Villains aren't usually sympathetic. They're the bad guys, always working to maim, conquer, and control people's souls. However, supervillains are fundamental to the superhero genre's fabric. If they were just death rays and maniacal laughter they'd get boring fast. That's why creators have to explore the villains' vulnerable sides. A lot of the time this takes the form of a tragic backstory, but sometimes villains are victims themselves.
The victims of their own plans, victims of other villains, sometimes even the victims of overzealous Champions of Good and Right. These moments stick with us. They remind us that, even if these bad guys are sick and wrong, they're still human. Or aliens. Regardless, we're a little bit like they are. Our fears and losses are the same as theirs.
10 Not a Riddle Anymore
The Riddler wasn't presented as a mentally ill character for a long time. Created in the 40s, it wasn't until the 1990s that he received - and rejected - his OCD diagnosis. A spin-off of Batman: The Animated Series, Gotham Adventures #11 tells a fairly standard Riddler story.
He goes out on a crime spree, leaving a clue at every scene, and even almost defeats the Dark Knight and gets away. At the story's climax, though, he stops fighting and turns himself in to ask for help. Nygma didn't know he'd been leaving clues, and realized rumors of his insanity might not be exaggerated.
9 The Monarch Loses His Trust Fund
Named after the butterfly, Venture Brother's antagonist The Monarch isn't exactly a top-tier supervillain. He's cunning and occasionally deadly, but impossibly petty and self-absorbed. The one thing the Ventures' nemesis has had from the beginning, though, was enough money to fuel his unhealthy obsession.
In Season 7 The Monarch got some bad news. Buying flying cocoons and Buttergliders had blown through his inherited fortune and he was forced to go live in his parents' old place. It's a dilapidated mansion, which is appropriate for a villain, but the neighborhood's so bad he can't even get a pizza delivered. Ouch!
8 Victor Fries Loses Nora
When Mister Freeze appeared in 1959, he was just another Batman rogue. He had an ice theme and some cool weapons, but he was just another super baddie trying to steal diamonds. Batman: The Animated Series saw something was missing and fixed him with the story "Heart of Ice."
Enter Dr. Victor Fries, secretly experimenting with cryogenics on his employer's dime, trying desperately to save his wife's life. Nora Fries was terminal, but he hoped freezing her body could sustain her. GothCorp's CEO personally pulled the plug on the experiment, resulting in an explosion that both lost Nora's body and transformed Fries into Freeze. Even when he returns with murder in mind, it's impossible to not feel for the man who's lost everything, and can't feel sunlight on his skin ever again.
7 Doctor Horrible Is Real
In 2008, while Hollywood writers were busy striking, an elite group of Hollywood nerds was making movie magic. Doctor Horrible's Sing-A-Long Blog introduced several great characters, with none outdoing Neil Patrick Harris' portrayal of Horrible himself.
It's a comedy but ends on the darkest note, when Horrible breaks his own rules and tries to kill his adversary, Captain Hammer. Instead, the resulting explosion kills Horrible's love interest. The final montage shows a dead-eyed Doctor succeeding at everything he ever thought he wanted, concluding with Harris singing into the camera "I can't feel... a thing."
6 The Joker Can't Cross That Ledge
Alan Moore's influential Killing Joke introduced an era where The Joker knew no limits. He kills, tortures, and possibly rapes just to make a point. He ultimately fails, though, and is cornered by the Dark Knight who doesn't offer the usual beating. Instead, he reaches out to The Joker, says he understands true darkness, and maybe they can help each other.
In a strange, sincere moment, The Joker replies with a joke. His anecdote is about escapees from an asylum. When one patient offers to turn on a light and guide the other across a ledge, the second man is too afraid of being betrayed to join the first in freedom. That's The Joker, alone and afraid on his side of the ledge, forever.
5 Kite Man Is The Butt of the Riddler's Joke
Kite Man's long been one of those Batman villains readers like to laugh at. He's like the Penny Pilferer, like Firebug without fire. Another Gotham weirdo with a gimmick. Crime kites. A prominent role in The War of Jokes and Riddles helped give the character some credibility. Not only does he end up tipping the scales in the Joker's favor, but he also has a heart-wrenching backstory.
Nygma killed his kite-loving son, and he became Kite Man in his child's honor. Any dignity the character gained is stripped away by the Riddler's closing explanation, though. He chose Kite Man, set him up to be an ineffectual supervillain. Riddler killed the man's son trying to make the Joker laugh, a moment so terrible that Batman tries to stab Nygma to death.
4 Miss Lint Meets The Terror
Amazon Prime's take on the Ben Edlund classic, The Tick, does a great job humanizing its funny heroes and villains. Miss Lint is a new character, a lightning lady who survived her villain-mentor's death. Throughout the first season, Yara Martinez puts in an amazing performance as the deadly, hilarious, and sad villain whose static electricity powers make her a magnet for dust and lint.
This dynamic reached a crescendo when Lint discovered her mentor, The Terror, faked his death a decade ago and didn't bother to tell her. She's been wandering in the wilderness ever since. As time goes by she realizes how little she meant to The Terror, and the biggest letdown comes when she realizes the supposedly brilliant villain is actually just mean and obsessed.
3 Kingpin Loses His Family... Again
Perhaps the greatest Spider-Man film Into the Spider-Verse introduces a host of animated villains: The Green Goblin, Prowler, Olivia Octavius. Towering above them all is the film's antagonist, the dapper and brutish Kingpin, who's funding experiments exploring alternate dimensions.
The audience gets to see Fisk's motives, though, and it's heartbreaking. His wife and son caught him in a murderous fight with Spider-Man and fled, dying in a car chase while trying to get away from him. He's willing to risk the universe to bring them back. He almost succeeds, but his alternate family abandons him AGAIN when they see him trying to squash Spider-Man.
2 The Luthor/Brainiac Team
Alan Moore earns a second spot on this list for Whatever Happened to the Man of Tomorrow? This pre-Elseworlds "imaginary story" features sad villains galore, including a suicidal Bizarro, and a messily killed Mxyzptlk. The saddest of the lot is Lex Luthor, who tracks down Brainiac's body intending to revive the android. Brainiac is in a hurry, though, and simply takes over Luthor's body as his host.
Luthor's eyes widen in horror as is body is stolen, and Brainiac intones humorously "Welcome to the new Luthor/Brainiac team." This plot played out differently in Justice League Unlimited where Luthor liked his new enhanced body, even if he didn't consent to it. In the original, though, he's lost all agency, a vehicle for a mad alien robot.
1 Ozymandias Learns It Isn't The End
Ozymandias isn't a good guy. In Watchmen he literally killed millions in a fake, Orson Wells style invasion. It was a far-fetched, self-absorbed plan that bet everything on one man knowing better than everyone else. But he hoped it would save the world. In the aftermath, the distant and god-like Doctor Manhattan and Ozy have a strange conversation. "I did right, didn't I?" the man asks the blue atomic god he'd recently tried to murder. "In the end?"
Manhattan's response is typically cold, if not unfeeling. "Nothing ends Adrian. Nothing ever ends." Veidt realizes he's talking to a man who sees the future, that the story isn't over. Adrian Veidt's arrogance killed millions, and only afterwards he realizes he hasn't saved the world. Ozymandius' victims are in a worse place, but there's infinite sadness in the man who repents an hour too late.