History AlasPoorVillain / WebOriginal

** One of the two major antagonists of Volume 9 gets a degree of pathos at the end. [[spoiler:After the [[EvilAllAlong Curious Cat]] is beaten down, their last exchange with Ruby highlights their ruined mental state, heavily implying they know on some level that they're as broken as they claim humans are but they can't do anything about it. Moments later, the Cat is devoured by Neo's Jabberwalker clones while screaming in terror, a swift but brutal affair which Team RWBY react to with horror. Post-mortem, the Blacksmith expresses sorrow for the Cat's turn for the worse and the fact they couldn't be fixed by the Tree, and the flashback of the Cat's beginnings which highlights [[UsedToBeASweetKid their original character]] hammers home the tragedy of their "unfortunate change" due to circumstances that were beyond their ability to change]].

%%* In the tradition of its [[VideoGame/MetalGear source material]], ''FanFic/{{Stray}}'' does this for one of its villains - the TykeBomb Patriot agent Esau.

** [[Characters/RWBYAdamTaurus Adam Taurus]] is a {{Fantastic Terrorist|s}} who wants to [[MasterRace enslave humanity to the Faunus]]. However, he becomes [[PsychoExBoyfriend increasingly obsessed]] with destroying Blake [[DomesticAbuse for leaving him]], permanently maiming her team-mate Yang and trying to assassinate her parents. The final confrontation between him, Blake and Yang stops being a CatharsisFactor when he reveals that his mask was hiding a Schnee Dust Company brand across his left eye. Although it doesn't excuse his abuse and terrorism, it does reveal that humans had subjected him to terrible abuse, setting him on the road to becoming a monster. The creators confirmed they did want the audience to feel some pathos for him at the end.
** [[Characters/RWBYJamesIronwood James Ironwood]] [[JumpingOffTheSlipperySlope descends into villainy]] in his [[WellIntentionedExtremist single-minded drive]] to save Atlas, the Relics and the Winter Maiden from [[BigBad Salem]]; it leaves him broken, isolated and utterly abandoned. He fails to save either Atlas or the Relics, and he is abandoned by the heroes, Winter Maiden, and even Winter, who manage to save thousands of lives without him. Injured and defeated, he watches from the ground as Salem collects the Relics from Cinder and departs without ever acknowledging his existence; even the normally boastful Cinder simply declares "And that's checkmate." before leaving him to his fate on a crashing Atlas.

* In the ''WebAnimation/DeathBattle'' match between [[Characters/MarvelComicsMagneto Magneto]] and [[Manga/{{Akira}} Tetsuo]], [[spoiler:Magneto spends the entirety of the fight simply defending himself and trying to deal with [[PsychopathicManchild an annoying enemy]]. However, after Tetsuo enters his [[OneWingedAngel "Ego Death" form]] and [[PowerIncontinence telepathically begs for help]], Magneto goes through a complete 180 and does everything in his power to end the fight quickly and MercyKill the suffering teen with [[SugarWiki/HeartwarmingMoments Tetsuo's last words being "Thank you."]]]]

** Adam Taurus is a {{Fantastic Terrorist|s}} who wants to [[MasterRace enslave humanity to the Faunus]]. However, he becomes [[PsychoExBoyfriend increasingly obsessed]] with destroying Blake [[DomesticAbuse for leaving him]], permanently maiming her team-mate Yang and trying to assassinate her parents. The final confrontation between him, Blake and Yang stops being a CatharsisFactor when he reveals that his mask was hiding a Schnee Dust Company brand across his left eye. Although it doesn't excuse his abuse and terrorism, it does reveal that humans had subjected him to terrible abuse, setting him on the road to becoming a monster. The creators confirmed they did want the audience to feel some pathos for him at the end.
** Ironwood [[JumpingOffTheSlipperySlope descends into villainy]] in his [[WellIntentionedExtremist single-minded drive]] to save Atlas, the Relics and the Winter Maiden from [[BigBad Salem]]; it leaves him broken, isolated and utterly abandoned. He fails to save either Atlas or the Relics, and he is abandoned by the heroes, Winter Maiden, and even Winter, who manage to save thousands of lives without him. Injured and defeated, he watches from the ground as Salem collects the Relics from Cinder and departs without ever acknowledging his existence; even the normally boastful Cinder simply declares "And that's checkmate." before leaving him to his fate on a crashing Atlas.

* {{Discussed}} in ''WebOriginal/TheDeathOfRussia''. The massacre of Russian [=POWs=] by Chechen forces is at least somewhat considered a tragedy in later years, despite being met with schadenfreude and cheers in the 1990s. In the words of an in-universe history book, "There was only so much 'It's okay to punch Nazis' or 'Reds are better Dead' that one could repeat to themselves before the sight of [[IWantMyMommy teenagers pleading for their mothers]] as their throats are slit would break one's soul".

* Although a lot of the villains in ''Machinima/ArbyNTheChief'' are usually downright [[{{Narm}} over-the-top]] like Craig, or downright [[HateSink hateful]] like Adam, the series's final villain, Eugene Black is certainly an interesting case of this. As evident throughout the show's final season, he's a downright sadist who has no trouble letting his psychopathic or pedophile friends do as they wish to people online, as well as enjoys forcing hundreds of innocent people to replace their Xbox 360s after banning them with a hardware corrupting software over a period of 2 months, [[ForTheEvulz just for laughs]]. On the flipside though, he's also a failing student at his school (despite [[JerkassWoobie also being a bully too]]), [[AbusiveParents is constantly abused by his Drunk (and sometimes neglectful) Father]], and his sister (the only source of happiness in his life) is dying a slow and agonizing death of Leukemia. It's hard whether to feel sorry for him for how crappy his life is, or to hate him for how much of a bastard he is just to repress these feelings. [[spoiler:To add insult to injury, this only get worse for him, and he's DrivenToSuicide by the show's end]].

* In the Season 10 finale of ''Machinima/RedVsBlue'', the defeat of the Director emphasises the tragedy that consumed his life. [[spoiler:Carolina finds him locked in a bunker watching on endless repeat the video of the last time he ever saw his wife alive. He realises he has been futilely chasing a ghost for years and neglected his relationship with his daughter. He asks Carolina for a pistol, makes peace with her and and F.I.L.L.S, and then is heavily implied to commit suicide.]]

** Adam Taurus is a {{Fantastic Terrorist|s}} who wants to overthrow humanity and [[MasterRace enslave them to the Faunus]]. However, he becomes [[PsychoExBoyfriend increasingly obsessed]] with destroying Blake [[DomesticAbuse for leaving him]], permanently maiming her team-mate Yang and trying to assassinate her parents. The final confrontation between him, Blake and Yang stops being a CatharsisFactor when he reveals that his mask was hiding a Schnee Dust Company brand across his left eye. Although it doesn't excuse his abuse and terrorism, it does reveal that humans had subjected him to terrible abuse, setting him on the road to becoming a monster. The creators confirmed they did want the audience to feel some pathos for him at the end.

** Adam Taurus is a FantasticTerrorist who wants to overthrow humanity and [[MasterRace enslave them to the Faunus]]. However, he becomes [[PsychoExBoyfriend increasingly obsessed]] with destroying Blake [[DomesticAbuse for leaving him]], permanently maiming her team-mate Yang and trying to assassinate her parents. The final confrontation between him, Blake and Yang stops being a CatharsisFactor when he reveals that his mask was hiding a Schnee Dust Company brand across his left eye. Although it doesn't excuse his abuse and terrorism, it does reveal that humans had subjected him to terrible abuse, setting him on the road to becoming a monster. The creators confirmed they did want the audience to feel some pathos for him at the end.

** Adam Taurus is a [[FantasticTerrorism terrorist]] who wants to overthrow humanity and [[MasterRace enslave them to the Faunus]]. However, he becomes [[PsychoExBoyfriend increasingly obsessed]] with destroying Blake [[DomesticAbuse for leaving him]], permanently maiming her team-mate Yang and trying to assassinate her parents. The final confrontation between him, Blake and Yang stops being a CatharsisFactor when he reveals that his mask was hiding a Schnee Dust Company brand across his left eye. Although it doesn't excuse his abuse and terrorism, it does reveal that humans had subjected him to terrible abuse, setting him on the road to becoming a monster. The creators confirmed they did want the audience to feel some pathos for him at the end.

* In the eighth volume of ''WebAnimation/{{RWBY}}'', Ironwood [[JumpingOffTheSlipperySlope descends into villainy]] in his [[WellIntentionedExtremist single-minded drive]] to save Atlas, the Relics and the Winter Maiden from [[BigBad Salem]]; it leaves him broken, isolated and utterly abandoned. He fails to save either Atlas or the Relics, and he is abandoned by the heroes, Winter Maiden, and even Winter, who manage to save thousands of lives without him. Injured and defeated, he watches from the ground as Salem collects the Relics from Cinder and departs without ever acknowledging his existence; even the normally boastful Cinder simply declares "And that's checkmate." before leaving him to his fate on a crashing Atlas.

* In the Season 10 finale of ''Machinima/RedVsBlue'', the defeat of the Director emphasises the tragedy that consumed his life. [[spoiler:Carolina finds him locked in a bunker watching on endless repeat the video of the last time he ever saw his wife alive. He realises he has been futilely chasing a ghost for years and neglected his relationship with his daughter. He asks Carolina for a pistol, makes peace with her and and F.I.L.L.S, and then is heavily implied to commit suicide.]]
* In the eighth volume of ''WebAnimation/{{RWBY}}'', Ironwood [[JumpingOffTheSlipperySlope descends into villainy]] in his [[WellIntentionedExtremist single-minded drive]] to save Atlas, the Relics and the Winter Maiden from [[BigBad Salem]]; it leaves him broken, isolated and utterly abandoned. He fails to save either Atlas or the Relics, and he is abandoned by the heroes, Winter Maiden, and even Winter, who manage to save thousands of lives without him. Injured and defeated, he watches from the ground as Salem collects the Relics from Cinder and departs without ever acknowledging his existence; even the normally boastful Cinder simply declares "And that's checkmate." before leaving him to his fate on a crashing Atlas.

* Although a lot of the villains in ''Machinima/ArbyNTheChief'' are usually downright [[{{Narm}} over-the-top]] like Craig, or downright [[HateSink hateful]] like Adam, the series's final villain, Eugene Black is certainly an interesting case of this. As evident throughout the show's final season, he's a downright sadist who has no trouble letting his psychopathic or pedophile friends do as they wish to people online, as well as enjoys forcing hundreds of innocent people to replace their Xbox 360s after banning them with a hardware corrupting software over a period of 2 months, [[ForTheEvulz just for laughs]]. On the flipside though, he's also a failing student at his school (despite [[JerkassWoobie also being a bully too]]), [[AbusiveParents is constantly abused by his Drunk (and sometimes neglectful) Father]], and his sister (the only source of happiness in his life) is dying a slow and agonizing death of Leukemia. It's hard whether to feel sorry for him for how crappy his life is, or to hate him for how much of a bastard he is just to repress these feelings. [[spoiler:To add insult to injury, this only get worse for him, and he's DrivenToSuicide by the show's end]].
* ''WebVideo/AskThatGuyWithTheGlasses'' goes out with a strange mix of this and DeathAsComedy. In the GrandFinale, someone asks him "do you have a question?". He gets so excited that someone finally thought about what ''he'' wanted that he literally explodes. {{Lampshade|Hanging}}d by Chester A. Bum, who is sad when he first finds out about That Guy's death, but then realizes that he was a terrible person and it's probably a good thing he's gone.
* ''WebAnimation/LlamasWithHats'': It's oddly heartbreaking when Carl in the final episode gets DrivenToSuicide by [[EvenEvilHasLovedOnes the realization that he's killed his former best (and probably only) friend]] along with everyone else on Earth.
* ''WebVideo/CriticalRole'' has one with Delilah Briarwood. She and her husband Sylas are, by all accounts, a [[UnholyMatrimony loving couple]] who care for one another very, very deeply. They are also truly terrible people, and are the ones responsible for the massacre of protagonist Percy's family and household and the trauma he endured as a result, as well as unknown other evils. But even after the horrible things they did, critters and players felt bad [[spoiler:for Delilah, due to her absolutely heartbroken reaction when she saw Sylas killed right before her eyes]].
* ''WebVideo/MarbleHornets'': The two main antagonists of the series, [[spoiler:Alex and Brian, both die with some degree of sympathy. Alex practically begs Tim]] to finish what he started, implying that while he may have gone [[AxCrazy Ax-Crazy]], he nonetheless believed that what he was doing was right. [[spoiler:Brian]], on the other hand, [[spoiler:is revealed to be the Hooded Man shortly after his own demise. Seeing the sharp contrast between his personalities before and after encountering the Operator]] makes the viewer sympathize with him as well.
* ''Podcast/TheAdventureZoneBalance'' has a couple examples:
** At the end of ''The Suffering Game'', [[spoiler: Lydia dies of despair when Edward is killed; in her final moments, she drops her illusory form in favor of her true black robes, and, at a loss for words, simply screams.]]
** [[spoiler: John might be the source and avatar of the Hunger, but watching him get subsumed by it is more than a little tragic. His actual death, watching the sunset with Merle before fading away, only makes him more sympathetic.]]

* ''Machinima/RedVsBlue'': In the Season 10 finale, the defeat of the Director emphasises the tragedy that consumed his life. [[spoiler:Carolina finds him locked in a bunker watching on endless repeat the video of the last time he ever saw his wife alive. He realises he has been futilely chasing a ghost for years and neglected his relationship with his daughter. He asks Carolina for a pistol, makes peace with her and and F.I.L.L.S, and then is heavily implied to commit suicide.]]
* In ''WebAnimation/{{RWBY}}'': Ironwood [[JumpingOffTheSlipperySlope descends into villainy]] in his [[WellIntentionedExtremist single-minded drive]] to save Atlas, the Relics and the Winter Maiden from [[BigBad Salem]]; it leaves him broken, isolated and utterly abandoned. He fails to save either Atlas or the Relics, and he is abandoned by the heroes, Winter Maiden, and even Winter, who manage to save thousands of lives without him. Injured and defeated, he watches from the ground as Salem collects the Relics from Cinder and departs without ever acknowledging his existence; even the normally boastful Cinder simply declares "And that's checkmate." before leaving him to his fate on a crashing Atlas.

* ''WebAnimation/{{RWBY}}'': One of the heroes [[JumpingOffTheSlipperySlope descends into villainy]] in their [[WellIntentionedExtremist single-minded drive]] to save the city, Relics and Maiden they're responsible for protecting from [[BigBad Salem]]; it leaves them broken, isolated and utterly abandoned. [[spoiler:Ironwood fails to save either Atlas or the Relics, and he is abandoned by the heroes, Winter Maiden, and even Winter, who manage to save thousands of lives without him. Injured and defeated, he watches from the ground as Salem collects the Relics from Cinder and departs without ever [[NotWorthKilling acknowledging his existence]]; even the normally boastful Cinder simply declares [[BreakTheBadass "And that's checkmate."]] before leaving him [[DyingAlone to his fate]] on a crashing Atlas.]]

* ''WebAnimation/{{RWBY}}'': Ironwood [[JumpingOffTheSlipperySlope descends into villainy]] in his [[WellIntentionedExtremist single-minded drive]] to save Atlas, the Relics and the Winter Maiden from [[BigBad Salem]]; it leaves him broken, isolated and utterly abandoned. [[spoiler:He fails to save either Atlas or the Relics, and he is abandoned by the heroes, Winter Maiden, and even Winter, who manage to save thousands of lives without him. Injured and defeated, he watches from the ground as Salem collects the Relics from Cinder and departs without ever acknowledging his existence; even the normally boastful Cinder simply declares "And that's checkmate." before leaving him to his fate on a crashing Atlas.]]

* CT in ''Machinima/RedVsBlue'' (no, not the one from Season 7, the real Freelancer who the Rebel Leader took the identity of) was never really a villain in the first place, but instead ended up becoming a HeroAntagonist to try and take down the Director. Her reward for trying to do the right thing? A throwing axe to the chest which mortally wounds her, causing her to die in her lover's arms.
** The Director also got a moment like this in the finale of Season 10, when he realised he should have spent more time looking after his daughter Carolina, realises that he has been chasing at ghosts futilely for several years, asks Carolina for a pistol, makes peace with her and F.I.L.L.S and then is implied to commit suicide.

* In the ''Roleplay/GlobalGuardiansPBEMUniverse'', the villain Hardcase was generally thought of as a brutish, selfish thug who liked to beat up women for fun, drank too much, and was generally a sleaze. And on September 11, 2001, he gave his life by using his superhuman strength to save people from the collapsing North Tower of the World Trade Center. The heroes not only campaigned to get him a posthumous presidential pardon, they sprang for a funeral the likes of which are normally reserved for deceased presidents and popes.

* Parodied in Part 3 of the WebVideo/BenMcyellow series. Despite being a [[SlasherSmile gleefully psychotic]] BloodKnight with absolutely no sympathetic qualities, when fatally wounded, [[TheDragon Lord]] [[TheBrute Sword]] slowly falls to his knees with great dignity while mournful music plays. Then when his body finally hits the ground, [[MoodWhiplash he instantly vanishes with a fart sound effect.]]

* Parodied in Part 3 of the WebVideo/BenMcYellow series. Despite being a [[SlasherSmile gleefully psychotic]] BloodKnight with absolutely no sympathetic qualities, when fatally wounded, [[TheDragon Lord]] [[TheBrute Sword]] slowly falls to his knees with great dignity while mournful music plays. Then when his body finally hits the ground, [[MoodWhiplash he instantly vanishes with a fart sound effect.]]