History TearJerker / SlyCooper

** In all the cutscenes depicting Sly's backstory he was shown peeking out of a closet right as his father's lifeless hand drops in front of him. ''He saw at least part of the aforementioned brutal murder.'' Sure, his parents may not have known Sly was in the closet but still! Sly is [[AngstWhatAngst remarkably well-adjusted for witnessing the violent deaths of his parents and the destruction of the one memento he had besides his father's cane]] [[HarmfulToMinors when he was only 8 years old]].

** In all the cutscenes depicting Sly's backstory he was shown peeking out of a closet right as his father's lifeless hand drops in front of him. ''He saw at least part of the aforementioned brutal murder.'' Sure, they may not have known that Sly was in the closet but still! Sly is [[AngstWhatAngst remarkably well-adjusted for witnessing the violent deaths of his parents and the destruction of the one memento he had besides his father's cane when he was only 8 years old]].

** Before he is defeated Clockwerk says "you will never rid of me". Although Clockwerk himself was not alive to witness nor plan for the event it was his body that ended up crippling Bentley for the rest of his life. Granted this would end up affecting Murray but seeing his friend never able to walk again thanks to the monster that massacred his family had to rattle Sly's cage at least a little bit.
* So many villains have tragic backstories themselves. Some are outright cruel and evil but others were either poor in childhood or ridiculed and mocked when young.

** Mz. Ruby never had any friends growing up, due to her voodoo upbringing scaring other kids away.

*** What's even more tragic is that this is [[TruthInTelevision all too realistic]]. Many RealLife criminals have had terrible childhoods themselves.

** Jean Bison tried to strike it rich during the Gold Rush of 1852 but wound up [[HumanPopsicle flash-frozen]] in an avalanche, waking up 150 years later. All he wants is to tame the wilderness as men like him did back then but his way of thinking is [[ValuesDissonance highly outdated]].

* Sly's backstory. His parents were brutally murdered by the Fiendish Five, and he was sent to an orphanage. On the day he was finally going to inherit the Thievius Raccoonus. Which itself was ripped apart and taken by his parents' murderers, depriving him of even a memento (since he likely would have been allowed to keep it as it's a family heirloom).
** In all the cutscenes depicting Sly's backstory, he was shown peeking out of a closet he was hiding in right as his father's lifeless hand drops in front of him. ''He saw at least part of the aforementioned brutal murder.'' Sure, they may not have known that Sly was in the closet, but still! Sly is [[AngstWhatAngst remarkably well-adjusted, for witnessing the violent deaths of his parents and the destruction of the one memento he had besides his father's cane when he was only 8 years old]].
** What makes this even more saddening? The fact that Sly was apparently supposed to inherit the Thievius Raccoonus on his ''eighth birthday'', which means that his parents were killed on his birthday.
** Before he is killed by Sly, Clockwerk tells his foe "you will never rid of me". Although Clockwerk was not alive to witness nor plan it, it was his body that ended up crippling Bentley for the rest of his life. Granted this would end up affecting Murray more than Sly, seeing his friend never able to walk again thanks to the monster that massacred his family had to rattle Sly's cage at least a little bit.
* So many villains have tragic backstories themselves. Some are outright cruel and evil, but some were either poor in childhood or ridiculed and mocked when young.
** Don Octavio started out as a famous opera singer. But then Rock music came in and no one wanted to listen to opera anymore, except for the mafia.

*** What's even more tragic is that this is all too realistic. Many real-life criminals have had terrible childhoods themselves.
*** Made even worse by the otherwise hilarious "gentleman callers/I didn't know they was yours" gag from Sly 3, which all but outright states Muggshot's mother was a prostitute. We also see him in his childhood bedroom even as a musclebound adult at the end of his intro in Sly 1, implying he still lives with her. Taking his stated desire for respect and power alongside the fact that he's fiercely protective of his mother, it's quite likely he became the monster that he is ''because'' he saw his mother being abused and vowed to become strong enough to keep them both safe and secure.
** The Panda King wanted to impress Chinese nobles with his fireworks display, but they couldn't see past his shabby clothes and chased him away.
** Jean Bison tried to strike it rich during the Gold Rush of 1852, but wound up [[HumanPopsicle flash-frozen]] in an avalanche, waking up 150 years later. All he wants is to tame the wilderness, as men like him did back then, but the problem is his way of thinking is highly outdated.

** And even at the very end, just when Carmelita's ''finally'' ready to apologize for being so nasty, all we get is a brief scene of reconciliation... and then Sly gets {{trapped in the past}}, and Carmelita's left with nothing but the photograph of them dating that Sly used to carry around with him. [[DownerEnding Never has a sequel been needed as badly as it is now]].

* The WhereAreTheyNowEpilogue of the Cooper Ancestors as you slowly realize that sooner or later, Clockwerk is going to kill them. Saleigh's ending is the saddest. He finally retires, he gets to travel the world and relax after a long life of thieving. Then Clockwerk appears...

* The ending. Bentley goes to grab the Hate Chip that powered Clockwerk, then BAM! He becomes crippled. Murray tries his best to save him, but all Bentley can cry out is, "Pick me up! I can't walk!"

* The WhereAreTheyNowEpilogue of the Cooper Ancestors as you slowly realize that sooner or later, Clockwerk is going to kill them.

!!Meta
* During a speedrun of the first game at the 2020 Summer Games Done Quick event, Sly's voice actor Kevin Miller [[https://youtu.be/SZBYWuumVIM?t=2055 was asked what his own thoughts were on Penelope's betrayal]] in ''Thieves in Time''. After (jokingly) expressing how betrayed he felt personally about it, he followed up with this:
-->'''Kevin Miller:''' [[CryForTheDevil I think she just needs a hug. That's all. Just a nice, long hug.]]

** Earlier in this level, at the beginning of the mission "A Friend in Need," Bentley's panic when Murray is captured, along with his expressed fear in losing his friends and being alone all over again, is downright heartbreaking.

* Sly's ancestor Rioichi earned the loyalty of a shark he caught while fishing after he spared it. The shark served faithfully as his mount in war for years. After growing to old to fight and seeing that Rioichi wanted to open a sushi restaurant he asked that Rioichi kill and turn him into sushi so his master could open his restaurant. Rioichi agreed, crying as he turned his friend into his restaurant's first meal.

** Don Octavio started out as a famous opera singer. But then Rock music came in and no one wanted to listen to opera anymore.

** When Bentley finally confronts Penelope, he makes an attempt to reason with her, showing the gang will let this slide if she realizes [=LeParadox=] is only using her, and will "cut her strings" when he's done. She doesn't listen to ''any'' of his words, and shows she's well beyond the MoralEventHorizon by attacking Bentley in her VillainousBreakdown, showing that if [[DomesticAbuse she can't control him]] [[AmbitionIsEvil for all the money in the world]], [[IfICantHaveYou she'll kill him]] [[IWillPunishYourFriendForYourFailure and everyone he cares for]].

-->''Kevin Miller:'' [[SympathyForTheDevil I think she just needs a hug. That's all. Just a nice, long hug.]]

* The ending. [[spoiler:Bentley goes to grab the Hate Chip that powered Clockwerk, then BAM! He becomes crippled. Murray tries his best to save him, but all Bentley can cry out is, "Pick me up! I can't walk!"]]

* When Bentley walks into General Tsao's Palace, you hear him refuse to let his betrothed, [[spoiler: who is the Panda King's daughter, Jing King]], be released from prison just to talk to [[spoiler: her father]]. Just hearing her crying about his cruel treatment is enough to put a tear to your eye.
* The opening cutscene of the "Honor Among Thieves" chapter. Sly, [[spoiler:who believes he is going to die by some Dr. M's freaky mutant, mourns the botched Cooper Vault job and the fact he never got to see what's in the vault, thinks about his legacy and finally laments how he never took a chance with Carmelita and thinks that he would want to put their "professional differences" behind if he ever meets her again. Even though things turned out well for him in the end, those were his thoughts when he was certain he was going to die.]]

* Bentley's reaction to [[spoiler:Penelope being the Black Knight]] certainly serves as one. [[spoiler:He retreats into his shell for the remainder of the episode, until he finally comes through at the last minute to stop her from crushing Sly, earning himself a SugarWiki/MomentOfAwesome as well.]]
** When Bentley finally [[spoiler:confronts Penelope, he makes an attempt to reason with her, showing the gang will let this slide if she realizes [=LeParadox=] is only using her, and will "cut her strings" when he's done. She doesn't listen to ''any'' of his words, and shows she's well beyond the MoralEventHorizon by attacking Bentley in her VillainousBreakdown, showing that if [[DomesticAbuse she can't control him]] [[AmbitionIsEvil for all the money in the world]], [[IfICantHaveYou she'll kill him]] [[IWillPunishYourFriendForYourFailure and everyone he cares for]]]].

* If you've followed the progress of Sly and Carmelita's complicated relationship in the first three games, the events of ''Thieves in Time'' are particularly painful to watch: Carmelita, angry at Sly [[spoiler: because he faked amnesia at the end of the third game]], refuses to hear him out when he tries to explain everything, going so far as to ''flirt'' with his ancestors, and remains abrasive to him for much of the game. All we get are subtle implications that she still has feelings for him up till the end. Seeing their relationship take such a huge backward step can be painful, especially for fans of the [=SlyxCarmelita=] pairing.
** And even at the very end, [[spoiler:just when Carmelita's ''finally'' ready to apologize for being so nasty, all we get is a brief scene of reconciliation... and then Sly gets {{trapped in the past}}, and Carmelita's left with nothing but the photograph of them dating that Sly used to carry around with him.]] [[DownerEnding Never has a sequel been needed as badly as it is now]].
* The WhereAreTheyNowEpilogue of the Cooper Ancestors as you slowly realize that [[spoiler: sooner or later, Clockwerk is going to kill them.]]

!!General

!!Sly Cooper and the Thievius Raccoonus

!!Sly 2: Band of Thieves

** The ending to "Menace in the North, Eh?" also counts. [[spoiler:Jean-Bison sells away all the Clockwerk pieces, thus ruining all the hard work the Gang has done getting them. It is pretty heartbreaking to see them so defeated, and Murray even loses his prized van along the way.]]

!!Sly 3: Honor Among Thieves

!!Sly Cooper: Thieves in Time

* Bentley's reaction to [[spoiler:Penelope being the Black Knight]] certainly serves as one. [[spoiler:He retreats into his shell for the remainder of the episode, until he finally comes through at the last minute to stop her from crushing Sly, earning himself a CrowningMomentOfAwesome as well.]]

** When Bentley finally [[spoiler:confronts Penelope, he makes an attempt to reason with her, showing the gang will let this slide if she realizes [=LeParadox=] is only using her, and will "cut her strings" when he's done. She doesn't listen to ''any'' of his words, and shows she's well beyond the MoralEventHorizon by attacking Bentley in her VillainousBreakdown, showing that if [[DomesticAbuse she can't control him]] [[AmbitionIsEvil for all the money in the world]], [[IfICantHaveYou she'll kill him]] [[IWillPunishYourFriendsForYourFailure and everyone he cares for]]]].

* Bentley's reaction to [[spoiler:Penelope being the Black Knight]] in ''Thieves in Time'' certainly serves as one. [[spoiler:He retreats into his shell for the remainder of the episode, until he finally comes through at the last minute to stop her from crushing Sly, earning himself a CrowningMomentOfAwesome as well.]]
* Sly's backstory in general. His parents were brutally murdered by the Fiendish Five, and he was sent to an orphanage. On the day he was finally going to inherit the Thievius Raccoonus. Which itself was ripped apart and taken by his parents' murderers, depriving him of even a memento (since he likely would have been allowed to keep it as it's a family heirloom).

*** The fact that the events of ''Sly 1'' all take place while Sly and company are about 18. Even for a master thief from a long line of master thieves, to have repeated threats and attempts on your life made by the people that killed your father and destroyed your sole family heirloom before you're even able to legally [[DrowningMySorrows drown your sorrows]] in the country of your birth has to be pretty traumatizing.
* The end of ''Sly 2''. [[spoiler:Bentley goes to grab the Hate Chip that powered Clockwerk, then BAM! He becomes crippled. Murray tries his best to save him, but all Bentley can cry out is, "Pick me up! I can't walk!"]]
** The ending to "Menace in the North, Eh?" also counts. [[spoiler:Jean-Bison sells away all the Clockwerk pieces, thus ruining all the hard work the Gang has done getting them. It is pretty heartbreaking to see them so defeated, and Murray even loses his prized van along the way.]]
* The WhereAreTheyNowEpilogue of the Cooper Ancestors as you slowly realize that [[spoiler: sooner or later, Clockwerk is going to kill them.]]
* The climax of the Arabian level in ''Thieves in Time.'' Ms. Decibel was completely devoted to Le Paradox, and fulfilled the most crucial role in his master plan. But not only did he callously toss her aside when she was beaten by Sly, he cruelly pointed out that ''he never loved her to begin with.'' Villain or not, you have to feel at least ''some'' sympathy for poor, besotted Mz. Decibel.
* When Bentley walks into General Tsao's Palace, you hear him refuse to let his betrothed, [[spoiler: who is the Panda King's daughter, Jing]], be released from prison just to talk to [[spoiler: her father]]. Just hearing her crying about his cruel treatment is enough to put a tear to your eye.
* If you've followed the progress of Sly and Carmelita's complicated relationship in the first three games, the events of ''Thieves in Time'' are particularly painful to watch: Carmelita, angry at Sly [[spoiler: because he faked amnesia at the end of the third game]], refuses to hear him out when he tries to explain everything, going so far as to ''flirt'' with his ancestors, and remains abrasive to him for much of the game. All we get are subtle implications that she still has feelings for him up till the end. Seeing their relationship take such a huge backward step can be painful, especially for fans of the [=SlyxCarmelita=] pairing.
** And even at the very end, [[spoiler:just when Carmelita's ''finally'' ready to apologize for being so nasty, all we get is a brief scene of reconciliation... and then Sly gets {{trapped in the past}}, and Carmelita's left with nothing but the photograph of them dating that Sly used to carry around with him.]] [[DownerEnding Never has a sequel been needed as badly as it is now]].
* Sly's ancestor Rioichi earned the loyalty of a shark he caught while fishing after he spared it. The shark served faithfully as his mount in war for years. After growing to old to fight and seeing that Rioichi wanted to open a sushi restaurant he asked that Rioichi kill and turn him into sushi so his master could open his restaurant. Rioichi agreed, crying as he turned his friend into his restaurant's first meal.
* The opening cutscene of "Honor Among Thieves" chapter of Sly 3. Sly, [[spoiler:who believes he is going to die by some Dr. M's freaky mutant, mourns the botched Cooper Vault job and the fact he never got to see what's in the vault, thinks about his legacy and finally laments how he never took a chance with Carmelita and thinks that he would want to put their "professional differences" behind if he ever meets her again. Even though things turned out well for him in the end, those were his thoughts when he was certain he was going to die.]]

** Jean Bison tried to strike it rich during the Gold Rush of 1852, but wound up [[HumanPopsicle flash-frozen]] in an avalanche, waking up 150 years later. All he wants is to tame the wilderness, as men like him did back then, but the problem is his way of thinking is highly outdated.

*** What's even more tragic is that this is all too realistic. Many real-life criminals have had terrible childhoods themselves.