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[[AC:1x06 - Skin]]
* 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 [[BreakThemByTalking 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 [[IJustWantToBeLoved 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.
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[[AC: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.
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* 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.

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* 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.
mistake, leaving behind her father who, according to Tessa, doesn't really have any family left.
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The situation is more complex than this. Castiel was willing to farm souls by altering the future to win the war; his plan relying on manipulating the others and leaving out critical information made things worse and worse.


** 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.
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* [[spoiler:The montage of Sam living alone in the bunker with only Miracle, further emphasizing that Dean is really gone. All while "[[https://www.youtube.com/watch?v=7dBRQvXe91g Brothers in Arms]]" by Music/DireStraits plays in the background.]]

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* [[spoiler:The montage of Sam living alone in the bunker with only Miracle, further emphasizing that Dean is really gone. All while "[[https://www.youtube.com/watch?v=7dBRQvXe91g Brothers in Arms]]" by Music/DireStraits plays in the background.background, which really sets the mood.]]

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* The [[https://www.youtube.com/watch?v=qKvj12YTtI4 Leoni version of the theme]] plays in the series finale, as Sam dies and meets Dean in heaven.

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* [[spoiler:The montage of Sam living alone in the bunker with only Miracle, further emphasizing that Dean is really gone. All while "[[https://www.youtube.com/watch?v=7dBRQvXe91g Brothers in Arms]]" by Music/DireStraits plays in the background.]]
-->'''Sam:''' [[spoiler:''(comforting Miracle)'' I miss him too.]]
* The [[https://www.youtube.com/watch?v=qKvj12YTtI4 Leoni version of the theme]] plays in the series finale, as Sam dies and meets Dean in heaven.Heaven.
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--> '''Sam:''' [[PleaseDontLeaveMe You, don't leave me.]] ''[[PleaseDontLeaveMe Don't leave me.]]'' I can't do this alone...\\

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--> ---> '''Sam:''' [[PleaseDontLeaveMe You, don't leave me.]] ''[[PleaseDontLeaveMe Don't leave me.]]'' I can't do this alone...\\



*** 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 [[ICantDoThisByMyself if he could go on hunting without Sam]].

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*** 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 [[ICantDoThisByMyself if he could go on hunting without Sam]].him]].

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*** 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 [[ICantDoThisByMyself if he could go on hunting without Sam]].



** Dean admits to Sam that when he first came to see him in the [[Recap/SupernaturalS15E20CarryOn first episode]], he's been standing outside Sam's dorm for hours, because he was afraid Sam doesn't want to see him.
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** 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.

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** To make things worse, listen to Dean as the episode ends. He is audibly sobbing over what just happened. Whether you believe Cas’ Cas' feelings for him are mutual or not, Dean is truly broken.



** Dean admits that when he first came to see Sam in the [[Recap/SupernaturalS15E20CarryOn first episode]], he’s been standing outside his dorm for hours, because he was afraid Sam doesn’t want to see him.

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** Dean admits to Sam that when he first came to see Sam him in the [[Recap/SupernaturalS15E20CarryOn first episode]], he’s he's been standing outside his Sam's dorm for hours, because he was afraid Sam doesn’t doesn't want to see him.
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** Dean admits that when he first came to see Sam in the first episode, he’s been standing outside his dorm for hours, because he was afraid Sam doesn’t want to see him.

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** Dean admits that when he first came to see Sam in the [[Recap/SupernaturalS15E20CarryOn first episode, episode]], he’s been standing outside his dorm for hours, because he was afraid Sam doesn’t want to see him.
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** Dean admits that when he first came to see Sam in the first episode, he’s been standing outside his dorm for hours, because he was afraid Sam doesn’t want to see him.
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They didn't.


** 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 (only the next two episodes will tell), Dean is truly broken.

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** 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 (only the next two episodes will tell), not, Dean is truly broken.
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to:

* 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.
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* The Leoni version of the theme plays in the series finale, as Sam dies and meets Dean in heaven.

to:

* The [[https://www.youtube.com/watch?v=qKvj12YTtI4 Leoni version of the theme theme]] plays in the series finale, as Sam dies and meets Dean in heaven.
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* The Leoni version of the theme plays in the series finale, as Sam dies and meets Dean in heaven.


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** The Leoni version of the theme plays in the series finale, as Sam dies and meets Dean in heaven.

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* 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 confront 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 "[[BigShutUp 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.

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* 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 confront 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 "[[BigShutUp Stop!]]". He didn't kill her like he accidentally killed Mary, instead 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.



--> '''Sam:''' [[PleaseDontLeaveMe Don't leave me.]] ''[[PleaseDontLeaveMe Don't leave me.]]''. I can't do this alone...\\

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--> '''Sam:''' [[PleaseDontLeaveMe Don't You, don't leave me.]] ''[[PleaseDontLeaveMe Don't leave me.]]''. ]]'' I can't do this alone...\\



** ''"I did not think this would be the day. But it is. It is, and that's... That's okay."''



* 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 [[DownerEnding season finales]].
* [[Anime/{{Supernatural}} 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.

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* The very sound of "Carry On Wayward Son" by Kansas has been known to make some long time viewers teary eyed.teary-eyed. This might have something to do with the show's history with [[DownerEnding season finales]].
* [[Anime/{{Supernatural}} The anime version]] of "What Is and What Should Never Be". Arguably worse than its live-action counterpart because 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.
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** To add to the waterworks, [[spoiler: Sam and Dean's]] last interaction is a perfect mirror of the pilot.
--> '''Sam:''' [[PleaseDontLeaveMe Don't leave me.]] ''[[PleaseDontLeaveMe Don't leave me.]]''. I can't do this alone...\\
'''[[spoiler: Dean]]''' Yes, you can.\\
'''Sam:''' Well, I don't want to.
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-->--'''Music/{{Kansas}}''', "Carry On Wayward Son"

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-->--'''Music/{{Kansas}}''', -->-- '''Music/{{Kansas}}''', "Carry On Wayward Son"
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->''On a stormy sea of moving emotion''
->''Tossed about, I'm like a ship on the ocean''
-->--'''Kansas, "Wayward Son"'''

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->''On ->''♫ On a stormy sea of moving emotion''
->''Tossed
emotion\\
Tossed
about, I'm like a ship on the ocean''
-->--'''Kansas, "Wayward Son"'''
ocean. ♫''
-->--'''Music/{{Kansas}}''', "Carry On Wayward Son"



--> '''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]''

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--> '''Dean''': '''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]''
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[[AC:15x20 - Carry On]]
* We begin with the most gut-wrenching moment in the show -- [[spoiler: The final death of Dean Winchester.]]
** What hurts the most is how relatively ''normal'' it was. [[spoiler: 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 [[spoiler: one of the saviors of the universe]] to go out.
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** To make things worse, listen to Dean as the episode ends. He is audibly sobbing over what just happened. Whether you believe his feeling for Cas is mutual or not (only the next two episodes will tell), Dean is truly broken.

to:

** To make things worse, listen to Dean as the episode ends. He is audibly sobbing over what just happened. Whether you believe his feeling Cas’ feelings for Cas is him are mutual or not (only the next two episodes will tell), Dean is truly broken.
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** To make things worse, listen to Dean as the episode ends. He is audibly sobbing over what just happened. Whether you believe his feeling for Cas is mutual or not (only the next two episodes will tell), Dean is truly broken.
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[[AC:15x18 - Despair]]
* The episode's ending. Trapped in a room with Billie outside, Cas finally tells Dean about his deal to save Jack. Then, [[HoYay after 11 years of subtext,]] he chokes out a love confession to [[KilledOffForReal 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.
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* Before his death, Jack went to see his human grandparents to try to make himself happy, as he was losing his soul. But he only met his grandmother who accuse him of killing her daughter; after Jack left in his first visit, the grandparents call their daughter's workplace to learn that she's missing. His distraught grandmother screams at Jack, demanding to know what he's done to her, but Jack's eyes glow red and shout "[[BigShutUp 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.

to:

* Before his death, Jack went to see visit his human grandparents birth mother Kelly's parents to try to make himself happy, as since he was losing lost his soul. But he only met his grandmother who accuse confront him of killing her daughter; for lying; after Jack left in his Jack's first visit, visit in "God and Monsters", the grandparents call their daughter's called Kelly's workplace to learn that no one's heard of Jack and that Kelly's missing (unaware that she's missing. dead). His distraught grandmother screams at Jack, angrily demanding to know what he's done happened to her, but caused Jack's eyes to glow red and shout "[[BigShutUp 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.
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[[folder: Season5]]

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[[folder: Season5]][[folder:Season 15]]
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* Before his death, Jack went to see his human grandparents to try to make himself happy, as he was losing his soul. But he only met his grandmother who accuse him of killing her daughter; after Jack left in his first visit, the grandparents call their daughter's workplace to learn that she's missing. His distraught grandmother screams at Jack, demanding to know what he's done to her, but Jack's eyes glow red and shout "[[BigShutUp 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.


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[[folder: Season5]]
[[AC:15x7 - Last Call]]
* [[spoiler: 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.]]
[[/folder]]
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dewicking


* [[PapaWolf John]] [[LikeABadassOutOfHell crawling out of Hell]] [[NotTooDeadToSaveTheDay to save his sons again]]. Then any composure is gone with the exchange:

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* [[PapaWolf John]] [[LikeABadassOutOfHell [[EscapedFromHell crawling out of Hell]] [[NotTooDeadToSaveTheDay to save his sons again]]. Then any composure is gone with the exchange:
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---> '''Fake!Sam''': Why is it our job to save everyone? Haven't we done enough?

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---> '''Fake!Sam''': -->'''Fake!Sam''': Why is it our job to save everyone? Haven't we done enough?
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--> '''Dean''': I'm tired, Sam. I'm tired of this job, this life. This weight on my shoulders, man, I'm tired of it.

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--> '''Dean''': -->'''Dean''': I'm tired, Sam. I'm tired of this job, this life. This weight on my shoulders, man, I'm tired of it.
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--->'''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?

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--->'''Sam:''' -->'''Sam:''' You never told me that.
--->'''Dean:''' -->'''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?

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