Despair Gambit

What's a villain to do when the hero is invincible, or at least too strong to attack head on? Whether because of tactics, defense, The Power of Love, will, or because he won the Superpower Lottery, the conventional tactics just aren't going to do the trick. By contrast, perhaps the villain himself is so weak that physical attack is impractical, or stands to gain if his enemies are not merely killed but admit utter defeat. In such a case, a good alternative strategy is often to attack the hero's resolve, and make him give up the fight.

Blow up his hometown. Kill his loved ones. Spout cutting Hannibal Lectures and Nietzsche Wannabe speeches at every opportunity. Steal his belongings. The ultimate goal is to drive the goodie past the Despair Event Horizon, making him more an enemy to himself than to the villain.

As with other such plots, it tends to backfire. Hurting the hero on this level makes it personal, incurring the risk of focusing the hero's attention squarely against the villain, or even triggering an Unstoppable Rage. There's also the possibility of riling a previously neutral party. Because the story tends to be on the hero's side, this gambit is more likely to fail in the long run, though it may succeed in evaporating his hope at a critical point.

This is a common tactic of the invading army, the intent being to weaken the defense by subduing its morale. This is also the basic idea behind terrorism.

See also Villain Ball, Driven to Suicide, Despair Event Horizon and Despair Speech.

Anime and Manga

 * This is the Anti-Spiral modus operandi in Tengen Toppa Gurren Lagann, arranging Manchurian Agents, Colony Drops and Hope Spots because the Power of the Spiral can't be defeated through main force. Although this is effective on some characters, it ultimately backfires, leading Team Gurren to the Anti-Spirals' home dimension and giving them a plethora of Lagann-type mechs with which to take them down.
 * This is Knives' instruction to his minions in Trigun, in the hopes that it will make Vash give up his stewardship of humans and join the other side. In the anime,.
 * In Gun X Sword, Woo not only defeats Van in battle but also forces Van to recognize his own terror and confront the possibility of dying. It nearly works: Van is so shaken by his new fear of death that he is prepared to give up his revenge quest and run away. Fortunately, his sidekick calls him on his cowardice and challenges him to man up. The Power of Love does the rest.
 * The "Revenge Arc" of Rurouni Kenshin deals with Enishi's attempt to reduce Kenshin to a pathetic homeless wreck by destroying everything Kenshin holds dear, in revenge for Kenshin's (accidental) killing of Enishi's sister.
 * In .hack//Sign the plot of the main villain involves a whole lot of this.

Comics

 * Lex Luthor defeats Superman in Superman Red Son in this way: after every attempt to take out Superman by brute force fails, he attacks Superman's psyche instead with an Armor-Piercing Question.
 * The Joker has done this several times, such as in The Killing Joke and the film partially based on it, The Dark Knight. He does it either because that's the way he is or because he secretly, desperately wants to prove that everyone else is really as hopeless as he is.
 * Ozymandias convinces Doctor Manhattan that he's giving his acquaintances cancer in Watchmen, basically for this purpose.
 * Following the death of his brother, the villain Kraven, Spider-Man villain Chameleon became increasingly crazy and devoted himself to putting Spider-Man through one of these, and along the way, he confirmed/learned Spider-Man's identity. This included convincing Peter he was in a Cuckoos Nest scenario and was actually an unhinged and depressed writer, as well as trying to attack Peter's family and friends.

Film

 * In The Patriot the British general burns a church with it's town inhabitants still inside, including the newly married wife of one of the main characters. When the patriot army descends upon the village it prompts one of the soldiers who just lost his family to shoot himself in the head.

Literature

 * In Harry Potter, the Death Eaters use this at least as a supplemental strategy, striking randomly at civilian targets to foster fear among the populace. (In theory, they're targeting those who they deem impure, but by their standards that's pretty much everyone)
 * Once Sauron loses his body, this becomes one of his main tactics. In addition to the more overt Mind Rape of the Nazgul and the intimidation tactics used at Pelennor, he twists the Palantiri so that his enemies gradually lose all hope of vanquishing him. This prompts Saruman to commit a Face Heel Turn and start collaborating with him, and Denethor to send his own son off to die and commit suicide in the midst of the decisive battle. In the film, Denethor's condition is even worse, such that he refuses even to send for help and even orders his soldiers to abandon their posts.
 * It eventually becomes clear that this is one of the Dark One's main goals in The Wheel of Time: hurt the Dragon personally until he turns or takes himself out. In The Gathering Storm,.
 * In the novel Superman: Miracle Monday, The Devil's agent on Earth tries this on Superman (by trying to trick him into killing an innocent person) hoping to break his spirit (and in turn, the inspiration he provides humanity.) It fails because Superman just won't do it.
 * Frankly, the elaborate revenge undertaken by The Count of Monte Cristo consists of his putting his enemies through one of these.
 * In The Dresden Files,

Tabletop Games

 * Warhammer and Warhammer 40000 both feature Nurgle, the Chaos God of Pestilence and Despair. When mortals watch their loved ones wither from disease, or despair as their bodies bloat and decay from a hideous plague, they turn to Nurgle to escape the terror of their imminent death. Rather than cure them, Nurgle's blessings allow his followers to survive his disgusting attentions free of pain or fear, trading their immortal souls to preserve their disfigured and corrupted flesh. The process leaves Nurgle's followers with a morbid sense of good humor and eager to lead others into "Grandfather Nurgle's" scabrous embrace.

Video Games

 * In Knights of the Old Republic 2, the protagonist actually uses this to defeat Darth Sion. His connection to the Force basically makes him invincible, so in order to kill him for good, the player has to convince him to give up that connection willingly and die.

Web Comics

 * A pair of pages of Super Stupor lampshades the danger of this: The villain apparently didn't anticipate that "proving" to a superhero that killing is A-OK by killing his girlfriend is only a good idea when you're ready to sacrifice your own life in the name of your political statement.