The most diabolically clever thing an evil character ever did

I was just thinking about starting a somewhat similar thread, although the example I have in mind is brilliant in a totally different way.

MASSIVE SPOILERS FOR The Wire, which is the greatest TV show in the history of humanity, so you should not read these spoilers unless you’ve already seen it:

In season 2 (or maybe early season 3?), drug kingpin Avon Barksdale has several problems:
(1) he’s in prison, although on a fairly short sentence as these things go
(2) his nephew D’Angelo is also in the same prison, and Avon is worried that D’Angelo, who is no way as tough as Avon, is starting to do heroin himself, a big no-no. Plus, D’Angelo isn’t totally trusted not to betray the family, so any sign of weakness is very worrying.
(3) Avon’s trusted lieutenant Wee-Bey is also in prison, and is being treated very badly by one of the guards, for reasons of a personal vendetta
So what does Avon do?

He uses his contacts on the outside to smuggle some poisoned heroin into the prison, and to plant some in the car of the guard with the vendetta.

So if D’Angelo is really taking heroin, he’ll die, and in a way that in no way seems linked to Avon himself. Because the guard is blamed for the smuggling, he’s arrested and is no longer a bother to Wee-Bey. And, best part, Avon is the one who tips off the authorities about the heroin hidden in the car… so this “cooperation” allows him to get out earlier on good behavior.

So many birds, one stone.

Princess Leia: No! Alderaan is peaceful! We have no weapons, you can’t possibly…
Governor Tarkin: [impatiently] You would prefer another target, a military target? Then name the system! I grow tired of asking this so it will be the last time: Where is the rebel base?
Princess Leia: …Dantooine. They’re on Dantooine.
Governor Tarkin: There. You see, Lord Vader, she can be reasonable. Continue with the operation; you may fire when ready.
Princess Leia: WHAT?
Governor Tarkin: You’re far too trusting. Dantooine is too remote to make an effective demonstration - but don’t worry; we will deal with your rebel friends soon enough.
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Obi-Wan: I felt a great disturbance in the Force, as if millions of voices suddenly cried out in terror and were suddenly silenced. I fear something terrible has happened.

Khan’s “Perhaps I no longer need to try” speech has always impressed me because he doesn’t fall into the standard bad-guy trope of letting himself get goaded. He’s prepared to declare victory and move on, leaving Kirk impotently “KHANNNing” his head off.

Later on, of course…

And in the main comic, we have Xykon’s condensed little horror show: Follow the bouncing ball, children.. What makes it even worse is that you could actually do that in D&D, or so I’ve heard. Really, he summarizes it better than I ever could:

pied piper of hamlin.

Actually,

  1. Michael never “loses interest” in the family business, nor does he pretend to.
  2. Tessio, Barzini, Tattaglia, and the heads of the other 5 families were killed prior to Carlos’ confession. They were all killed (except for Tessio) during the baptism sequence (to the tune of Bach’s Passacaglia in C-Minor). This was done to give Michael an obvious alibi and to put Carlos off his guard. Tessio was killed after the baptism, but right before Carlos.

But it’s even worse in some ways, because…

Xykon may overestimate the hold he has over Redcloak, who may be even more bastardly than he. Redlcoak has no emotionality behind it (whereas Xykon is all for his personal pleasures and kicks), but he’s prepared to end the universe so his god can go back to the bargaining table with the other deities.

I think Sauron allowing himself to be taken prisoner by the Numenoreans showed a (literally) diabolical level of cleverness and evil intent.

Dollhouse

Convince everyone that you are just pimps, when really you are planning to steal pretty people’s bodies so you can be immortal.

Pee Wee Herman creating that alter-ego Paul Reubens who decided to derail a lucrative career by doing the five knuckle shuffle to Nurse Nancy in a seedy Florida movie theatre.

Was he really looking to off D’Angelo or was he looking to kill the person who he thought was getting him hooked? Seems to me if he didn’t care if D’Angelo died he wouldn’t have got into it with Stringer when Stringer had him whacked.

I personally thought the Pencil Trick was stupid, but the whole original “off the accomplices as they become expendable” plan in the very beginning was pretty cunning.

That’s not clever at all, just a stock villain trick. He might as well have been twirling his moustache as he said it.

you really should spoil it, for those of us who would like to know and dont always have access to neat movies …

Except that his stupid plan ends up revealing his identity to the whole world by giving a day long interview in a police station filled with video cameras, by telling a story that, while initially confusing, ends up confirming his identity to the police officers.

Of course that’s only if he is to be believed at all. The only thing the audience knows for sure is that he may have been involved in some way in shootout on a boat. Everything else is made up. He might have just been a common hood who turned on some comrades in a heist gone bad. If the dying criminal was mistaken or lying (both could be expected considering the circumstances) then Verbal could also just be some random hood lucky enough to survive a firefight.

Overlord hijacking a space shuttle, dropping Zone Generators out of it, and turning half the Earth into the Spiral Zone. That’s pretty evil.

(still talking about The Wire)

I can’t say it’s 100% clear, but remember that right before that he’s worried that D’Angelo might be using. I think it’s a survival of the fittest type thing. And of course just because you’re willing to kill your own nephew doesn’t mean you’re OK if someone else does

I am always impressed by Darth Sidious’ plan to lead two factions in a war with each other the ultimate goal being the non violent take over the Republic.

Okay, here are MASSIVE spoilers for Oldboy. You asked for it–brace yourself:

[spoiler] A Korean businessman, Dae-sue, is on his way home from work to his wife and young daughter. He is abducted and imprisoned in what looks like a hotel room. He doesn’t know who did this to him or why. He is regularly provided with food and water, and sometimes he is gassed to put him to sleep. After some time, he learns from the television in the room that his wife has been murdered and his daughter has been sent to live with foster parents. Dae-sun is named as the prime suspect in his wife’s murder.

After 15 years of this imprisonment in the same room, he is set free but still he does not know who imprisoned him or why. He is a dazed and broken man and wanders into a restaurant and talks with a young woman, Mi-do, who works there. She pities him and takes him back to her home so she can take care of him.

Within the next day or two, the man who had imprisoned Dae-sun reveals himself. Dae-sun does not seem to know the man (named Woo-jin). Woo-jin makes a proposition to Dae-sun. If Dae-sun can discover the reason that Woo-jin imprisoned him (within 3 days or something like that) then Woo-jin will kill himself. If Dae-sun does not figure the mystery out, then Woo-jin will kill the young woman, Mi-do, with whom Dae-sun has become very close.

As Dae-sun and Mi-do begin investigating to unravel Woo-jin’s motives, they fall in love despite their large age difference and have hot, passionate sex. Like, “I’ve been locked in a room alone for 15 years-” sex. He really fucks the heck out of her! :slight_smile:

Their investigation soon reveals that Dae-sun and Woo-jin had attended the same high school for a brief time. Dae-sun eventually remembers that one day in school he had spied on Woo-jin and one of the girls from the school having sex in an empty classroom. Dae-sun had made some comments to some other students about Woo-jin and the girl, and the rumors had spread. Dae-sun, however, had transferred to another school and never knew the whole story: The girl that Woo-jin had been screwing was actually his own sister! This sister, disgraced by the rumors of incest and the truth behind them, had killed herself.

Dae-sun now confronts Woo-jin with this information, having solved the mystery, and tells Woo-jin to live up to the deal and kill himself. Instead, Woo-jin gives Dae-sun a photo album. Dae-sun opens the album and sees a photo of his own wife and young daughter, as they were the last time he saw them before being imprisoned. Then as he flips through the subsequent photos, his wife no longer appears (she was murdered, remember?) and the girl is growing older and older in the pictures. As she matures in the photos over the years, she starts to look familiar. The final photos show her as a young woman and Dae-sun realizes with horror that the daughter he hasn’t seen in 15 years is the young woman Mi-do! The same woman that he has been having hot monkey sex with! :eek: Aaauuugghhh!

Woo-jin had orchestrated everything–Dae-sun’s imprisonment, the death of his wife, and his release 15 years later–in order to set Dae-sun up to commit incest with his daughter. (there is a somewhat far-fetched story involving hypnosis to explain how Dae-sun first found Mi-do in the restaurant and why she fell in love with him)

Dae-sun is insane with grief. He begs Woo-jin not to tell Mi-do about this. He also begs Woo-jin for forgiveness. As a sign of his grief, he cuts off his own tongue! Really!–he hacks through it with a pair of scissors! :eek: :eek:

Woo-jin savors for a moment the success of his ultimate revenge, then gets in the elevator from his penthouse, pulls out a gun, and blows his own brains out.

Now *that *is an evil, diabolical plan.[/spoiler]

These are all pretty evil, but not “Diabolically clever.” To reach that level, it has to be a simple act with vast, tragic consequences that he(the villain) anticipated, but we did not. Like rolling a golf ball down a snowy mountain, resulting in an avalanche to the poor village below.

In comics: Thanos transports the Silver Surfer to the Tokyo subway, then immediately brings him to a pastoral alien planet, ostensibly to compare the two civilizations. Then he mentions that Surfer picked up some viruses in Tokyo that will kill half the alien world’s population, and leaves Surfer to figure out a way to minimize the tragedy. He tricked the noble Silver Surfer into decimating an entire race.

Okay, teleportation is pretty complicated stuff, but it’s a minor aspect of Thanos’ power, so it counts.