The look on Sam's face in the pilot when he opens his eyes to see Jess on the ceiling, stomach sliced open, for an instant 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.
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. (He hangs up sadly, with tears in his eyes.)
In retrospect, after watching season 4 premiere and beyond, there is one line in "Faith" 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 "Faith", in which the boys are forced to stop a reaper controlled by the faith healer'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.
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: (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.) Without you and Dad... (Sam turns away from Dean.)
From the same episode, John's old friends are being killed by demons and he finally snaps when Sam questions him one too many times: "I want to stop losing people we love. I want you (Sam) 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."
After all Sam and Dean's issues with John in the first season:
Dean: Daddy, please...
Another from "Devil's Trap," how Dean realizes that John is possessed by the demon - 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.
The last ten minutes of "In My Time of Dying".
"Children Shouldn't Play With Dead Things":
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.) So, tell me... what could you possibly say to make that all right? (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.)
"Houses of the Holy":
Dean: I'm tired, Sam. I'm tired of this job, this life. This weight on my shoulders, man, I'm tired of it.
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.
When Dean explains why he doesn't believe.
Dean: Okay, all right. You know what? I get it. Youíve got faith. Hey, good for you. Iím sure it makes things easier. Iíll tell you who else had faith like that Ė- Mom. She used to tell me when sheíd 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: Whatís to tell? She was wrong. There was nothing protecting her. Thereís no higher power, thereís no God. Thereís 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? Iím gonna need to see some hard proof. You got any?
When you know she was right and how much worse that makes everything...
"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..."
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, 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.
"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.
The end of "Heart". 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.
"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.
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.
"All Hell Breaks Loose":
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.
The ending conversation in "All Hell Breaks Loose" just broke her 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.
Dean: 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?
Also Bobby: "Are you that screwed in the head?!" Yes, Bobby, yes he is.
Dean's just sold his soul and only has a year to live, but he begs Bobby not to tell Sam... *sniffle*
Daddy Winchester crawling out of Hell to save his two 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.
Then there's the moment where 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!"
"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.
"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 end of Sam's argument with Dean. "I wish you'd drop the show and be my brother again. 'Cos... Just 'cos."
The sobbing, desperate Sam holding Dean's body in his arms when Dean dies "for real" in "Mystery Spot" The first half of that episode was unexceptional; the second half, between that moment and Sam majorly Taking A Level In Badass (pulling a bullet out of your own chest? Seriously, that is awesome. It kind of completely rocked).
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."
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.
The moments where Dean was so close to having a complete nervous breakdown in "Long-Distance Caller" where he was so desperate to believe that Daddy would save him from hell.
I can't help but feel sorry for Mr. Benton, who 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 (by 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 monsterous 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!
"No Rest for the Wicked": Dean dies in front of Sam's eyes, right after convincing Sam not to use his powers to save him. Sam cradles his body, 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 pre-emptiveReally 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.
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?
And that's not counting the reunion scenes... the hugs... the returning of the amulet...
From "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?
"In the Beginning" 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.
"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.
"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.
"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...
Sam's flashbacks in "I Know What You Did Last Summer" revealing just how much of a mess he was after Dean's death.
"Heaven and Hell". Dean's breakdown, one of the most powerful scenes in the entire show. Dean admits 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 asked a question, if he would get off the rack and take up the torture himself. Jensen Ackles' voice is dead, as if he's trying so damn hard to keep himself from breaking down, and 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, and 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 when Dean admits that he feels empty inside and wishes that he couldn't feel anything, you are going to be crying along with him.
"Criss Angel is a Douchebag". The final line from Jay: "Throw them away."
In "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.
"Sex and Violence": The brothers exchanging hurtful words and even when they say everything's cool between them, it's not.
Pamela slowly dying at the end of "Death Takes a Holiday". Her voice breaks when she tells the guilt-ridden Winchester boys, "I told you I didn't want anything to do with this!"
"On the Head of a Pin". Uriel turns out to be a traitor and has to be killed and Dean gets broken completely (this is the end of the hell-revelations, right, writers? Right?) having to learn that John apparently never broke, Dean was the first seal and that he's the only one who can stop the apocalypse—then rewatch it knowing he was never intended to stop the apocalypse, only to raze the world stopping Lucifer.
"Jump the Shark". Sam getting to play big brother for a change. Dean refusing to believe it, and then his face when he sees 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."
"The Rapture", from beginning to end, is a masterpiece and a work of art 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. Once Cas is back in Jimmy, he simply gets up, exchanges one look with Jimmy's wife, and continues to walk away. "It doesn't matter. You take me. You take me."
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, 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.
"When the Levee Breaks." Everything about it, 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 heartwrenching.
The looks on both Castiel and Anna's faces when he is forced to betray her by turning her over to other angels.
Ruby. 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 (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!
The brothers splitting up in "Good God, Y'all", full stop. Even when they fight, they're still all the family they have, and seeing them separate is so very wrong.
Sam and "Jess", AKA Lucifer,'s scenes together in "Free to Be You and Me". 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 in "Free to Be You and Me" 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.
"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 Crowning Momentof Heartwarming, but also a Tear Jerker.
Made worse after watching the rest of the season. 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.
"Changing Channels" 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.
"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. Then 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.
In "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.
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.
"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."
"Dead Men Don't Wear Plaid":
Bobby: She was the love of my life. How many times do I have to kill her?
Again, heartbreaking because of real-life: Jim Beaver is in fact a widower.
"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.
Hunter: You just snuffed his brother. Do you really want Dean Winchester on your ass for the rest of your life?
The fierce look on Dean's face is heartwrenching.
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.
"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 wretching 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.
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.
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.
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).
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 Luciferís pleas. Heís just as sad as Lucifer, but he is a soldier first and he has a duty to his father.
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."
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.]
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.
On a lighter (?) note, Misha in "The French Mistake" actually being killed. 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.
"And Then There Were None" - Rufus' funeral. But averted with Samuel's death, since he was an asshole.
The ending of "My Heart Will Go On," and the boys deciding not to tell Bobby about the alternate timeline where he was married to a still-living Ellen and happy.
In "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.
The entire conversation between Dean and Cas in "Let It Bleed" 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.
In "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 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 him, 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. Funny, Castiel who was learning sarcasm tips into the deep end, becoming the thing he was against. YMMV, though, as the rest of us thought this was awesome.
It was mainly a tearjerker because a lot of Cas fans saw 'something' heading towards him snapping. The continuous poor treatment Castiel 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.
Another reason it's gutwrenching is because the Winchesters are being hypocritical at this point: Throughout the series, when have they ever not been willing to cross a line to save someone/solve a problem/procure personal power? Even with lives on the line, even if they had to go behind each other's backs, they've always been ready, when push came to shove, to take the risk - and the worst part is that it ends up fine in the end, more or less, and they always end up forgiving each other because they're family. Conversely, Cas is treated many times as if his only worth is in being a powerful ally, and is mocked relentlessly not just by the monsters but by Dean whenever he's low on power ("baby in a trenchcoat", anyone?) And yet suddenly, when he tries to apply the things they taught him and do the exact same thing (deal with a monster, absorb the power of Purgatory), they condemn him for it without even hearing the details or offering an alternate plan and resort to trying to kill him in pretty short order, in spite of the allegations that he's family. Which makes it understandable why he proclaims that they're not his family, in the end - from his point-of-view, they must have been lying about it, otherwise they would've given him the same break they always give each other in such situations.
Tortured!Sam begging normal!Sam to stay in the coma rather than take the memories of 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.
In the premiere, "Meet The New Boss", 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?
What about 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.
Dean picking up Castiel's trenchcoat in "Hello Cruel World".
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 he always is." Made even more heartbreaking because at the end of the episode, he'snotthere.
The last scene with Jo in "Defending Your Life." 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.
"Slash Fiction": Sam finally finds out Dean killed Kitsune Amy Pond and confronts him. After all the time he tried to get Dean to talk to him, Sam doesn't want to hear it.
"Season Seven, Time For A Wedding": The nicest thing anyone's ever said to Garth is "You don't suck."
In "Death's Door" the ending where Bobby sacrifices what's left of his brain to pass on the knowledge he got 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. "They never thank you."
Dean's denial is what gets me every time. Sam is trying to be realistic and pragmatic and can absorb what the doctors try to tell them, that he probably won't make it. 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 asked him if he was going to stay or go he just looked 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.
"Plucky Pennywhistle's Magical Menagerie": The fun, 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.
YMMV, but Emma's death in "Slice Girls" could be seen as tragic. The look on Dean's face as she bleeds out from Sam's gunshot seems to indicate he truly wanted to save his daughter.
"Time After Time" has Sheriff Mills 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.
"The Born Again Identity". Everything from Sam's deteriorating mental state to Dean's conversations with Emmanuel (Castiel with amnesia) to Castiel taking Sam's insanity onto himself at the end. The entire episode seemed designed to make fans weep.
"Party on Garth" has in its final two minutes Bobby finally returning as a ghost, and trying in vain to get Dean to notice him
YMMV obviously, but the alpha vampire's reaction to Edgar coldly telling him that they will kill him and all his "children" in "There Will Be Blood". 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...
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.
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.
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.
The end of "What's Up, Tiger Mommy?" caused a collective scream of anguish from the fans. Just after Kevin 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), Dean nonchalantly dismisses it as just another nightmare. Cut to Cas screaming for Dean and reaching out to him during what is assumed to be his escape from Purgatory.
A "A Little Slice of Kevin" 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.
Despite Hunteri Heroici being a mostly lighthearted episode, 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 from the same episode. He had invested everything in 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...
The entirety of Samandriel's character in general is heartbreaking. When we meet him, he is one of the most adorable, 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 Torn and Frayed. 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.
Dean breaking off all contact with Benny, especially since Benny had asked Dean to help him through a low point.
Henry learns in "As Time Goes By" that there is nothing left of the secret order he trained his whole life to be part of, and that his son 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 the brothers and with the way things are.
Dean's admission in "Trial And Error" 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.
Dean's prayer to Castiel at the end of "Remember the Titans":
Dean:Cas, you got your ears on? Listen, you know Iím not one for praying ícause in my book itís the saĖ itís 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 donít know whatís ahead or what itís going to bring for Sam. Now heís covering pretty good, but I know that he is hurtiní. And this one was supposed to be on me. So for what weíve been through, [he closes his eyes, pauses for a moment] Iím asking you, you keep a lookout for my little brother, okay? [he stops, looks around] Where the hell are you, man?
Especially 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.
Dean pleading with Castiel to overcome his apparent mind control near the end of "Goodbye Stranger."
"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.
Goodbye Stranger: Meg Masters, fullstop. 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 having given him up to Purgatory. She also appears to have developed some sort of attachment to Castiel, even drawing connections between him and Sam's ex, Amelia Richardson. And at the very end, Crowley kills her right in front of the Winchesters, who only watch and escape.
"Take care of my Unicorn."
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 realise 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 favour 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 Dean's rather cruel breaking of their friendship to save a guy who would kill Benny just for existing. Now that is a friend.
Clipshow 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 superpowerful enemy that we have no chance of defeating, but we have to," type of prefinale 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.
Cas 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 who's 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.
Dean not accepting Cas' apology. Just the looks on their faces...
In "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.
Of course, Crowley could have just as easily been faking the whole thing, but we'll have to wait until next season to find out.
... really? We're just going to ignore a certain conversation near 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.
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 justĖ
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.
Castiel's (brief) death and his reaction to Dean telling him to leave. Cas' large Puppy-Dog Eyes just make it worse.
Dean's reaction to thinking his best friend was dead, especially the little sob in his voice when he yelled "Cas!"
Cas starts singing Walking on Air to comfort the crying daughter of his coworker. 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..."
In that same episode, Cas's face when he realizes that he doesn't have a date—he's just been asked to babysit.
The last half of "Holy Terror". It all goes downhill when Kevin snaps at Dean by saying everytime 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 and kills Kevin and telling Dean that Sam was gone. The episode's final scene also drives it home. Dean sitting on the floor, crying and just repeating Kevin's name.
The beginning of "Road Trip" manages to top the above example 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) and then angrily throws the stuff around.
The end of "First Born" when Dean has been given the Mark of Cain and Crowley tells him;
Crowley: Your problem, mate, is that nobody hates you more than you do. Believe me, I've tried.
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.
Dean's speech to Ghost Kevin apologizing for causing his death, and at the end being forgiven for it.
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...
Another moment in this episode? 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 he's dead.
YMMV, but consider. 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.
Despite the base breaker status the breakup of the Ghostfacers in "Thinman" can be seen as a downer given that is mirrors Sam and Dean's recent estrangement and, unlike Sam and Dean, they might not reconcile.
Or rather, like Sam and Dean.
"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 is 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.
Episode 10.1 - "Black"
Seeing how far Sam has gone in his quest to find Dean is heartbreaking. Torturing demons, driving himself into the groiund, and going on even with a broken arm.
Castiel's state since the defeat of Metatron. 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.
Bit of a meta one here but 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.
Episode 2 - "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 Winchester;
Sam: I donít 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: Donít 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 behaviour 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 could'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.
Episode 3 - "Soul Survivor"
Deanmon's Not So Different 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 Winchester in blaming him for turning both Dean and Sam into hunters just drives home how messed up both Winchesters actually are.
Episode 5 - "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'd clearly forgotten up until this point that Adam even existed.
The entire "Carry On My Wayward Son" song brought tears to this troper's eyes. Especially since the most important parts were sung by someone who was supposed to be Mary, their departed mother. It was like their mother was telling them to carry on, because once they're done, they'll finally have peace.
Also, 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 tells you he likes something you did, you know that you aren't a joke, no matter what other people say.
Episode 6 - "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.
Episode 7 - "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 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 Novak 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 in Episode 5;
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, and Dean's face clearly says that he wasn't;
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.
Episode 9 - "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.
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 who 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.
The very sound of "Carry on my 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 anime version of "What Is and What Should Never Be". Arguably worse than its live-action counterpart because 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.