Cry for the Devil moments in Western Animation.
- The Ice King from Adventure Time at first just seems an ineffectual, lonely, and mildly creepy princess kidnapper. Then we learn his tragic backstory and find out he Was Once a Man and has been slowly driven to madness by an Artifact of Doom, and his fiance left him, and Finn and Jake feel bad for him.
- Amphibia: After turning out to be Evil All Along, King Andrias seems for the first half of Season 3 like a fun but irredeemably cruel and evil Chessmaster whose defeat when it comes will be extremely satisfying. But as the details of his background, his relationship with the Core and his true feelings about Marcy and the planned invasion are fleshed out, he becomes an increasingly tragic character — despite the terrible things he's done, when his downfall actually does come amid a Heel Realization in "All In", it's almost impossible to derive any joy from it.
- Arcane: Despite his horrific actions, it's hard not to feel sympathy for Silco during his trauma flashbacks in episode 3. Watching him desperately fend off a brutal murder attempt from the much stronger Vander, the man he trusted like a brother, is gut-wrenching. Its even more gut-wrenching when he dies, as he says he's willing to throw away his dream for a nation of Zaun just so that Jinx doesn't pay for her crimes, stating his undying love for his adopted daughter before passing away.
- Avatar: The Last Airbender:
- Azula. While she spends most of the series as a standard Magnificent Bastard, her spectacular Villainous Breakdown in the finale drives home that she's just as much Ozai's victim as Zuko is, and even when Zuko and Katara defeat her, they can't feel happy about it. The sheer speed with which her life falls apart has left both the creators and the fandom feeling sorry for her.
- A little bit earlier, Katara discovers an old drawing of a smiling, happy, innocent-looking baby. Zuko then points out that it was a drawing of Fire Lord Ozai himself, which does more to put a face and a history on him than three seasons of characterization previously, as well as remind everyone that Ozai is human too.
- Early, early in Season 1, we were getting this for Zuko — his back-story certainly seemed to explain many of his evil tendencies. But then he went through a long character arc, eventually ending in a Heel–Face Turn, so there was no devil to cry for.
- The Legend of Korra has this for the Big Bad Amon. Turns out he was the eldest son of Yakone, a merciless mob boss from Republic City who used his bloodbending to control people. When Aang took Yakone's bending away, Yakone sought revenge by teaching his two sons bloodbending. There was indeed a time when Amon was just a carefree kid, before the training, which turned him into a self-loathing revolutionary and brutal Knight Templar.
- Batman: The Animated Series:
- Done brilliantly in "Heart of Ice" which focuses on Mr. Freeze and turns him into a Woobie, Destroyer of Worlds. Mr. Freeze is almost completely unemotional, coldhearted and willing to kill anyone who stops him from getting revenge. But his backstory shows that he was trying to save his wife Nora when a heartless exec (who's lauded as a philanthropist) destroyed the lab for wasting money, permanently altering Freeze and nearly killing his wife. The show treats him with an enormous amount of sympathy (his famous "Never again" monologue), Batman is clearly on his side on an emotional level even while trying to stop him, and the target of his vendetta, while not dying, gets his long overdue justice. The episode is always rated as being one of if not the best episodes of the series and benchmark for animated television — there's a reason it won an Emmy.
- Baby-Doll is another example, a woman who has a deformity where she would never grow physically beyond a child, and goes to desperate lengths to try and bring some of the time she was happy back.Baby Doll: (looking at a reflection of herself fully-grown) Look! That's me in there. The real me! There I am! ...But it's not really real, is it? Just made up and pretend, like my family, and my life, and everything else. Why couldn't you just let me make-believe! (shoots at Batman's reflections before facing her adult-form mirror... and firing) I didn't mean to...
- "His Silicon Soul" introduces the Duplicant Batman, an Iron Woobie who you can't help but feel sorry for after his Tomato in the Mirror moment. Especially when he thinks he's killed Bruce. Realizing what Hardac built him to do will kill more innocent people, he sacrifices himself to foil it. Bruce wonders if this meant the duplicate had a soul of his own.Bruce: It seems it was more than wires and microchips after all. Could it be it had a soul, Alfred? A soul of silicon, but a soul nonetheless?
- Killer Croc gets his moment in "Sideshow". After escaping from Batman, he stumbles upon a community of circus freaks who escaped from their cruel masters and have been living in secret away from society. They assume he is like them and welcome him with open arms, telling him he is safe and free to be himself. Croc actually seems to be enjoying himself there, until he learns they have a huge stash of money they keep around for emergencies, and he just can't resist trying to make off with it. As he's being arrested, they ask him why he would betray them after they showed him nothing but kindness, and he sounds genuinely remorseful in his reply.Croc: You said you could be yourself out here, remember? I guess that's what I was doing. Being myself.
- About the only villains in this series that don't elicit sympathy are a Dr. Moreau expy (though his creation did), the Sewer King, Firefly, and the Joker. To be fair, Joker might have a sympathetic backstory. If he ever told anybody his real one.
- Ed, Edd n Eddy has good ol' Eddy whose greed and arrogance is hard to surpass. More often than not, the viewer is shown he's a selfish jerk. In the last five minutes of the movie, we see that Eddy is the way he is as a result of his older brother's abuse. Eddy was just trying to fit in and be cool, but he never figured out how to do it right because his brother constantly mistreated him while mentoring him to be cruel and self-serving.
- Gargoyles has a tendency to do this with a number of its villains. In particular, the flashbacks in the multi-parter City of Stone are basically this for Demona and Macbeth writ large (also their mutual Start of Darkness), but even Xanatos can elicit this reaction when trying desperately to save his newborn son from Oberon.
- My Little Pony: Friendship Is Magic: By the end, you really have to feel sorry for Cozy Glow. First, she's implied to be an orphan. Second, she is sentenced to spend eternity in Tartarus rather than being sent to a normal prison despite several adult characters having done as bad as her and been given full pardons for their crimes simply because they showed remorse, as if simple remorse should mean the difference between a full pardon and life imprisonment, instead of anything else in between. Finally, she is forcibly broken out of Tartarus only to be railroaded into an even harsher punishment by Discord, who convinces the princesses to turn her into stone, while he gets off with nothing more than a scolding, despite the fact that he enabled all her new actions, none of which were really any worse than her previous ones, and she would have still been in Tartarus if not for him. Making this worse is that she actually showed signs of reforming in the episode "Frenemies" before Chrysalis talked her out of it, and in the end, she and Tirek both stand down after they are defeated, and they may very well have been given one final chance to turn themselves around had Chrysalis not kept running her mouth.
- Primal (2019): The infected Argentinosaurus from "Plague of Madness". The poor thing wasn't even malicious to begin with; it was just a peaceful herbivore who got bitten by an infected dinosaur and turned into an Ax-Crazy monster as a result. Unlike the viewer, Spear doesn't get to see it living peacefully among its herd, but still comes to the same conclusion nonetheless and looks genuinely saddened by the monster's death. The somber music that plays as it the lava flames char it out of its misery only makes it more pitiable.
- In-story example in She-Ra: Princess of Power: Evil Overlord Hordak has been poisoned, and the magic poison will kill him within a certain time period if he cannot find anyone willing to cry for him. Since She-Ra doesn't want anyone to die, even Hordak, she helps him by taking him to see almost everyone he's ever known, learning about his history along the way. With time almost up, it turns out that there is nobody at all who won't be glad to see Hordak dead. She-Ra herself cries over the realization of just how thoroughly Hordak has wasted his life.
- An episode of Storm Hawks has Master Cyclonis attack the titular characters to steal a crystal from them which she needs to repair a broken crystal of her own. She actually pulls it off, returns to her Supervillain Lair and repairs the crystal... which projects a holographic image of her as a young child with her grandmother. Cyclonis almost starts crying.
- Wakfu: This trope is practically a standard for every Big Bad in the series.
- Every slight hint of Nox's history. The first glimpse of his history is a dream of a loving wife and children on a beautiful summer day. Given that he's now a cackling maniacal villain looking to turn back time or break the very fabric of reality in the attempt because nothing else matters to him anymore, it's safe to say things didn't go well for his family. The bonus episode "Noximilien" is entirely made of this and Start of Darkness. In the end, he finally achieves his goal and rewinds time, hoping to save his family and undo all the horrible things he's done over the last two hundred years... and it only goes back twenty minutes. All the atrocities he's forced himself to commit, all the struggle he's caused, all the pain everyone's suffered, rendered completely pointless. He's so broken by this he goes to the graves of his family and kills himself. And because the world never knew about his motives, he'll go down in history as a Generic Doomsday Villain. Woobie, Destroyer of Worlds doesn't even begin to cover it.
- Although he's widely considered far less sympathetic than Nox, Qilby still does this. He's a remorseless, treacherous, planet-destroying Straw Nihilist who cares entirely about his own benefit and refuses to show regret for his many crimes, but he's become the way he is due to thousands (possibly even billions) of years of being cursed with true immortality and forced to retain his memory of it all, and knowing that it will never end, and furthermore having no-one but his dragon twin Shinonome who understood his burden. It doesn't help that it's implied that the rest of his siblings did in fact neglect Qilby and undervalue the vast intellect his immortality afforded him, regulating him to being a glorified librarian. Qilby arouse pity when his own sister turns against him in order to stop his madness and he's left crippled, crawling and desperately begging for her help. Him being locked again in the Blank White Void where he spent thousands of years in catatonia, all alone and suffering the fate he feared most, is very much an Alas, Poor Villain moment that has a strong impression on the audience.
