most likely venting his anger. We get a speech from his father about how caring he had been to his mother, and that her death, and the subsequent bullying for being poor and the nickname "Dirk the Jerk" (which Sam dubbed him after kicking his ass) drove him to drugs and alcohol, causing him to overdose and die five years later and cause his vengeful spirit to possess bullied kids and get them to fight back. The entire scene is held together by Jared's expressions, not realizing that Dirk had had such a hard life, and had inadvertently contributed to his death. You can see the pain on his face in the scene.
• The whole reason Sam and Dean are there in the first place: A girl named Taylor is being called a slut in the cafeteria and is denied her usual spot at what seems to be the "cool kids" table. She goes and sits down, whereupon another student tries to make her feel better, only to get called a "fat pig" by Taylor for her trouble. This was a nasty thing to say for sure, but Taylor didn't really mean it and gets murdered by the girl while trying to apologize. Even worse because the girl was possessed and clearly would not have murdered Taylor in her normal state.
• As if this whole episode needed to drive the "bullying is wrong" lesson home, we enter Barry. He was the picturesque high school nerd and suffered dearly for it. Apart from the fact that his parents were divorced, his school life didn't help and the kid was deeply depressed, so much so that he was on "every anti-psychotic in the book." The only time he seemed to be happy was when Sam arrived, and it's likely that Sam was Barry's only friend. Unfortunately, Sam's stay at the high school wasn't long, and so Barry was left alone again. A year later, he slit his wrists in the girls' bathroom. Sam laments the fact that had he been allowed to stay at the school longer, maybe his friend wouldn't have been Driven to Suicide.
  • The ending flashback to Young!Sam leaving the school. Dean gets in the car without a backward glance, but Sam looks back and waves at Barry, who watches silently from a window. We already know Barry will be dead in a few weeks.
  • The teacher asking Sam if he's happy. Sam doesn't answer, but you can once again see the pain on his face.

4x14 - Sex and Violence

• The brothers exchanging hurtful words and even when they say everything's cool between them, it's not.

4x15 - Death Takes A Holiday

• Pamela slowly dying at the end of the episode. Her voice breaks when she tells the guilt-ridden Winchester boys, "I told you I didn't want anything to do with this!"

4x16 - On The Head Of A Pin

• Uriel turns out to be a traitor and has to be killed.
• Dean breaks completely (this is the end of the Hell-revelations, right, writers? Right?) after learning that John apparently never broke during his time in Hell, that he himself was the first of the 66 Seals to be broken, and that he's the only one who can stop the Apocalypse. Re-watch this scene knowing he was never intended to stop the Apocalypse, only to raze the world stopping Lucifer as Michael's vessel.

4x19 - Jump the Shark

• Sam getting to play big brother for a change. Dean refusing to believe it, then his face when he learns that John took Adam to a baseball game. Dean trying to protect him, because what the hell else does Dean Winchester do but protect his little brother, and Sam saying, "He's a Winchester. He's already cursed."

4x20 - The Rapture

• The episode, from beginning to end, is a masterpiece, especially from Misha Collins.
  • Claire asking Jimmy if he is going to say grace at the dinner table, and he answers, just barely keeping from bursting into tears, "I don't think I will."
  • The ending, when Jimmy demands that Castiel take him as his vessel again and release his daughter Claire, rather than letting him die and go to Heaven ("It doesn't matter. You take me. You take me."). Once Cas is back in Jimmy, he simply gets up, exchanges one look with Jimmy's wife, and continues to walk away.
  • Poor Amelia, who will never be able to share that thing that both Jimmy and Claire have. Even ignoring that she's probably never going to see her husband again, and oh yeah — all that therapy from being possessed by a demon, while her husband and daughter were the vessels of angels.
  • Jimmy's speech to the sky, demanding Castiel answer him and save his family because the angel promised. By the third line, he's not demanding; he's begging. The desperation in his voice is palpable, then there's the bitterness in his voice when Castiel doesn't show up. Made even worse by the fact that Castiel can probably hear him, but can't respond because he's being punished in Heaven for disobeying.
  • All of these things become so much more heartbreaking after watching "The Things We Left Behind" and "Angel Heart" where we see what exactly happened to Jimmy's family; Amelia ended up leaving Claire with her grandmother and go out to "find herself", where she ends up being taken prisoner and having her soul fed upon for years by an angel, eventually dying, while Claire grows up to be a teenage runaway living out on the streets, in and out of juvenile facilities due to both her parents being missing. To top it off, Castiel finally confirms that Jimmy is in fact dead after Cas was obliterated by Raphael, removing any hope once and for all that once his mission is over Jimmy could go back to living a normal, everyday life.

4x21 - When the Levee Breaks

• Everything about the episode, but especially Dean calling Sam a monster. The last three shots of the episode (Sam walks out after beating the holy living shit out of Dean, and Dean is so devastated and hurt that he can't even roll over onto his side to get up) were particularly heart-wrenching.
• The looks on both Castiel and Anna's faces when he is forced to betray her by turning her over to other angels.

4x22 - Lucifer Rising

• That goddamned voicemail. Dean calls Sam and leaves him a message telling him that he forgives him and they're still family, no matter what. By the time Sam listens to it, unsure as to whether or not he should go ahead with Ruby's plan, it's been altered so that "Dean" calls him a blood-sucking freak and says he's done trying to save him and there's no going back, which pushes Sam into trying to stop the Apocalypse by killing Lilith (which he seems to expect to die doing), accidentally causing the Apocalypse instead. And it looks like no one in-universe ever realized the voicemail swap, so to this day Dean might think that Sam just didn't care and Sam might think that Dean just gave up on him.
• Ruby, and everything that happens to her.
  • It turns out she's been struggling for the past two years to help save her people, she's sacrificed everything and made herself an outcast to do it; she's so proud of Sam for (as she sees it) becoming their savior and she loves him so completely for that, and right when she's finally won after fighting so damn hard - it all falls apart on her. Sure, her goals weren't great for humanity, but most freaking tragic character yet?
  • Demons in particular are ridiculously tragic if you think about it. Sure, they're sick, evil bastards now, but they were once human, people, with a life, a personality, loved ones, etc. Most of them were probably decent people, seeing as how it only takes a wish, a deal, and a kiss with a stranger to send your soul to Hell. They've been tortured for centuries (in Earth time) until they lost their memories of their human lives and turned into these evil beings that take their anger and pain out on everybody and everything else. Lucifer, the god they worship and look to in the hopes that he'll lead them all to Paradise, secretly despises them and plans to kill them all once he's through using them as tools. When they're killed, they don't go to Heaven to find peace or happiness, they just stop being completely (which may or may not be a blessing in disguise for their sake as well as everyone else's). C'mon, guys, demons are the crowning example of a Jerkass Woobie!
  • Ruby's look of shock when Sam grabs her to help Dean kill her — before she gets caught up in the pain of Dean literally twisting the knife in the wound before killing her — can be sad in its own right, but so many fans hate her that her death was generally seen as more awesome than anything else. However, the way Sam winces◊ when Dean slams her knife into her and the blink-and-you-miss-it look of intense PAIN◊ on Sam's face as she's dying, like he's fighting the impulse to cry, are more straightforward examples if you notice them. In that moment you realize that Sam did love Ruby as much as she loved him, even after he learned that she was a double-agent, and that he had to force himself to help Dean kill her. He couldn't even emote about it in later episodes because there was too much tension with him and Dean, and Dean hated her too much to give him sympathy, so Sam had to cope with this massive trauma completely on his own, which he hadn't had to do with anyone else he had previously loved and lost. A hunter and a demon, in love but still believing they have to betray each other for the greater good... tragic.

Season 5

5x01 - Sympathy for the Devil

• Bobby's horror and disgust when Sam reveals that it was his own fault the Apocalypse began. Sam looks so hurt and miserable as Bobby tells him to lose his number—if they even survive this. To make matters worse, Dean just stands there, shoulders tensed and eyes narrowed, and doesn't say a word. It turns out that Bobby is possessed at the time, but it still stings. Bobby later reveals that he was awake at the time the demon spoke, so that couldn't have been easy on him, either.

5x02 - Good God, Y'all

• The brothers splitting up , full stop. Even when they fight, they're still all the family they have, and seeing them separate is so very wrong.

5x03 - Free To Be You and Me

• Sam and "Jess", AKA Lucifer,'s scenes together. Four years later, and he can still say, "I miss you so much," and mean it. It's even worse when she starts to tell him matter-of-factly that it is his fault she died.
• Also, when Dean and Castiel run out of the brothel that Cas got them kicked out of and Dean just starts laughing so hard and says "I haven't laughed like that in... in years." And then his smile slowly dies as that statement sinks in.

5x04 - The End

• The whole thing, but somehow Castiel was the worst, especially his line "I'm hapless, I'm hopeless—I mean, why the hell not bury myself in women and decadence, right? It's the end, baby." Quite depressing. Future!Dean is ready to sacrifice him (and the other guys, but present!Dean was most horrified when it came to Castiel) without batting an eyelash. And it was entirely pointless. Dean and Castiel's reunion at the end of the episode was a Heartwarming Moment, but also a Tear Jerker.
  '''Present!Dean: You're going to feed your friends into a meat grinder? Cas, too?
• What makes it even sadder is knowing that Future!Dean's mission as doomed from the start. Their last hope, the Colt, was completely useless. Even if future!Dean had gotten to Lucifer and shot him, the Colt can't kill Lucifer (along with Michael, God, Death and two others). Their one chance to beat the Devil was already gone, because Sam was the only one who could really fight him, and his (lost) relationship with Dean was the only thing that could have given him the strength to win.
• Future!Dean begging Present!Dean to say "yes" to Michael, saying that the angels have given up and left, that he knows now that he was wrong to not say "yes", and that they've already basically lost. The Deans stare at each other for awhile before Future!Dean bitterly realizes that it'll all still happen anyway. ("But you won't. 'Cause I didn't. Because that's just not us, is it?") It's... hard to watch Future!Dean, but it's hard not to feel sorry for him.
• Dean standing with Lucifer (who's wearing Sam's form) in the rainy garden. Dean is trembling, visibly fighting back tears, but he still refuses to back down.

5x08 - Changing Channels

• It was a funny episode, but Gabriel revealing that he left Heaven because he couldn't stand by and watch his family fight was a bit painful. When he's standing all alone in the middle of the circle as the fire begins to go out, soaking wet, he just looked so isolated and lonely.
• The painful Mood Whiplash of Dean being asked if John and Mary would still be alive if Sam was never born. He says "Yes," and has no idea what he's actually saying.

5x10 - Abandon All Hope...

• Jo, dying from her wounds, offers to commit suicide by blowing herself up along with the hellhounds just outside so that Dean and Sam can have a shot at ganking Lucifer. Ellen stays behind with her daughter to rig the explosives and open the doors. Dean gives Jo a goodbye kiss, and he and Sam escape out the back. Jo dies right next to her mother before she can trigger the bomb, so Ellen hits the button and blows up the shop. It was a beautiful send-off for two deserving characters, but it was all so pointless...
  Ellen: (sobbing) It's okay... it's okay. (kisses the top of her daughter's head) That's my good girl.
  • Jo tries not to break down in front of her mom and friends, up until Dean kisses her forehead—then her face just crumples and you can see how scared and upset she is when she realizes that her life really is over. Dean kisses her goodbye, and his expression collapses into despair for a moment before he pulls away—losing friends never gets easier.
  • When Ellen announces she's not leaving her to die alone, Jo tries to argue with her, audibly choked-up and on the verge of tears, but the fact that her mom's going to be there for her to the end is clearly a relief for the poor girl.
  • The fact that Jo dies in Ellen's arms makes this scene even worse. No mother should have to watch her daughter die.
  • Even more heartbreaking when you know that Ellen's parting words to Dean—"Kick it in the ass. Don't miss"—were a Shout-Out to producer Kim Manners, who passed away in early 2009.
  • Seriously, Jo and Ellen's deaths are seen as one of the saddest moments of the show, if not the saddest. It even got the Television Without Pity recapper at the time, Damien, to completely drop all snide remarks and instead give a serious summary of just that part of the episode—something he only ever did for this particular episode for this particular moment. Repeat, it made Television Without Pity lose the snark.
  • Dean and Sam are speechless and tearful through the whole scene, staring at Jo and Ellen and then back at the exploded hardware store in open-mouthed shock and grief.

5x13 - The Song Remains the Same

• When the boys discover the people their parents really were. John indirectly yelling at himself for what he put the boys through was bad enough, but then you have Mary crying when she learns Sam and Dean became hunters...
  • When they first show up at John and Mary's house Dean goes straight into the standard Winchester lying-to-strangers patter, but Sam takes one look at his parents and practically bursts into involuntary tears right there on their doorstep. He's barely able to speak for the rest of the scene. Special mention is his face when he sees Mary opening the door, as he barely has any memory of her, if any.
  • When Sam and Dean try to convince Mary to leave John to prevent themselves from being born. They're basically attempting to commit cosmic suicide together to save their mother's life and (maybe) avert the apocalypse.

5x14 - My Bloody Valentine

• The final scene of the episode is one of the saddest moments in Supernatural. Leading up to it we find out why Dean is immune to Famine. Because he is "dead inside", he wants nothing because he is broken and defeated. Later on while Sam is once again detoxing from demon blood, Dean goes outside and sits down. Then he proceeds to cry, not just a single tear but full on crying, and looks up at the sky, begging for "some help."

5x15 - Dead Men Don't Wear PlaidBobby, when he has to kill his zombified wife. Heartbreaking because of real-life: Jim Beaver is in fact a widower.

Bobby: She was the love of my life. How many times do I have to kill her?

5x16 - Dark Side of the Moon

• The boys die and go to Heaven where they know the angels will bring them back to life so they can do their parts for the apocalypse, so you'd think nothing could be angsty about temporary Heaven, right? WRONG!
  • All of Sam's favorite memories are times when he abandoned his family and got to play at 'being normal.' Dean's reaction when he realizes this is gut-wrenching. And it only becomes even more heart-breaking when you realize that both of Dean's favorite memories were not even moments when he was particularly happy, but rather moments when he was making his family happy.
  Dean: This is your idea of heaven? Wow... this was one of the worst nights of my life.
  • Dean's face when his mom starts telling him how worthless he is and how much she hates him. Even knowing that she wasn't—couldn't possibly be—his real mom.
  • And the bit at the end, in which Castiel loses his last tiny shred of hope and faith onscreen. 'Maybe... maybe Joshua was lying?'
  • Or the moment right after, when Castiel completely breaks and rages at God.
  • In the very beginning after Sam is shot by angry hunters. The way the hunters just "know" that Dean will in fact kill them now. The fierce look on Dean's face is heartwrenching.
  Hunter: You just snuffed his brother. Do you really want Dean Winchester on your ass for the rest of your life?
  • Dean, not realizing he is dead and in heaven, follows a young Sam to a field where he relives a memory of taking Sam to shoot off fireworks on the 4th of July. Young Sam is delighted, and Dean looks the happiest we've seen him in a long time. All while "Knocking on Heaven's Door" plays in the background. The moment is then broken by gunshots as Dean remembers his violent death, and then finds himself alone in the dark field.
  • The ending. After an hour's worth of pain and angst (in Heaven, of all places), Dean trashing the amulet is still a tearjerker. Not only because of what it symbolized for the characters, but also because Dean waited until Sam was watching to do it, and because of Sam's reaction to it.
• It's the events of this episode that lead to Dean's suicidal spiral in 99 Problems and Point of No Return. Realizing that Sam's happiest memories are the ones without Dean or any of his family drives Dean over the edge into despair.

5x17 - 99 Problems

• Castiel's shock and grief once he learns that God knows what's happening—He just doesn't care. Castiel doesn't even cry or raise his voice; just stares into space and self-medicates whenever possible.

5x19 - Hammer of the Gods

• When Lucifer killed Gabriel/The Trickster with his own angel sword. And Team Free Will lost yet another ally.
• Kali's speech. "We were here first."
• Lucifer's reaction to killing his brother was a bit heart-wrenching, in a sympathy-for-the-devil kind of way.
• The pure wrenching look of heartbreak and terror on Gabriel's face when he realized what Lucifer had done, especially because we got faked out earlier in the episode when it seemed that Kali killed him, but he came back—only to get Killed Off for Real by his brother. Gabriel not only died at the hands of his brother, with his own sword, but told them how to beat Lucifer, but they never really liked him that much so won't really grieve for him that much. Combine that with the fact that most of his family probably either took him for dead anyway or just didn't care. He died a hero, saving the Winchesters, followed his father's orders, and indirectly saved the world by telling them how to seal Lucifer back up. And no one will ever know nor care about it. Redemption Equals Death, indeed.

5x22 - Swan Song

• The five year montage especially.
  Dean: Sammy, it's okay... it's okay, I'm here... I'm here... I'm not gonna leave you...
• Chuck's narration brought her to tears. In particular: "It never occurred to them that, sure, maybe they never really had a roof and four walls but they were never, in fact, homeless."
• A minor moment, but Bobby telling Sam to fight as hard as he could and Sam responding with "yes, sir", since it seemed to be Sam acknowledging that Bobby was a father to him (because he and Dean always called John "sir" as well).
• When Dean decides to go and see the fight between Sam/Lucifer and Adam/Michael to see if can help them despite Castiel's protests.
  Castiel: I want you to understand. The only thing your gonna see out there is Michael killing your brother
  Dean: Well, then I ain't gonna let him die alone.
• The looks on Lucifer and Michael's (especially Michael's) face when they know they are about to have to kill their own brother. Jake Abel masterfully portrays Michael in that scene, especially when his visibly hardens himself against Lucifer’s pleas. He’s just as sad as Lucifer, but he is a soldier first and he has a duty to his father.
• Watching Sam fall into the Cage, knowingly damning himself for eternity to save the world. One can only watch and weep at this act of utter and selfless heroism from a man the Angels once called an "abomination".
• Dean, after Sammy jumps into Hell and pulls Adam/Michael down with him, sitting in the cemetery utterly alone and realizing that he's lost everything.
• At the end, when a broken, tearful Dean goes to Lisa to fulfill his promise with Sam. His wobbly voice is what really sells it—he's like a little kid who's trying to be brave and not cry.
  Lisa: Are you alright?
  Dean: Yeah. Uh, if it's not too late, I... think I'd like to take you up on that beer.
  Lisa: It's never too late. It's okay. It's gonna be okay.
  [Lisa hugs Dean.]

Season 6

6x11 - Appointment In Samarra

• Sam tries to kill Bobby because he doesn't want his soul back, and tells Bobby that he knows that Dean doesn't care about him, only the version of his little brother who's still trapped in Hell. Even more so when you realize that he is afraid of the damage that Hell has wrought on his soul for being there for 180 years. Castiel stated that integrating his soul back into him could only lead to disaster.
• Dean is Death for the day as part of a wager to have Death save Sam's soul from hell. Dean attempts to do the right thing and spare a 12 year old girl with a serious heart condition who was fated to die. As a result, Jolene the nurse who was caring for her died decades before her time. Tessa explains that Dean caused her death by trying to defy the natural order. Jolene's widower husband ends up drunk driving and nearly causes the deaths of dozens of innocents. Dean has to take the ring off and lose the bet and ends up having to take the 12 year old girl to fix his mistake, leaving behind her father who, according to Tessa, doesn't really have any family left.

6X14 - Manniquin 3: The Reckoning

• Ben calls Dean for help. Dean rushes back to learn that Lisa is going on her fourth date. Dean goes to talk to Ben, who asks why doesn't he just come back and say he's sorry, then asks if it's because of something he or his mom did. Dean cuts him off and says he's leaving because he doesn't want to ruin their lives. Ben asks if it's because Dean's afraid something might follow him home. Dean explains that it has more to do with that fact that his life as a hunter makes him someone who just can't settle down with a family. Ben calls him out on it.
  Ben: You're a liar, Dean.
  Dean: Excuse me?!
  Ben: You say family's so important to you. Well, what do you call someone who loves you even when you're a dick? You know you're walking out on your family, right?
  [Dean response with silence while fighting back tears. Ben resumes playing his game in anger.]

6x15 - The French Mistake

• On a lighter (?) note, Misha actually being killed, complete with tearful and terrified begging for his life. And then pretty much everybody else.
• Sam doesn't want to stay in an alternate dimension where he has a wife who loves him, a secure high paying job, and where he is generally happy living a good life, because him and Dean aren't brothers and aren't talking in this alternate dimension. It's even more powerful when you see how shocked Dean is by Sam's response and how he tries to cover it up as if it doesn't faze him. It gets worse if you know anything about Real Life!Jared and Jensen's relationship. Basically, Real Life!Jared's reaction would pretty much be like Sam's, just to give you an idea...

6x16 - ...And Then There Were None

• Rufus' funeral. But averted with Samuel's death, since he was an asshole.

6x17 - My Heart Will Go On

• The ending, and the boys deciding not to tell Bobby about the alternate timeline where he was married to a still-living Ellen and happy.

6x20 - The Man Who Would Be King

• Castiel spends the whole episode praying to God, explaining how he came to work with Crowley in order to defeat Raphael and prevent a second attempt at the Apocalypse, and how he's come to both doubt himself and fear what he's turning into. At the end of the episode, Cas breaks down, on the verge of tears, begging his father to give him a sign that what he's doing is right. None seems to be forthcoming.
• For the whole episode, Dean has desperately clung to his faith in Castiel, when Bobby and Sam already stopped trusting him. Then Dean confronts him and asks him to look him in the eyes and tell him he's not working with Crowley: Castiel lowers his gaze without a word, and you can see Dean's last speck of faith go out from his eyes.

6x21 - Let It Bleed

• The entire conversation between Dean and Cas when Cas saves Dean from a demon and then asks for his trust is just unbelievably gut-wrenching. You don't even have to ship them (although it helps) for it to be powerful; either way it's still a terrible break between two individuals with strong feelings between them. Just their teary-eyed◊, emotional◊ facial expressions will pretty much just punch your heart in the balls.
• Take your pick of pretty much any scene with Dean and the Braedens in this episode: there's a terrified Ben begging a helpless Dean what to do as demons break in, kidnap his mom, and kill her new boyfriend, possessed Lisa taunting Dean and Ben before fatally stabbing herself in front of them as Dean exorcises her, Dean treating Ben like how his father treated him, Lisa is dying and Ben now hates Dean, and finally Dean apologizing to both of them despite neither of them have any idea who he really is because their memories have been wiped by Castiel at his request to protect them, ripping Dean's new family out of his life without any possibility of reconciliation. Goddammit.

6x22 - The Man Who Knew Too Much

• Castiel kills Balthazar, who's been trying to help the Winchesters. A Tear Jerker because he's not only killing his closest brother, but because Balthazar was doing something because he actually has a streak of decency, despite what he claimed in the previous episode.
  • And what makes it worse is that Balthazar's last word is "Cas...", in what was either shock or a plea, or a combination of both. And something in his eyes (possibly his grace leaving) looks just like tears. Heartbreaking.
  • While we're on that topic...
  Balthazar: Well, you'll always have little old me.
  Castiel: [stabs Balthazar] Yes, I'll always have you.
• Bobby's upset when the creature from Purgatory, also known as Eleanor Visyak, dies. She was killed by Castiel for her blood, but had also been trying to stop Purgatory from being opened because she isn't evil and likes this world. She dated Bobby and honestly cares about him. Bobby's anger at Castiel provokes tears.
• For fans of Castiel, his revelation in this episode that he's become God and is ready to kill anyone who doesn't follow him must have been a real blow to his diehard fans. Castiel, who was learning sarcasm, tips into the deep end, becoming the thing he was against.
  • It was mainly a tearjerker because a lot of Cas fans saw something heading towards him snapping. The continuous poor treatment he endured from all the other characters was brushed off by many other fans as Cas fans being too sensitive and that Cas didn't seem all that bothered by it. You really get the feeling had the Winchesters actually treated him a bit better, Dean's last-ditch "we're family, please stop" speech might have worked, rather than being laughably too little too late and insincere at that point.
• Tortured!Sam begging Normal!Sam to stay comatose rather than take the memories of Sam's time in Hell, and then handing him the knife to kill him when Normal!Sam refuses for Dean's sake.
  Sam: I can't leave my brother out there alone.

Season 7

7x01 - Meet the New Boss

• In the premiere, Castiel seemingly dies while returning the souls he took to Purgatory. Of course, he returns... possessed by Leviathans. Dean's reaction to losing his friend is both subtle and heart-wrenching.
  Dean: Cas, you child... why didn't you listen to me?
  • The look on Dean and Castiel's faces when, after everything they've been through together, Dean summons Death and demands that he kill Castiel. It gets worse when Castiel breaks Death's bonds, knowing that there is a good chance Bobby, Sam, and Dean will be slaughtered shortly thereafter.
  • Not to mention when Cas is seemingly dead, Dean and Bobby are checking and note that he's cold and has no pulse.
  Dean: Maybe angels don't need to breathe.
  Bobby: He's gone, Dean.
  • It's the wistful, desperate tone of Dean's voice and Bobby trying to break it to him gently that really brings the tears. And the following Mood Whiplash.
  • There's something extraordinarily painful about seeing Cas, who was so powerful and proud just minutes of episode-time before, slumped against that cabinet, covered in blood and suddenly too ill to even stand. Despite all the crap he pulled, he's still sympathetic enough that seeing him burn out hard like that hurts.

7x02 - Hello, Cruel World

• Dean picking up Castiel's trenchcoat.
• Even with everything going on, from the Leviathans to Sam's hallucinations, Bobby takes the time to ask how Dean's doing. Dean brushes it off, of course, but Bobby assures him that when he's ready to talk, he'll be there ("Where I always am"). Made even more heartbreaking because at the end of the episode, he's not there.

7x04 - Defending Your Life

• The last scene with Jo. The look on Dean and Jo's faces throughout the entire thing just break your heart, especially when she touches his cheek before she disappears. He opens his eyes and she's just gone and he looks so broken.

7x06 - Slash Fiction

• Sam finally finds out Dean killed his childhood friend Amy, a kitsune, and confronts him. After all the time he tried to get Dean to talk to him, Sam doesn't want to hear it.

7x08 - Season Seven, Time for a Wedding!

• The nicest thing anyone's ever said to Garth is "You don't suck."

7x10 - Death's Door

• The ending, where Bobby sacrifices what's left of his brain to pass on the knowledge he got about Dick Roman's plan to Sam and Dean.
• Just about everything in that episode, from Bobby saying he adopted the boys and they grew up heroes to his mother's anger when he shoots his abusive father. He even tells his younger self "They never thank you."
• Dean's denial. Sam is trying to be realistic and pragmatic and can absorb what the doctors try to tell them that Bobby probably won't make it, but Dean absolutely cannot accept it and refuses to believe until it actually happens.
• The very last scene where Bobby has his final, best memory, which is so simple yet so sweet. When the Reaper asks him if he is going to stay or go, he just looks so torn. Every season, there's at least one episode where they decide to remind us that they have some really good actors on the show. This was it.

7x12 - Time After Time

• Jodi finding a bottle of alcohol in with some of Bobby's things and says that she and Sam should share it. There's a very palpable undercurrent of how she'd considered there to be something that could have been with him that just never was.

7x13 - The Slice Girls

• Emma's death. The look on Dean's face as she bleeds out from Sam's gunshot seems to indicate that he truly wanted to save his daughter.

7x14 - Plucky Pennywhistle's Magical Menagerie

• This fun and lighthearted humorous episode isn't supposed to reduce you to tears, right? Right? Well, your show must be very angst-ridden and tragic if the main characters smiling and laughing can reduce viewers to tears.

7x17 - The Born-Again Identity

• Everything from Sam's deteriorating mental state to Dean's conversations with Emmanuel Allen (Castiel with amnesia) to Castiel taking Sam's insanity onto himself at the end. The entire episode seemed designed to make fans weep.

7x18 - Party On, Garth

• The episode has in its final two minutes Bobby finally returning as a ghost, and trying in vain to get Dean to notice him.

7x22 - There Will Be Blood

• The alpha vampire's reaction to Edgar coldly telling him that they will kill him and all his "children". He refuses to believe it at first, but then looks so honestly upset when he realizes that his "family" has betrayed him. He's a villain, but still...

7x23 - Survival of the Fittest

• The burning of Bobby's flask. It's a questionable mercy that the camera never cuts away from Sam and Dean as they watch Bobby go and we get to see the heartbreak on their faces of saying goodbye to the man who might as well have been their father.
  • Cas watches the "funeral" from the stairs, present but apart. Crazy he may be, but he clearly understands what's happening and that it's a direct result of his actions. It's implied that this is what drives him to join the battle.
• It's kind of expected by now that all Supernatural season finales will have Downer Endings, but still... Season 7 ends with Sam losing everyone he still had left: Dean, Castiel, Bobby, even Meg and poor Kevin Tran were taken in the end.
• Crazy!Cas. Even when he's being funny, it's hard to watch him. Anyone who's seen a loved one in a broken state of mind understands how painful an experience it is.

Season 8

8x01 - We Need To Talk About Kevin

• Dean realizing that Sam didn't even look for him in the year he was gone.
• Kevin's voicemail messages to Sam. He is desperately asking for help, and since Sam didn't answer him, he assumed he was dead or just didn't care.

8x02 - What's Up, Tiger Mommy?

• Dean's casual explanation for why he should have killed Crowley while he was possessing Mrs. Tran. The one line speaks volumes about how far gone Dean is.
  Dean: I mean, yeah, it would've sucked and I would have hated myself, but what's one more nightmare, right?
• On the subject of nightmares and self-hatred, cue a flashback to Castiel screaming for Dean and reaching out to him during their escape from Purgatory, and their hands slipping apart, with Castiel left behind.
• Kevin takes his shell-shocked mother and disappears, having come to believe that Sam and Dean let people die once they have no more use for them, due to seeing Dean try to kill his mother, and a well placed statement from Crowley.
• A very subtle one, but the fact that it's Crowley who calls the Winchesters out on their tendency to 'use people up'; and he seems to genuinely mean it, rather than just using it at a taunt.
  • YMMV, but it's possible that Crowley's distress is related to a certain recent casualty: Bobby Singer

8x07 - A Little Slice of Kevin

• The episode features the long-awaited return of Castiel. Dean has been purposely vague about what happened to Cas during their time together in Purgatory, with the implication that Dean betrayed Cas and left him behind as he was escaping Purgatory. Dean's statements that Cas just "gave up" and "should have fought more" seem to be Blatant Lies, when we see in previous flashbacks it seems like Dean purposefully left him behind. All throughout the episode, Dean is anxious and angry at Cas, with Cas being very patient and understanding. At the very end, we do find out Dean has been lying, but to himself. He didn't leave Cas behind; Cas deliberately pulled HIMSELF away from Dean as he was escaping as he believed he needed to stay behind to atone for his sins. Not only did Dean not betray anyone, but he had beaten himself up over something that wasn't even his fault.

8x08 - Hunteri Heroici

• Despite the episode being mostly lighthearted, Castiel's revelation to Dean that he murdered thousands of angels when he "became God" and that he refuses to go back to Heaven simply because when he sees what devastation he caused he will kill himself was utterly tragic. Especially when looking back at Season 6 where he gave everything to make it a better place.
• There is also the suicide victim. He had invested everything in Richard Roman Industries and lost it all when it crashed and burned the season prior after Dean and Castiel offed Dick Roman. This time, there were repercussions beyond the supernatural.
  • Even sadder is that when he doesn't immediately fall; he takes it as a sign that God wants him to live. Then he looks down.

8x10 - Torn and Frayed

• The entirety of Samandriel's character in general is heartbreaking. When we meet him, he is one of the most adorable and innocent angels the show has ever seen and he only wants what is best for everyone. He loves humans, angels, and is ready to forgive Castiel for what he did in the previous seasons. Then he's captured and tortured for weeks, maybe even months, on end and the only information gotten out of him is from literally breaking into the information hardwired in all angels' heads. Then we have this episode. He's saved by Castiel. We're all happy because we don't have to watch the demons break him anymore. He's safe. Then Naomi uses some Mind Control to make Castiel kill him. His own brother, the one it's implied he always looked up to, the one who saved him, stabs him with an angel blade.
  • Cas' mind control counts too. You can see that he doesn't want to hurt Samandriel or inform on the Winchesters, but he's forced to do it.
  • The way Cas cradles the body, with his head leaned against Samandriel's, is heartbreaking.
  • Blood runs down from the corner of Castiel's eye as a result of the mind control, but it looks almost like tears.
• Dean breaking off all contact with Benny, especially since Benny had asked Dean to help him through a low point.

8x12 - As Time Goes By

• Henry Winchester learns that there is nothing left of the Men of Letters, the secret order he trained his whole life to be part of, and that his son John is already dead. As if that wasn't bad enough, his son died hating him because he thought Henry had abandoned him. After reading through his son's journal, he decides to go back in time to reverse it all from happening, but Dean won't let him because he's afraid that he and Sam will disappear from the consequences of tampering with the past. Henry dies in his grandsons' arms after helping stop Abbadon, now reconciled with his grandsons and with the way things are.

8x14 - Trial and Error

• Dean's admission about how he would take on the trials because he couldn't take giving up on the hunting, while Sam had something to live for, and to keep living for, openly admitting his Death Seeker tendencies.

8x16 - Remember the Titans

• Dean's prayer to Castiel at the end:
  Dean:Cas, you got your ears on? Listen, you know I'm not one for praying 'cause, in my book, it's the sa– It's the same as begging. But this is about Sam, so I need you to hear me. We are going into this deal blind, and I don't know what's ahead or what it's going to bring for Sam. Now he's covering pretty good, but I know that he is hurtin'. And this one was supposed to be on me. So for what we've been through, [he closes his eyes, pauses for a moment] I'm asking you, you keep a lookout for my little brother, okay? [stops, looks around] Where the hell are you, man?
  • Especially tear-jerking considering the last time he and Castiel spoke, Cas admitted to some serious suicidal tendencies. With what Cas then had to do, and the way they left each other, for all Dean knows, the guy's gone through with it.
  • Also, when you recognize the music that's playing, it gets worse. It's "Americana," the same music that played during Chuck/God's voiceovers in "Swan Song."

8x17 - Goodbye Stranger

• Dean pleading with Castiel to overcome his Mind Control near the end.
  Dean: It's me. We're family, we need you. I need you.
  • Not to mention when Dean flinches away from Cas like he's expecting to be killed, though Cas heals him instead.
• Meg, full stop. She's a demon, so her motives are almost always suspect, something she herself lampshades. But she seems genuinely upset that the boys never bothered to search for her after Crowley's goons nabbed her in Season 7, mirroring Dean's angst over Sam not looking for him. She also appears to have developed some sort of attachment to Castiel, even drawing connections between him and Sam's ex, Amelia, to whom she refers as a unicorn. And at the very end, Crowley kills her right in front of the Winchesters, who only watch and escape.
  Meg: Go save your brother...and my unicorn.

8x19 - Taxi Driver

• Benny's Heroic Sacrifice to save Sam and Bobby from Purgatory. He proved to Sam that not all vampires are monsters. And he did it willingly, knowing that the temptations of Earth were just too much for him and that he didn't want to hurt anyone.
  • Even more so when you realize how good of a friend Benny was. Dean abandoned him and left him to fend for himself after Benny saved his life so many times in Purgatory; yes, Dean did repay the favor, but he still abandoned Benny because Sam couldn't accept a good vampire. And when Dean comes back asking Benny to die to save Sam, a guy who wants him dead, Benny still says yes because it's Dean asking. He was still willing to die for Dean even after his rather cruel breaking of their friendship to save a guy who would kill Benny just for existing. Now that is a friend.

8x20 - Pac-Man Fever

• The ending. Charlie signs the paperwork to take her mom off life support and then sits down to read The Hobbit to her one last time.

8x21 - The Great Escapist

• Castiel comes up with a strategy to hide from Naomi by teleporting through a huge restaurant chain. Naomi stops him by slaughtering an entire restaurant of people, save one waitress whose eyes have burned in their sockets, mumbling over and over desperately that he has to stop. Cas is terrified and on the verge of tears. It's a shame Metatron got to Naomi, first. She didn't suffer nearly enough.

8x22 - Clip Show

• This might just be the most depressing episode yet, and since it's the episode before the season finale, that is saying something. It's not even the "oh my god there's this super-powerful enemy that we have no chance of defeating, but we have to" type of pre-finale episode. It's just... hard to actually see everyone coming out of this mentally whole, not even worrying about if someone dies. For instance, as the girl dies from Crowley's spell and Crowley finishes his speech, Dean throws the phone at the wall, breaking it. The hex bag they needed to save said girl was inside.
• Dean not accepting Castiel's apology. Just the looks on their faces...

8x23 - Sacrifice

• Castiel watching all of the angels fall from Heaven after falling himself. You can tell by the look on his face that he already blames himself.
• Surprisingly enough, after fans declared their undying hatred of Crowley and Naomi, their hearts broke for them.
  • Crowley starts turning back into a human, complete with a Villainous BSoD in which he tearfully reveals he just wants to be loved (something which had been warped by Hell into greed).
  • Naomi, meanwhile, has a Heel–Face Door-Slam when she realizes that she has lost her way, tries to stop Metatron's Evil Plan and make amends with a wary Castiel; and gets attacked by Metatron off-screen. We learn in Season 13 that she survives the attack, though, and judging from what we see, she is on her way to redemption.
• Crowley bearing his soul and regaining (at least for the moment) his lost humanity. Mark Sheppard delivers magnificently and the scene is absolutely heartbreaking.
  Crowley: Would it be possible, moose. I'd like...to, uh, ask you a favor. Sam...earlier when... you were confessing...back there. What did you say? I only ask because...given my history...it raises the question...(Crowley begins to tear up) where do I start...to even look for...forgiveness...I mean.
  • Then a bit of a heartwarming moment:
  Dean: [holding the blood syringe] How about we start with this?
  [Crowley then pauses and willingly accepts continuing the ritual]
• Dean and Sam's conversation towards the end.
  Sam: You want to know what I confessed in there? What my greatest sin was? It was how many times I let you down. I can't do that again.
  Dean: Sam—
  Sam: What happens when you've decided I can't be trusted again? I mean, who are you gonna turn to next time instead of me? Another angel, another... another vampire? Do you have any idea what it feels like to watch your brother just–-
  Dean: Hold on, hold on! You seriously think that? Because none of it, none of it, is true. Listen, man, I know we've had our disagreements, okay? Hell, I know I've said some junk that set you back on your heels. But, Sammy... come on. I killed Benny to save you. I'm willing to let this bastard and all the sons of bitches that killed Mom walk because of you. Don't you dare think that there is anything, past or present, that I would put in front of you! It has never been like that, ever! I need you to see that. I'm begging you.
  • "Come on. Let it go, okay? Let it go, brother."
    • And then Sam Heroic RRoDs.

Season 9

9x01 - I Think I'm Gonna Like It Here

• Dean's worry over Sam is heartbreaking.
• Sam is so desperate to not hurt anyone that he specifically asks Death to make his death permanent and not allow him to be resurrected.

9x03 - I'm No Angel

• Castiel's struggles with homelessness and hunger and his sudden understanding of how difficult being human is is heartbreaking. Then, he finds brief respite and safety with April, only for her to torture and kill him.
• Castiel's (brief) death and his reaction to Dean telling him to leave. His large Puppy-Dog Eyes just make it worse.
  • Dean's reaction to thinking his best friend is dead, especially the little sob in his voice when he yells "Cas!"

9x06 - Heaven Can't Wait

• Castiel's face when he realizes that he doesn't have a date; he's just been asked to babysit.
• He starts singing "Walking on Air" to comfort the crying daughter of his co-worker. The first couple lines sound like he's choking back his depression ("Look at what's happening to me/I can't believe it myself...")
• The fact that he's willing to stand up to a powerful angel while being human, only to discover that it is his pain the angel came to put an end to and not the baby's.

9x07 - Bad Boys

• The entire episode reveals that when sent to a group home at sixteen, Dean thrived. He even met a girl and had his first kiss. Before being able to take her to a school dance, John shows up to take Dean back to their life of hunting. Dean goes, standing up the girl and choking back tears.

9x09 - Holy Terror

• Everything goes downhill when Kevin snaps at Dean by saying every time he trusts the brothers, he gets screwed over.
• Made worse when the episode's end proves him right. Gadreel, who has been posing as Ezekiel and possessing Sam, tricks Dean, kills Kevin, and tells Dean that Sam is gone.
• The episode's final scene also drives it home: Dean sitting on the floor, crying and just repeating Kevin's name.
• Seeing both sides of the Enemy Civil War killing each other's vessels and potential vessels is sad, given how it boils down to idealistic Bible study students and born-again PTA members who believe in the goodness of the Angels being killed by them as part of a power struggle.

9x10 - Road Trip

• The beginning manages to top the ending of the previous episode in the first couple of minutes. Dean has given Kevin a hunter's funeral and he is so torn up over Gadreel killing Kevin that he walks around aimlessly, looking through Kevin's stuff (including his cell phone) before angrily throwing the stuff around.
• Despite Dean's rejection of Castiel when he was incredibly vulnerable, a re-powered Castiel comes when Dean calls and listens to Dean pour his heart out.
• When Sam gets his memories of his time possessed by Gadreel back, he looks heartbroken as he asks "Did I kill Kevin?" Crowley reassures him that Sam didn't; Gadreel did.

9x11 - First Born

• The end of the episode when Dean has been given the Mark of Cain and Crowley gives some wise words which, when you think about it, is true. Dean took the Mark of Cain without any hesitation even when Cain told him it carries a terrible price. Dean thinks so little of himself that he doesn't even hear out what that price is; he just accepts the Mark. Dean only remembers his failures—breaking in Hell and torturing souls; failing to save Sam from the Cage, the collapse of his life with Lisa and Ben; his failure to protect Kevin, and the fact that everyone he cares about either betrays him or dies, and he believes that he is responsible for that. Since he views his failures as greater than his successes, which he is incredibly wrong about, it's no wonder he hates himself.
  Crowley: Your problem, mate, is that nobody hates you more than you do. Believe me, I've tried.
• Sam saying that he and Dean can either work together or be brothers—that he can't trust Dean anymore and all their failures are because they're family. Dean can't even answer, just nods.

9x14 - Captives

• Dean's speech to Ghost!Kevin, apologizing for causing his death. And then Ghost!Kevin appears, pissed that Dean's going off on another pity party. Still, he forgives him.
  Dean: Kevin, I'm sorry. You did not choose this life. You busted your ass, you lost everything, everyone you've loved... And your reward? Getting killed...on my watch. If I... It was on me. It was my fault, and...
• Despite the hell Linda's been put through, she just wants to escape so that she can, and here's the kicker, see Kevin again. And it isn't until near the end of the episode that she learns her son is dead.
• Kevin's last request before leaving with his mom was that Dean and Sam deal with their current issues with each other and try to work them out. As soon as he leaves, Dean turns around... and sees Sam leave the room.

9x15 - #THINMAN

• The breakup of the Ghostfacers can be seen as a downer given that it mirrors Sam and Dean's recent estrangement and, unlike the brothers, they might not reconcile. Or rather, just like Sam and Dean.

9x17 - Blade Runners

• Crowley falling off the wagon. After killing Lola for betraying him, he looks around at the wreck of his room, then glances in the mirror and closes his eyes in despair. The look of an addict realizing how far he's fallen is heartbreaking.

9x21 - King of the Damned

• Despite his best efforts, Crowley starts to care about his son. His voice even breaks slightly when he discusses how his son died when the ship he was on went down in a storm.

9x23 - Do You Believe In Miracles?

• "I'm proud of us." And the entire scene that follows.
• Also, the fact that apparently Castiel had been doing everything in this season just to save Dean. And he failed.
• Also, consider this: Remember how, in "The Purge", Sam stated that, if he were in Dean's situation near the start of the season (his brother nearing death with a slim hope of bringing him back), he wouldn't have tried to save Dean? Come this episode, we see that Sam just can't do it. The last we see of Sam this season is him storming off to where Dean summoned Crowley, tears in his eyes, setting out to force Crowley to save Dean.

Season 10

10x01 - Black

• Seeing how far Sam has gone in his quest to find Dean is heartbreaking. Torturing demons, driving himself into the ground, and going on even with a broken arm.
• Castiel's state since Metatron's defeat. He's dying and the only way he can help himself is to kill an angel and take their grace, something he won't do. And due to an unexplained incident, he can no longer help Sam.
• Deanmon's Breaking Speech to Anne Marie proving just how callous and uncaring he has become. The poor girl even laments how screwed up she is because she actually feels that she deserves what Deanmon said to her.
• Deanmon practically telling Cole that he doesn't care if Cole slits Sam's throat since Deanmon made it clear to Sam not to come looking for him. After ten seasons and twenty years of looking out for little Sammy, Deanmon has finally stopped caring.
• The mission that Hannah undertakes with Castiel to force two recalcitrant angels to return to Heaven when all they want to do is stay on Earth and live freely proves that, since the Apocalypse, the Civil War, the Fall, and the return to Heaven and all the lessons about free will and choice that Castiel has tried to impart to them; the angels as a race have learned absolutely nothing.

10x02 - Reichenbach

• Cole's entire life seems to be a bit of a Tear Jerker, if you consider his speech to Sam and what happened when he was a child, finding his dead father and then his killer, Dean:
  Sam: I don't know how to tell you this, but...there are monsters out there.
  Cole: You don't think I know that? I did two tours in Iraq. Special ops. Darfur. The Congo. I've seen suicide bombers and child soldiers so hopped up on speed that they could barely talk, but they could sure as hell shoot an AK.
  Sam: Not that kind of monster.
  Cole: Don't tell me about monsters! 'Cause I've met my share.
• Deanmon showing yet another way he has changed. He no longer cares about the Impala:
  Sam: This thing's filthy.
  Deanmon: It's just a car, Sam.
  Sam: "It's just a car?" Wow, you really have gone dark.
• Sam in his confrontation with Deanmon. He's trying so hard to convince himself that Crowley is behind Deanmon's behavior and that his brother is still there, and Deanmon slowly breaking that illusion down. And at the end, when Deanmon explains exactly why he let Cole live, and you can see Sam's last hope that his brother is still there die.
  Sam: You know what, Dean? I saw what happened back there. You could have killed that guy and you didn't. You took mercy on him.
  Deanmon: You call that mercy? Imagine you spend your whole life hunting down the guy that knifed your father. When you finally find him, he whips you like a dog. How do you think that feels? That kid is going to spend his whole life knowing that he had his shot and that he couldn't beat me. That ain't mercy; that's the worst thing I could have done to him. And what I'm gonna do to you, Sammy, well, that ain't gonna be mercy, either.
• Crowley looking at the picture of himself and Deanmon during their vacation. Hard to think you'd feel sorry for the King of Hell, but he really wanted to be Deanmon's friend, yet ultimately Deanmon is the bigger bastard.

10x03 - Soul Survivor

• Deanmon's speech to Sam, with Deanmon calling Sam out on corrupting Lester into making a deal just to track Deanmon, and pulling a Calling the Old Man Out on John in blaming him for turning both Dean and Sam into hunters just drives home how messed-up both Winchesters actually are.

10x05 - Fan Fiction

• During the final line-up of the cast, Sam and Dean see a character they don't recognize, with Maeve explaining that it's Adam, John's other son who's stuck in Lucifer's Cage forever. While she's saying this, pay attention to Sam and Dean's faces; they have clearly forgotten up until this point that Adam even existed.
• The "Carry On My Wayward Son" number, especially since the most important parts are sung by someone who is supposed to be Mary, Dean and Sam's departed mother. It's like their mother is telling the boys to carry on because once they're done, they'll finally have peace.
  • If you pay attention to their expressions, it's even more heartbreaking. Sam's reaction [1]◊ is one of hope——just look at his little smile at the end. On the other hand, Dean's [2]◊ is weary and cynical. He knows better. He know that there is no rest, and there will never be peace.
• Chuck/God telling Marie, a girl who was made fun of, laughed at, and jerked around by monsters, that her play was good and he liked it was tear-worthy. When God Himself tells you he likes something you did, you know that you aren't a joke, no matter what other people say.

10x06 - Ask Jeeves

• Even though she was the villain, Olivia had a rather tragic backstory. On the day she was born, her birth father, a shapeshifter, killed her mother's husband and tried to take her from her mother, only for Bobby to kill him instead. Then Bobby agreed to spare her life on the condition that her mother keep her locked up in the attic.

10X07 - Girls, Girls, Girls

• Hannah's genuine remorse for destroying her vessel's life by taking her as one. Someone finally asked the question, what about the people that the vessels leave behind, and they got the answer. It wasn't a good one.
• Castiel talking about how he took Jimmy Novak from his family. He says it was necessary, but you can see in his face that he's not sure about that anymore and that he wishes he could have left him alone.
• Castiel googling Jimmy at the end, and the first result being tributes to him and a missing poster.
• Dean's speech to Cole is a real Tear Jerker, especially after the rendition of "Carry On Wayward Son" in "Fan Fiction."
  Dean: I get it. That was your story. Look, man, I got one of those too, okay? But those stories that we tell that keep us going, sometimes they blind us. They take us to dark places, kinda place where I might beat the crap out of a good man just for the fun of it. The people who love me, they pulled me back from that edge. Cole, once you touch that darkness, it never goes away. Now the truth is, I'm past saving. I know how my story ends; it's at the edge of a blade or the barrel of a gun. So the question is is that going to be today, it gonna be that gun?
  • And after that when Sam asks him if he was being truthful. Dean says he wasn't, but his face clearly claims otherwise.
    Sam: What you said earlier back there, about being past saving were you really—
    Dean: I was just telling the guy what he needed to hear. We better go.

10x09 - The Things We Left Behind

• The absolute wreckage of Claire's life after Castiel took her father as his vessel. Her mother abandoned her shortly afterwards to "find herself", her grandparents died and left her to be bounced around foster families, she's in and out of group homes (or, as Cas terms it, "child prison"), and clearly messed-up by what happened to her father. And the person she trusts the most is a skeevy gambler who uses her to commit robberies and sold her to a loan shark in exchange for a deal on his debt.
• Castiel's gutted expression when Claire flees from him. He really thought he could help her.
• Dean asking Castiel to smite him if Deanmon rears his ugly head again. Dean would rather die than become Deanmon again.
• Crowley recounting his utterly godawful childhood with Rowena who abandoned him at age eight and once tried to sell him for three pigs. Is it any wonder he turned out the way he did?
• Sam's utter horror when Dean massacres the loan shark and his men; he looks so desperate to believe that Dean had no choice. And all Dean can say is that he didn't mean to do it.

10X14 - The Executioner's Song

• Literately, everything about Cain is this. After killing all those demons, as he had already expected, he fell back under the Mark's influence and started killing his descendants because he knew extinguishing them would help him make up for having committed the first murder and starting the very idea of murder in the first place.
  • Also, his relationship with Dean. Cain genuinely feels killing Dean would be saving him from his fate as he knew the Mark would inevitably transform him into the same monster he is now. Compare that to how he used to be resistant to the Mark and anyone would feel sorry about him.
    • Dean himself is clearly saddened and devastated to see his ancestor act like this. Not only is it a grim reminder of the fate that seems so inevitable, but it also reminds him of how Cain is effectively what he would be like if he killed Sam and just gave up. Even though at this point it's effectively a Mercy Kill, it's still heartrending for Dean to do.

10x20 - Angel Heart

• Amelia's death and Claire's reaction to it. Especially since the two have just had a heartfelt reunion after nearly six years of separation.
  • Also, Amelia dies because she protected Claire from Tamiel's attack.
• Amelia being greeted by Jimmy in Heaven is both this and heartwarming. After all she's been through, she does finally reunite with her husband...even if not in life.

10x21 - Dark Dynasty

• Dean tears into Sam for lying to him about the Book of the Damned and getting Charlie involved in the whole mess.
• The end of the episode, where the Winchesters arrive at the motel to find Charlie's dead body in the bathtub.

10x22 - The Prisoner

• Dean not-so-subtly telling Sam that he wishes Sam had died instead of Charlie, and Sam's reaction, which is to not argue against it. Heart-breaking even before it aired for fans who watched it on the preview clip.
• Crowley has returned to being full demon... because Sam hurt him with the witch box, called him a monster, and reminded him about all his evil deeds, while it seemed that Crowley tried to take a level in kindness. Sam has only survived because Crowley allowed that.
• Dean kills all the members of the Styne family, including Cyrus, who was just a young man who was disgusted and terrified by what his family was and even told Dean so as he begged him not to kill him. Then Castiel appears, tries to stop him, and Dean nearly kills him...
  • The tragic part is how it almost mirrors John's obsessive need for revenge against Azazel. Dean has pretty much turned into a scarier version of his own father.

10x23 - Brother's Keeper

• Dean taking a level in jerkass with regards to not just the dead victim, but implying that her parents were abusive toward her. He also startles the vampire holding Rudy hostage, which makes the vampire kill Rudy. After killing the vampire, Dean is remarkably callous to the victim who is now safe, but still traumatized from having been kidnapped and the fact that Dean let Rudy die.
• Crowley's speech about his mother's lack of love toward him. It hurts, no matter how little he wants to let it show.
  Crowley: All my long life, I wondered what I'd done to deserve a mother who refused to show love. I pained over it. I built my bloody kingdom on top of it. Then one day, epiphany struck. My mother was incapable of loving anything. For the first time in hundreds of years, I felt free. And then you showed up in my dungeon, we communed, and I began to realize you weren't incapable of love. You're incapable of loving me.

• Rowena killing Oskar, the only person she truly loves, as one of the requirements for freeing Dean from the Mark of Cain is to kill a loved one. All while Crowley watches with a smile, clearly relishing every moment of psychologically torturing his abusive mother.
  • As Season 12's "Family Feud" reveals, she hasn't moved on from this, and the event eventually bites Crowley in the back. See below. Crowley's family really is screwed up.

Season 11

11x01 - Out of the Darkness, Into the Fire

• In this episode people get corrupted by the released Darkness and start killing each other. Especially the scene when the father of the girl, who lost his wife, and his daughter either has become the Darkness or is somehow connected to her, gets corrupted, and begs the brothers to save his girl.

11x02 - Form and Void

• Jenna Nickerson got her soul eaten by Amara. And Crowley brings more people, including children, for Amara to eat.
• Castiel suffering Cold-Blooded Torture at the hands of his angelic siblings with tears streaming down his face. Even worse, when Hannah shows up, she's not even there to help him. She's there to play at being a "good cop."
  Castiel: Mercy, brother, please!
• Sam praying in the hospital's chapel.
  Sam: [takes a deep breath] So, I know it's been a long time, but...Dean and I, we've been through a lot of bad, but this is different. This is my fault, and I don't know how to fix it. And if I have to die, I've made my peace with that, but...please, Dean deserves better. Dean deserves a life. There are people out there, good people, who are going to suffer because of me, and I am not asking you to clean up my mess, hell I don't even know if you're out there, but if you are, and if you can hear me, I...we...need your help, God. We need to know there's hope. We need a sign.

11x09 - O Brother, Where Art Thou?

• Take into account everything that Sam and Dean have been through: What happened to not only their parents, but their entire family, the numerous friends they've lost, the multiple times that the two of them alone have been spared, finding out that they were destined to be the hosts of another set of brothers that would force them to fight to the death, Dean being sent to Hell, Sam being locked in the Cage with Lucifer and Michael, Sam losing his soul, Dean turning into a demon, etc. Despite all of that pain and suffering, which alone would be more than enough to cause anyone to lose faith, Sam is able to find some hope and belief in the visions that he's been receiving, coming to the conclusion that they are from God. Therefore, he is able to get over his fear and face Lucifer, even when he finds himself trapped in the Cage with him once again. How is he rewarded? By finding out that it was never God sending him the visions at all, that it was Lucifer all along. This revelation is enough to get Sam to actually shed a tear.

11x10 - The Devil in the Details

• They're both terrible people, but Rowena's speech to Crowley about why she hates him really drives home how broken they both are.

Rowena: I hate you, because when I look into your eyes I see the woman I used to be, before magic, before the coven... when I was nothing but Rowena, the tanner's daughter... a pale, scared little girl, who smelled of filth and death. I hate you, because when you were born, your father said he loved me, then he went back to his grand wife and his grand house, whilst I lay pathetic and half dead on a straw mat... my thighs slick with blood. I hate you, because if I didn't, I'd love you. But love... love is weakness. And I'll never be weak again.

11x14 - The Vessel

• Crowley is on the leash and in chains, like a dog, which Lucifer actually calls him. And he seems to be so broken (or at least playing along) that he even mocks demons who dare to give advice to the Devil. It's only made a little better by The Reveal that he was only biding his time.

11x17 - Red Meat

• No matter how many times it happens, Dean's reaction to Sam's death is heartbreaking.

11x18 - Hell's Angel

• According to her to Rowena, Amara has never had anybody to confide in before.

11x19 - The Chitters

• Jesse and the old sheriff's stories. The old man just sounds so heartbroken when he talks about his daughter. And when Jesse finds his brother's body... Good god.

11x20 - Don't Call Me Shurley

• The audience has been waiting for years for Metatron to be brought down to size, but when Chuck/God finally delivers him "The Reason You Suck" Speech, it just felt more harsh than satisfying. Probably because Metatron was finally showing signs of changing.
• Chuck/God explaining he made Creation because he was lonely, since Amara was his antithesis (he being light and being; she being nothingness and darkness), so he tried to make things to show his older sister that there could be more than just the two of them and they didn't have to be alone...only for Amara to just keep destroying the worlds he made, ultimately forcing him to seal her away.
• Due to the influence of the fog, Sam admits to Dean that he's afraid Dean's gonna choose Amara over him. He instantly takes it back and tells Dean to leave him before he's forced to hurt him. Dean refuses.
  Sam: We're not gonna make it.
  Dean: No-no-no. There's no quittin' here.
  Sam: We were never gonna make it.
  Dean: Sam that's not you talking, it's the fog.
  Sam: You're gonna choose Amara. Over me. Over everything.
  Dean: Sam, No!
  Sam: I'm sorry, I didn't mean it. I can't fight this, you gotta go. You gotta get out before you get infected. Before I hurt you.
  Dean: No. I'm not leaving you. Ever!
  • Adding to this, Dean tries to get himself infected by deeply breathing in the fog, but it does nothing as Amara is protecting him.
  • Also, this is the second time within four episodes where Sam almost dies.
• All the damage and death that Amara caused is fixed by Chuck/God, even the people who died are resurrected, resulting in perhaps the very first Everybody Lives ending in Supernatural. And it is glorious, enough to make you weep with happiness as Sam and Dean leave the police station and see everyone restored, even the friendly deputy and her husband who died earlier on. Chuck/God didn't go halfway here; he saved everyone.

11x21 - All in the Family

• The ending, with Lucifer and Chuck/God reuniting for the first time in millions of years. Especially with the suddenly very quiet, very fragile voice of Misha Collins in saying "You've changed", almost as if he's in such a state of shock he can't think of anything to say other than repeating it back. Notably, it manages to instantly reverse, even if only for the one moment, much of Lucifer's goofier, more obnoxious slide into Villain Decay and restore some of the gravity and tragic qualities from Season 5 that'd been dropped from his character in later appearances. See here.

11x22 - We Happy Few

• The tone in Amara's voice when Chuck/God starts to lock her up again in the Mark is more than just a Villainous Breakdown. It's pure terror. Think about it. As the previous episodes hinted, while Amara hates her brother for wanting something other than her, she also Hates Being Alone, which was exactly what happened to her for billions of years before the Season 10 finale (compare Lucifer, whose imprisonment couldn't be more than a few hundred thousand years). She had been locked up in what we assume an empty place since before the beginning of Creation. At least Lucifer had demons to care for him and everyone knew him (not that it's a good thing). Amara not only had no one for company, nobody except for six beings in this universe even knew who she is. And now, she is going to get locked up again.

11x23 - Alpha and Omega

• Despite all the pain she has caused, Amara's regret after seeing what her almost killing Chuck/God out of spite is doing to Earth manages to tug at the heartstrings.
• The last time we see Sam this season, he may or may not have been shot by Toni Bevell of the British Men of Letters. It gets sadder when you remember that Sam has no idea that Dean is alive.

Season 12

12x03 - The Foundry

• Mary has to leave her sons because, after everything, she still feels out-of-place. She thought hunting with her boys would help her cope because, when she's with them, she's just reminded of how much time she lost. How her sons are no longer her sons from before she died. Not to mention how out-of-touch she was with everything (like using computers). She decided she had to leave them to "find herself." While Sam is a little more understanding, Dean doesn't take it well and won't even look at his mom. And this is after Dean is very happy to have her back and didn't want to see anything was wrong.

12x04 - American Nightmare

• Poor Magda is assassinated by Ketch before she can even start to have a normal life.

12x07 - Rock Never Dies

• There's no denying Lucifer's a Jerkass through and through and that nothing can justify his actions, but his Motive Rant to Team Free Will about how he's causing mayhem because he feels betrayed by how God left right after they made up isn't exactly birds and sunshine.

12x11 - Regarding Dean

• Although humorous at first, the memory erasure spell begins to take an Alzheimer-like toll on Dean. When he tries reciting the most important information (his name is Dean, Sam is his brother, Mary is his mom, Castiel is his best friend), even that disappears little by little, and almost pushes him to tears.

12x12 - Stuck in the Middle with You

• Castiel's speech as he lies dying from a wound inflicted on him by Ramiel with Michael's Lance.
  Castiel: No, you listen to me. You... Look, thank you. Thank you. Knowing you, it...it's been the best part of my life. And the things that...the things we've shared together, they have changed me. You're my family. I love you. I love all of you. Just please, please, don’t make my last moments be spent watching you die. Just run. Save yourselves. And I will hold Ramiel off as long as I can.

12x13 - Family Feud

• Crowley tries to stop Gavin from going back in time to the shipwreck that was supposed to kill him. Rowena paralyzes him with a spell, and all he can do is stand there, one hand outstretched, while Gavin leaves. He looks like he's about to cry.
• Then Rowena tells Crowley that she convinced Gavin to go to the past and prevent his girlfriend from turning into a vengeful spirit, Crowley knows that there's a more petty reason for this, which she admits was him killing Oskar. Crowley's not by any means a good demon, but you can really feel for him there.

12x16 - Ladies Drink Free

• Hayden and Ben's mother is implied to be a single parent and ends up losing both of her children in the span of a few days.

12x20 - Twigs & Twine & Tasha Banes

• The witch showing Dean and Max how she killed Tasha and created the facsimile of her. The look on Max's face as he's subjected to the sheer torture of watching his mom murdered is gut-wrenching.
• And as if Max hasn't been through enough already, he loses his sister. And the last thing Alicia sees is her mother stabbing her. He so can't accept another loss that he brings Alicia back to life as a twig-person. This comes after Sam expresses his belief that he'll be okay.

12x21 - There's Something About Mary

• Toni's "Reason You Suck" Speech to Mary, how she allowed Azazel to come to her house for Sam and what became of John after her death, the latter of which her sons never really told her about.
• Eileen's death, and Sam's reaction to learning the news.
• Dean attempting to get through to a mind-controlled Mary in the Bunker. It doesn't work.

12x22 - Who We Are

• To free Mary from the BMoL's brainwashing, Dean enters her mind and finds himself in a dream world where Mary is being "the perfect mother." He tries to make her aware of this false reality, then launches into one of the show's most heartbreaking speeches.
  Dean: I hate you. You lied to me. I was a kid. You promised you'd keep me safe, and then you make a deal with Azazel. Yeah, it saved Dad's life, but I'll tell you something else that happened, because on November 2, 1983, old Yellow Eyes came waltzing into Sammy's room because of your deal. You left us. Alone. Because Dad was just a shell. His perfect wife, gone. Our perfect Mom, the perfect family, it was gone. And I-I had to be more than just a brother. I had to be a father, and I had to be a mother. To keep him safe. And that wasn't fair. And I couldn't do it. And you wanna know what that was like? They killed the girl that he loved, he got possessed by Lucifer. They tortured him in Hell and he lost his soul. His soul. All because of you. All of it was because of you... I hate you. I hate you, and I love you. 'Cause I can't—I can't help it, you're my mom. And I understand. Because I have made deals to save the ones I love, more than once. I forgive you. I forgive you. For all of it. Everything. On the other side of this, we can start over, okay? You, me, Sam. We can get it right this time. But I need you to fight, right now. I need you to fight. I need—I need you to look at me, I need you to really look at me and see me. Mom, I need you to see me. Please.

12x23 - All Along the Watchtower

• Crowley's sacrifice. Evil though he was, it's still sad to watch him die.
  Crowley: [to Dean and Sam] Goodbye, boys. [stabs himself]
• Castiel's death. He exits the dimensional tear, Dean and Sam are relieved, and we're led to think he either killed Lucifer or at the very least gravely wounded him, then WHAM! Cas gets stabbed through the chest with an Angel Blade, his Grace lights up and then fades, and he falls to the ground, revealing Lucifer standing behind him. Luci then rubs salt into the very fresh emotional wounds by commenting on how "fun" it was.
• Mary's Heroic Sacrifice manages to be both sad and awesome. She uses Enochian brass knuckles to punch Lucifer back into the dimensional tear and falls through with him. Dean and Sam's reactions to watching their mother, with whom they spent the past season connecting, fall into a crapsack alternate dimension is heart-wrenching.
• The whole episode, in a nutshell. In a span of a single day, Dean and Sam lose four of their closest allies, including Rowena, Crowley, Castiel, and their mother Mary (the last three within minutes of each other, no less!). They also lose Kelly, who dies giving birth to a being nobody is sure what to make out about. The only silver lining of this whammy of an episode is that they manage to keep Lucifer at bay, but holy hell, this is arguably the most depressing season finale of Supernatural, and that is saying a lot.

Season 13

13x01 - Lost and Found

• Dean is overwhelmed with grief from losing Castiel and his mother. AGAIN. He prays for Chuck/God to bring them back
  Dean: Because after all we've been through, you OWE US, you son of a bitch! So you get your ass down here, and you make this right, right here, right now!
  • When nothing happens, Dean furiously punches a sign so hard that his knuckles bleed, then prays again, more desperately, "Please... help us." And still, nothing happens. Dean thus loses his faith in God and walks away.

13x03 - Patience

• Dean's rage at Jack is so clear, yet his sadness makes him sympathetic. He misses Castiel deeply and blames Jack for it.
  Dean: [to Sam] He manipulated him. He made him promises. Promised him paradise on Earth. And Cas bought it, and you know what that got him? It got him dead! Now you might be able to forget that, but I can't!

13x05 - Advanced Thanatology

• Dean telling Billie to reap him, saying that his constant failures and mistakes (to name the most recent few, Castiel's death and Mary's uncertain fate in Apocalypse World) are beginning to weigh him down.

13x10 - Wayward Sisters

• Kaia's death^note She gets better and Claire's reaction to it. Made even worse when Jody reveals in later seasons that Kaia was Claire's first love. Imagine, just falling in love with someone and then lost that someone in the span of twenty-four hours. Sam mention he tried to talk with her, but Claire was so deep in her grief that didn't even seem to listen.

13x11 - Breakdown

• Sam blaming himself for Kaia's death. Made worse with the implication that his guilt is less about Kaia's death and more about how much that death hurted Claire because, not only he knows Claire's grief better than anyone (Eileen's death in the last season is clearly still fresh in his mind), he also knows how losing a loved one can lead to a path of revenge (like what happened with John Winchester after Mary's death).

13x12 - Various & Sundry Villains

• Rowena and Sam having an honest-to-God talk about seeing Lucifer's true face and how they cope with it is a mix of this and heartwarming.

13x16 - ScoobyNatural

• Watching Fred and Shaggy get hurt during the fight with the Phantom.
• Sam, Dean, and Castiel telling Mystery Inc. the truth about the supernatural. The gang doesn't take it well when they realize the implications; Shaggy, Scooby, and Daphne are hit pretty hard and go into a full Heroic BSoD. Just watching them lose their childlike innocence is both funny and tragic. It disturbs the Wayward Boys so much that they ask the real ghost to disguise himself as Cosgood Creeps to calm them down.
  Daphne: Am I going to Hell?!
  Scooby: We're doomed.

13x17 - The Thing

• Gabriel, full stop. With Asmodeus taking his grace for himself, whilst keeping his mouth sewn shut, and lots of implied Cold-Blooded Torture, he is now a shaking, whimpering mess of what he once was.

13x18 - Bring 'em Back Alive

• Gabriel’s on the road to recovering from the trauma he endured at the hands of Asmodeus, but just hearing the Prince’s voice over the phone is enough to make the poor angel recoil in terror, not to mention when he realizes Asmodeus knows where he is and is coming to take him back.
• Dean telling Ketch why he is so insistent on saving Apocalypse!Charlie: He failed his world's Charlie, and he's not going to make the same mistake and miss his second chance to rectify it. All while flashbacks of Charlie's death are shown. He barely manages to hold back his tears. The fanbase, not so much.
• Dean's meltdown at the end, when Castiel and Sam break the news of Gabriel disappearing again without leaving them anything to work with. The episode is already one big "Shaggy Dog" Story for him (not being able to meet and rescue Jack and Mary; Apocalypse!Charlie snubbing his offer to enter the main world, and Ketch choosing to stay in Apocalypse World), then that comes out. Poor Sam actually visibly flinches; it's almost like he's a kid being scolded by his father (which is, to an extent, true).

13x19 - Funeralia

• The revelation that Rowena has been killing reapers to force Billie to appear and resurrect Crowley, whose death she has great remorse for.
• They have done plenty of horrible things and you have legitimate reasons to hate them, but you've got to feel bad about the angels when we learn from Naomi the reason why they are becoming so desperate throughout this season. It turns out that killing a race that can't reproduce by themselves will result in that race slowly dying over time, and that's that: Angels have been reduced from the thousands to a handful. And this affects the survivors' mental state. One angel has fallen on hard times enough to become a drunkard (note that angels are far more resistant to alcohol). Others silently allow Lucifer to lead them (not that he does a great job at it). Even Naomi, the same controlling and power-hungry monster from Season 8, has become so defeated that she resigns herself to fate while telling Castiel to find any help he could. Castiel (who, let's face it, has a big responsibility for this predicament) mostly goes silent the moment Naomi begins her lecture.

13x20 - Unfinished Business

• Apocalypse!Kevin breaking down while explaining that the reason he works for his universe's Michael and willingly offers himself as a bait to kill the Resistance members present is so he can reunite with his mother again.

13x21 - Beat the Devil

• He may be an asshole, but seeing Lucifer drowning his sorrows at a bar and bitterly rejecting Heaven and Hell is rather poignant. Especially since he shows a brief moment of humanity when he mentions that the only thing that matters to him is his son Jack, all while set to "Cat's In the Cradle" by Harry Chapin. And even though it may have been that Lucifer is nothing but a Spoiled Brat throwing a temper tantrum, it is sad in a sense to see the Devil being reduced to a rambling drunkard.
• Yes, it's been done a bazillion times before, but seeing Dean openly crying for Sam's (temporary) death is still painful to watch.
  • For that matter, although her reaction is subdued, this episode is the first time Mary gets to experience the death of a son ("The Song Remains the Same" doesn't count, as her memories of the events were erased by the main universe version of Michael). Sam comes back, of course, but just imagine if he didn't. Recall that she spent the whole previous year mourning for, among others, John.

13x22 - Exodus

• The Winchesters spent eight years mourning for a supposedly dead friend and were overjoyed when he was miraculously revealed to be alive. Fast-forward to five episodes later, and Gabriel is killed. Again.

13x23 - Let the Good Times Roll

• After Jack violently confronts a man he suspects killed Maggie and Dean is forced to shoot him to get him to back down, he heads off to the woods, where he tearfully wonders aloud why he keeps hurting people, thinking about the people he accidentally hurt or killed over the season. He even hits himself a couple of times.
• The second-to-last scene of the episode is Castiel sitting dejectedly in the Men of Letters bunker, clearly brokenhearted by Dean's decision to host Michael and what happens afterward.

Season 14

14x05 - Nightmare Logic

• Bobby being forced to confront an illusion of his deceased son, Daniel. To make matters worse, Daniel taunts him for inadvertently causing his death. The encounter sends Bobby into a BSOD, leading to his decision to take a temporary sabbatical from hunting alongside Mary.

14x06 - Optimism

• Charlie telling Sam about Kara, her girlfriend who died in the Apocalypse World.

14x07 - Unhuman Nature

• Dean's sort-of parting trip with Jack is heartwarming, but as Castiel bluntly notes, Dean never forgives himself for not trusting Jack the first time they met, having considered him a honorary son, and wants to make it up by all means. It become sadder when the episode ends with Rowena announcing that Jack's illness is terminal.

14x08 - Byzantium

• Jack's death. What is worse, only Sam is there for his final moments. Dean, Sam, Castiel go to a bar to drown their sorrows. By the time they realize they can never accept his death, they start working to find a way to bring him back.
• Jack's reunion with Kelly ends on a sad note once Kelly realizes that Jack being in Heaven means that her son is dead.
• Lily Sunder's reaction when Anubis tells her that she is going to Hell upon death, separating her from May, and there is nothing he can do to change it. Thankfully, Lily's Heroic Sacrifice to resurrect Jack by the end of the episode tips the balance in her favor, allowing her to enter Heaven.

14x12 - Prophet and Loss

• Nick's rejection to accept Sarah over Lucifer, saying that he has gone too far now. He can only apologize to her before walking away, essentially denying his wife afterlife.
• Sam's breakdown when Dean appears unmoved from his suicidal plan to defeat Michael. He drunkenly attacks Dean, all while sobbing, until Dean finally relents and changes his mind.

14x13 - Lebanon

• Sam has his first face-to-face talk with (present-day) John in more than 12 years. Since John came from 2003, his last memory of Sam is their messy fight before Sam decided to storm off for Stanford. As for Sam, his last memory is also their messy fight, but not that one. It was the one they had in the hospital where Dean was treated after the car crash in the Season 2 premiere. The one where John died, leaving Sam with a long-lasting guilt until today.
• When John hears Mary's voice, his face just crumples, as twenty years of pain and loss rush through him. The way he says her name before he even sees her is just filled with almost-terrified hope, before at last he sees her and she sees him and they fall into each other's arms, no questions asked.
• Because the timeline has been altered for the worse, John must return to his time. He has a tearful sendoff with Dean, Sam, and Mary before returning and finding himself waking up in the Impala, thinking that everything that happened was a good, but mere dream.

14x18 - Absence

• It's confirmed that Jack accidentally killed Mary. Meaning Dean and Sam have lost their mother again. The best that can be said about the situation is that, unlike Mary's first death 36 years ago, she died painlessly and her soul is in Heaven, where she has been reunited with John, her soul mate.
  • All members of Team Free Will have flashbacks to happier times with Mary, just to prove that she is an equally motherly figure to all of them.
  • Jack doesn't accept the fact that he caused Mary's death and runs away for the whole episode. Essentially, he is faced with two prospects: keep running away, or return and possibly face the Winchesters' wrath.
  • Even Rowena is saddened. She does not tell the brothers and Castiel explicitly that Mary died, just that "she is not in this world". Later, she attempts to dissuade Jack from performing the resurrection spell, stating that he would not like the results.
  • At the end, Jack completes the resurrection spell, but all he does is bringing back Mary's dead body. He runs away again just as the brothers arrive and see their mother's dead body lying on the ground. They have no choice but to give her a hunter's funeral.

14x19 - Jack in the Box

• Dean privately sobbing to Mary's death in the opening.
• Jack's reaction when he sees Castiel in Heaven: "I'm making angels." He sounds so proud and clearly expects Castiel to be happy as well. Even without out a soul, all he's trying to do is make one of his surrogate fathers happy and proud.
• Sam lying to Jack, on Dean's instructions, in order to trick him into climbing into the Mal'ak box. He's visibly struggling to keep a straight face as he deceives Jack.

14x20 - Moriah

• The Reveal that Chuck/God is Evil All Along. Everything Dean, Sam, Castiel, and all of their allies did, hell everything that the angels, demons, ghosts, Leviathans, and countless other beings did, it's all for naught. God always treats them as expendable, and he will never see them as anything better than that.
• Jack's second death. At the hands of Chuck AKA his own grandfather, no less.
• Jack telling Dean that he understands that he's become a monster and accepting his death when Dean has him at gunpoint. Dean is visibly troubled by this.
• Before his death, Jack went to visit his birth mother Kelly's parents to try to make himself happy, since he lost his soul. But he only met his grandmother who confronts him for lying; after Jack's first visit in "God and Monsters", the grandparents called Kelly's workplace to learn that no one's heard of Jack and that Kelly's missing (unaware that she's dead). His grandmother angrily demanding to know what happened to her, caused Jack's eyes to glow and shout "Stop!". He didn't kill her like he accidentally killed Mary. Instead, he just walked away upon seeing her so afraid of him. Jack admits to Castiel he didn't feel anything at that moment, even though he knew he should.
• Even though Dean's been wanting to kill Jack for the last three episodes, when he finally has him at gunpoint, he can't pull the trigger. Because he knows that Mary wouldn't want this.

Season 15

15x4 - Atomic Monsters

• After everything they've been through over the years, even with Chuck out of the way for the time being, Sam reveals to Dean just how emotionally exhausted he's become.
  Dean: We are finally free to… move on, you know?
  Sam: I don’t know. Uh… I don’t know if I can move on. You know, I... I can’t forget about any of them. Dean, I still think about Jessica. I… I can’t just let that go.
  Dean: No, man, that’s not what I’m talking about.
  Sam: I know, I know, I know. I’m sorry. I know. But… but what I’m saying is that I don’t feel "free". What we’ve done, what we’ve lost, right now, that is what I’m feeling, and… and sometimes it’s… it’s like I-I can’t even breathe. But maybe tomorrow. You know, maybe I’ll… I’ll feel better in the morning.
  Dean: And what if you don’t?
  Sam: I don’t know.

15x7 - Last Call

• Dean ends up killing his old friend Lee Webb, for sacrificing countless victims to a monster he captured called a marid, in exchange for health and wealth. Dean was left completely speechless for what he was forced to do.

15x18 - Despair

• The episode's ending. Trapped in a room with Billie outside, Cas finally tells Dean about his deal to save Jack. Then, after 11 years of subtext, he chokes out a love confession to summon The Shadow. Cas is in tears for most of it, and the Shadow appearing gets Dean to break down himself. The final shot of the episode is him ignoring a call from Sam and burying his head in his hands.
  • To make things worse, listen to Dean as the episode ends. He is audibly sobbing over what just happened. Whether you believe Cas' feelings for him are mutual or not, Dean is truly broken.

15X17 - Unity

• Amara's meeting with Jack. She laments not meeting him before and hoped to start a relationship with her grandnephew. Considering what happens from this episode onwards, they never had the chance.

15X19 - Inherit The Earth

• Dean, Sam, and Jack's reactions to finding out they're the only living things left on Earth are one of disbelief and hopelessness. Even worse, when they try to bargain with Chuck that they will go along with his story, he spitefully states that he will simply leave them alone on an empty world, spending the last moments in shame.
• When Dean finds a dog Chuck missed, he's overjoyed and names the dog Miracle, clearly intending to adopt the dog. Then Chuck semi-literally kicks the dog by disintegrating Miracle to deny Dean even that bit of happiness.
• In a way, Michael's death. While he did betray the Winchesters (which they were counting on), it's tragic and pitiful seeing this dutiful son, who has spent eons carrying out his father's plan even after God left being killed by his own father out of spite, all because Chuck couldn't forgive Michael for initially siding with the Winchesters.

15x20 - Carry On

• We begin with the most gut-wrenching moment in the show — The final death of Dean Winchester.
  • What hurts the most is how relatively normal it was. Dean was impaled on a faulty piece of rebar in the middle of a fight with some vampires. It's a far cry from how you'd expect one of the saviors of the universe to go out.
  • To add to the waterworks, Sam and Dean's last interaction is a perfect mirror of the pilot.
    Sam: You, don't leave me. Don't leave me. I can't do this alone...
    Dean Yes, you can.
    Sam: Well, I don't want to.
    • Speaking of the pilot, Dean admits to Sam that when he first came to see him that night, he's been standing outside Sam's dorm for hours. Dean was afraid Sam doesn't want to see him, because he didn't know if he could go on hunting without him.
  • "I did not think this would be the day. But it is. It is, and that's... That's okay."
• The montage of Sam living alone in the bunker with only Miracle, further emphasizing that Dean is really gone. All while "Brothers in Arms" by Dire Straits plays in the background, which really sets the mood.
  Sam: (comforting Miracle) I miss him too.
• The Leoni version of the theme plays in the series finale, as Sam dies and meets Dean in Heaven.

Other

• The very sound of "Carry On Wayward Son" by Kansas has been known to make some long time viewers teary-eyed. This might have something to do with the show's history with season finales.
  • The Leoni version of the theme plays in the series finale, as Sam dies and meets Dean in heaven.
• The anime version of "What Is and What Should Never Be". Arguably worse than its live-action counterpart due to the fact that Anime!Dean is portrayed as being more expressive with his emotions and is that much happier about having his wish granted. When he realizes what's going on, he apologizes to his family, who get increasingly freaked-out and worried by his speech, before stabbing himself to death in front of them and waking up in the real world.