This is when the villain has developed a devious plot that is prepared for anything and the hero might do — except for one glaring flaw. For some reason, the villain has not considered the possibility of a Heroic Sacrifice. After all, you'd never catch him throwing his life away to save a bunch of lazy, ungrateful civilians who don't care about anybody except themselves. Heck, even saving your True Companions comes after saving your own life. Only an idiot would throw his life away like that—and only because he didn't realize how much more profitable saving it would be. Sometimes that PR would be bad, but you only have to get him to where he can act secretly to get it out of him.
Too bad for the villain that Machiavelli Was Wrong, for they cannot understand the concept of goodness or generosity because there is no guaranteed return on that investment. Why do they have so much trouble understanding good behavior?
Our Hero goes and makes the Heroic Sacrifice anyway, thereby ruining the villain's plan with a Didn't See That Coming that a more cunning villain really should have seen coming. This is one of the ways those with Honor Before Reason can continue to defeat the Big Bad. This is a major problem for villains who really believe they are Not So Different and think heroes could have used their powers for Evil, as opposed to villains who are just screwing with the Hero's head.
Occasionally, greater justification is provided by having a hero who the villain knows is a Jerkass and the Anti-Hero decides to redeem himself at the critical moment, or the villain will meet a hero who decides to Turn the Other Cheek instead of fighting back.
The inability to comprehend good altruistic behavior (especially when it results in punishment) is a common trait in cynics, Straw Nihilists, Corrupt Corporate Executives, Social Darwinists, Knight Templars, and sociopaths (who really are incapable of feeling things that have no selfish incentive, such as compassion). This is Truth in Television in many cases.
An alternative version involves the Hero giving in to the villain's manipulative demands, agreeing that, yes, We Can Rule Together (usually to the horror of his sidekicks, Love Interest, and True Companions) as a ruse to defeat the villain. The villain falls for it because it's what he'd have done if the situations were reversed.
Greedy villains may content themselves with bribing the hero. After all, justice and revenge aren't shiny and don't get a good exchange rate. Yet The Hero goes and turns down the Briefcase Full of Money or a share in the proceeds of a robbery. Villains solely motivated by greed, power or ambition can never find true happiness, indeed. The Green-Eyed Monster often assumes that The Hero is equally preoccupied with whatever inspired their envy.
The Knight Templar Fundamentalist won't realize that other people differ about the relative values of what they support versus what they're willing to sacrifice for its sake, wrongly assume they're the "good guy" (when they're obviously not), and don't understand why Pay Evil unto Evil in the name of "law, order and justice" would be morally wrong.
Innocent Bystanders and Mooks leave the villain even more certain. A Doomed Moral Victor's inspiration or a Heroic Bystander will flabbergast these villains, as will a Mook's Heel–Face Turn that is inspired by the hero's example, or a Mook who proves that Even Evil Has Standards. Indeed, he may help the Mook along by threatening their loved ones.
Never underestimate The Power of Love and The Power of Friendship. True friendship requires acts of kindness and thoughtfulness, which is selfless and understanding. Being self-centered makes it nearly impossible for a villain to understand or embrace the necessary demands of friendship. They tend to believe in self-preservation and the interests of the individual above all things, act in their own self-interest, and assume “heroes” enslave people to an arbitrary system of rules and dogma. Pride is by nature competitive, pitting the arrogant villain against anyone and everyone — they simply can’t understand The Power of Friendship, which is a form of love, placing it beyond the realm of their understanding. Plus, while the villain may be surrounded by countless lackeys and toadies whom he keeps them in line via threats or outright violence, the hero has True Companions, love interests and friends who are willing to help them even in dire situations and enable them to defeat the baddies.
Similarly, the The Leader who's a Father to His Men would command more respect from allies than a Bad Boss who keeps his Mooks in line via fear and considers them expendable. Truly, Machiavelli Was Wrong indeed, and the Big Bad is in for a surprise if his henchmen voluntarily defect to the other side after realizing the Big Good treats them better than their boss. Plus, the needs of many trumps self-preservation, as the villain always fails to recognize that ruling by fear won't get them allies.
The same thing goes with The Power of Love — villains would regard it as a bizarre and alien concept, and are completely blindsided when the hero Took a Third Option to not only save his love interest and allies, but also the city from the villain's clutches. Cue an epic Kirk Summation or Shut Up, Hannibal! when the villains go on a Motive Rant, where the hero not only calls the villain out for his crimes, and for his inability to understand compassion or what motivates the good. At times, when both the villain and hero are in mortal danger, the villain may be utterly bewildered as to why anyone would try to save their enemy.
A favored ethical position of Socratic and Platonic philosophers, who hold that goodness is wisdom and understanding and that no-one does evil simply For the Evulz. In other words, evil does not so much fail to understand good as it can only be evil at all because it fails to understand good.
The God of Evil, Satan, or other beings that are Made of Evil are normally shown as being incapable of understanding things like compassion or goodness. In this case, pure evil cannot understand something that their nature renders them unable to experience themselves. This is Older Than Feudalism: The Bible often depicts the Devil in this fashion, where he's unable to appeal to anything other than selfish desires when manipulating humans. This is often the reason a Deal with the Devil fails; the deal maker's inability to understand good leaves a loophole that someone who can is able to take advantage of, or simply offer something that doesn't truly matter to the target.
Contrast It's All About Me, when the villain expects the hero to behave not selfishly, but generously toward him. When the trope is Evil Cannot Comprehend Good, the villain can't understand why the hero saved him from falling; in It's All About Me, the villain can't understand why the hero insists on arresting him after. It can get a little fuzzy when the character decides to be generous: did he murder his son's romantic rival because he didn't realize his son would hate it — this trope — or because he was so caught up in the notion of his own generosity that he didn't care what his son thought—It's All About Me?
Also contrast Virtue Is Weakness, where the villain actually does comprehend what goodness entails, but sees it only as a weakness in others to be exploited. Although it is still possible for the villain to share both of these tropes, such as if the villain doesn't understand why the others doesn't share the same views as they do.
Supertrope of Beware the Honest Ones and subtrope of Wrong Assumption. Contrast Good Is Old-Fashioned, Silly Rabbit, Idealism Is for Kids!, and the Inverted Trope of Good Cannot Comprehend Evil. Compare Blue and Orange Morality. Often involves Psychological Projection. When someone evil is capable of understanding or admiring good, it may lead to Sympathy for the Hero. If this trope is at work, it's because the villain thinks he is the good guy and is baffled at the heroes wanting to stop him, it's because he's Obliviously Evil. Curious Qualms of Conscience could be similar to a milder form—characters who doesn't understand the good and the conscience within themselves.
As an aside, there is a definitive, IRL version of this: sociopaths are afflicted with a mental disorder, Antisocial Personality Disorder. One of their main (and deadly) traits is that they, quite literally, cannot grasp the concept of goodness due to their Lack of Empathy. They lie constantly and incessantly, manipulate others over the smallest thing, and sometimes do it for no gain at all other than to gratify themselves, and will kill with no compunction other than to waste some time... and they think others are Not So Different. They cannot even begin to imagine why anyone would care about or show mercy to anyone else, cannot empathize in any way, nor can they form emotional connections deeper than lust or raw desire. At heart, they're mentally unable to even imagine goodness, kindness, friendship or love. They know the concepts do exist, but to them, it's just an urban legend that others spout nonsensically. So yes, they view good as a fad or scoff at it.
Ha ha ha! Those pesky Tropers will keep all of the examples on one page, so it's easier to control - just like I would do! Wanna bet?
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Wait, what do you mean you spread them across multiple subpages? This Cannot Be!! Noooo!