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* EvenEvilHasStandards: Implied. The Trickster may be perfectly comfortable with torturing Sam by forcing him to watch Dean die over and over again as his endgame is to make sure Sam accepts the fact that his relationship with Dean will not end well, but when Sam is willing to go as far as to kill Bobby just because he believes he is the Trickster and makes it clear he will go as far as to kill a person for no other reason than to find the Trickster, the Trickster ''finally'' decides to stop playing around. Considering the fact that he claims most of the people he's hurt as a Trickster got what they deserved, it shows while he won't hesitate to put someone through a lot of pain or, in case for assholes, kill them, he is not comfortable with killing innocents.
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* TookALevelInJerkass: In his previous appearance, The Trickster punishes the high and mighty in a way that can be cruel but in this episode, his torture of Sam is exceptionally vicious from a psychological perspective.
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* TookALevelInJerkass: In his previous appearance, The Trickster punishes the high and mighty in a way that can be cruel cruel, but in this episode, his torture of Sam is exceptionally vicious from a psychological perspective. Subverted as the Trickster reveals that this was actually him trying to prepare Sam for Dean's inevitable death.
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Up To Eleven is a defunct trope
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* TheyKilledKennyAgain: Taken UpToEleven.
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*** The former could easily be explained. The Waitress accidently shot and killed Dean.
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Dewicking per TRS.
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* ContinuityNod: To draw more parallels between [[NotSoDifferent Sam and John]]. After Dean dies on Wednesday, Sam outfits the trunk of the Impala with the same weapons case John had in [[Recap/SupernaturalS01E20DeadMansBlood "Dead Man's Blood" (S01, E20)]].
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* ContinuityNod: To draw more parallels between [[NotSoDifferent [[MirrorCharacter Sam and John]]. After Dean dies on Wednesday, Sam outfits the trunk of the Impala with the same weapons case John had in [[Recap/SupernaturalS01E20DeadMansBlood "Dead Man's Blood" (S01, E20)]].
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* TookALevelInJerkass: In his previous appearance, The Trickster punishes the high and mighty in a way that can be cruel but in this episode, his torture of Sam is exceptionally vicious from a psychological perspective.
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* HopeSpot: After confronting the Trickster at stake point he transports Sam and Dean to Wednesday seemingly breaking Dean's death loop. Then Dean is shot in a stickup gone wrong and Sam ''ins't'' send back to his time loop. Sam then spends the next six months without Dean.
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* HopeSpot: After confronting the Trickster at stake point he transports Sam and Dean to Wednesday seemingly breaking Dean's death loop. Then Dean is shot in a stickup gone wrong and Sam ''ins't'' send ''isn't'' sent back to his time loop. Sam then spends the next six months without Dean.
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%%Is this In-universe? * SuspiciouslyAproposMusic: On the second Wednesday, Sam wakes up to Music/HueyLewisAndTheNews' "Back in Time".
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* AndIMustScream: The Trickster, when confronted, explains that while killing off Dean over and over again is fun, it's meant to target Sam first and foremost and not his brother. Specififcally, being stuck in an [[GroundhogDayLoop infinite loop]], forced to watch his brother die without being able to stop it.
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* AndIMustScream: The Trickster, when confronted, explains that while killing off Dean over and over again is fun, it's meant to target Sam first and foremost and not his brother. Specififcally, Specifically, being stuck in an [[GroundhogDayLoop infinite loop]], forced to watch his brother die without being able to stop it.
* BlackComedy: While the first two, and the last, of Dean's deaths are genuinely sad and traumatic the various deaths in between are pretty hilarious especially once the DeathMontage starts.
* CruelToBeKind: The lesson the Trickster is trying to impart to Sam is that his obsession with trying to save Dean is going to get him killed and that, like it or not, Dean ''is'' going to die, whether by the Trickster or by his deal, and Sam will have to learn to live without his brother.
* HopeSpot: After confronting the Trickster at stake point he transports Sam and Dean to Wednesday seemingly breaking Dean's death loop. Then Dean is shot in a stickup gone wrong and Sam ''ins't'' send back to his time loop. Sam then spends the next six months without Dean.
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* NecroNonSequitur: Some of the ways Dean dies get rather silly and improbable.
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* MoodWhiplash: And how.
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* MoodWhiplash: And how. The first two times Dean dies it's genuinely gut wrenching especially for poor Sam. Then Dean gets a pretty hilarious DeathMontage showcasing all of Dean's [[UndignifiedDeath less then dignified deaths.]] Then the episode goes right back to tragic when Dean gets shot after the skip to Wednesday and he stays dead for six months and the toll it takes on Sam once he's forced to live without his brother.
* NecroNonSequitur: Some of the ways Dean dies get rather silly and improbable.
* NecroNonSequitur: Some of the ways Dean dies get rather silly and improbable.
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*** Perhaps he doesn't die. If we see nothing, that might mean that the Trickster just reset the day immediately, without Dean dying as usual.
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* TimeLoopFatigue: Sam suffers this after the loop forces him to watch his brother die over and over again in increasingly strange ways. What's worse is that Sam is never able to stop his brother's death.
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* SuspiciouslyAproposMusic: On the second Wednesday, Sam wakes up to Music/HueyLewisAndTheNews' "Back in Time".
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%%Is this In-universe? * SuspiciouslyAproposMusic: On the second Wednesday, Sam wakes up to Music/HueyLewisAndTheNews' "Back in Time".
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* {{Irony}}: Daniel Hackard's disappears into a mystery spot, the very thing he debunks.
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* {{Irony}}: Daniel Hackard's Hackard disappears into a mystery spot, the very thing he debunks.
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* EverybodyLives: One of the very rare instance in the show.
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* EverybodyLives: One of the very rare instance instances in the show.
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Removed Ax Crazy trope
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* AxCrazy: Sam goes this on one of the days.
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Added Ax Crazy trope
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* AxCrazy: Sam goes this on one of the days.
