In G.I. Joe: Resolute, Cobra Commander has clearly been watching all his old episodes and taking notes (he even lampshades this on several occasions). Fortunately, he still manages to be incredibly entertaining since, despite being significantly more murderous, he's still completely bonkers.
In every Popeye cartoon, Popeye will eat spinach for some instant muscle power. Sometimes, though, Bluto will knock the can out of his hand at the last second, preventing Popeye from getting a single morsel into his mouth. In fact, in one cartoon, Bluto invented a formula that destroyed all the world's spinach, leaving Popeye at Bluto's mercy (or, his lack thereof). Fortunately, the audience intervened.
Azula isn't convinced when she notices a large dust cloud and is told that It's Probably Nothing. In the second season finale she attacks and nearly kills Aang in the middle of his Transformation Sequence! Upon hearing No One Could Survive That, she assumes he did survive. In the Grand Finale, Zuko attempts to pull a Batman Gambit on Azula to get her to shoot lightning at him; even in her insanity, she instead shoots the lightning at Katara, causing Zuko to take the blow for her. She has had occasional moments of genre-blindness but always learns from them. She initially had a Redshirt Army, but instead traded it for a Quirky Miniboss Squad after one screws up her plan, and after she tried to go after Aang alone, her next attempt was accompanied by her brother and a squad of secret police. Yet, for all her intelligence, she never learns not toKick the Dog or not to trust the smirking Evil Overlord who's screwed over your sibling. Mai and Ty Lee make this clear to her after it's too late for her to do anything about it.
Long Feng is Dangerously Genre Savvy in his own right. He has the entire Earth Kingdom wrapped around his finger by manipulating the incredibly sheltered Earth King. He also has control over the Dai Li police force, which comes in very handy when he is reminded in prison that they are still loyal to him, allowing him to make his escape. Unfortunately for him, he makes the mistake of believing that he can achieve absolute power on his own... which leaves an opening in his master plan for conquering Ba Sing Se that Azula takes full advantage of.
The Avatar comic book series The Search reveals Azula inherited/learned this from her father. When Ozai's hired hitman tells him his target was last seen disappearing in a dangerous, haunted forest and must be dead already since No One Could Survive That, Ozai doesn't agree even for a second.
In Sequel SeriesThe Legend of Korra, Amon is this for pretty much the whole first season. The only mistakes that he made came from his lack of experience with airbending and basic survival instincts.
Then we have Sato, who in his Face-Heel Turn, created an army of Mechas for Amon, making sure that they were Metalbender proof. He also led Tenzin, Lin, and Korra into a trap. This led to putting up a solid platinum wall, which was also Metalbender proof.
Malware is a big example, he learns from his mistakes and is quick to fight dirty and exploit his enemy's weaknesses, like Ben's Chronic Hero Syndrome.
Kyhber also fits, he waited until Ben didn't have any backup before trying to catch him, and attempted to defy the Villain Ball.
Albedo. After he captures Ben, he leaves bits of his DNA (hairs, nail clippings, etc.) scattered across the galaxy (since he and Ben have the same DNA in Albedo's human form, the Plumbers can't use DNA tracking to find Ben now).
Then, when Max and Rook track him down anyway, he reveals he had a trap already set up.
Earlier, when impersonating Ben, he used Rook's hopes that Ben would listen to his advice to keep him from thinking too deeply of any Out of Character moments.
The foolish and incredibly Genre Blind villain Abis Mal was partnered with an assistant named Haroud who was incredibly Genre Savvy, but his intelligent suggestions were usually shot down by his boss' hubris and lack of foresight.
This is part of Mozenrath's Character Development. He starts out Savvy enough to quickly learn what exactly Aladdin will or won't risk his life for, yet he's still prone to Evil Gloating, Death Traps and not foreseeing that another villain might double cross him. It doesn't take long though before he subverts the classic tale by kidnapping the hero instead of the princess, and he knows enough about magic to get the drop on the heroes time after time. He also realises that the heroes won't just hand over Genie for Aladdin's life, so he lures them to where his secret weapon is stored. In a later episode he also points out how he could be gloating, but chooses not to, manages to foresee Aladdin's sneak attack after he was told that the hero was dead and proceeds to kick their asses, one after the other. They only won that time because they had additional help.
In "Rufus in Show": Falsetto Jones puts Kim and Ron in a Death Trap... and sticks around to watch it work! (He may still be a Harmless Villain, but even Kim warns him how dire a breach of tradition this is.)
Ron was also this both times when he was accidentally turned evil. So much so that he knew well enough to scan for the frequency of Kim's kimmunicator as well as set up a decoy plan to distract her from his real goal. The second time, he mocked another villain for not realizing the full potential of her plan: if you can turn people evil with a ray, the very first person at whom that ray should be pointed is the hero.
The Venture Bros.: The Monarch's whole character is his conflict and frustration between his dangerous genre savvyness and his very literal Contractual Genre Blindness. However, everyone else suffers from Contractual Genre Blindness, and the one enemy that didn't (Jonas Venture Jr.) thoroughly kicked his ass (and was just going to kill him) before being informed about guild rules and how a man with a private army with wings and a giant flying cocoon would be extremely dangerous if he ever got tired of being defeated too quickly and started committing real crimes.
Monarch's henchmen #21 and #24 have been through so many catastrophic failures in the past and lived to learn from them that they have become practically indestructible. They brag about this fact to henchman #1 while on a mission to Spiderskull Island, explaining in detail every single trope and convention that #1 blindly leaps into and how horribly he will die as a result while they walk away unscathed. They are right, correctly predicting that he gets slaughtered by Brock Sampson while they use the oldest trick in the book to avoid him, pretending to be mannequins in the Jonas Venture museum exhibition room and later commenting how cliche that was.
This is best explained by 21 and 24 themselves:
Henchman 21: You still don't get it. 24 and I have been on, like, a thousand missions. We've been shot at, dipped in acid... Henchman 24: Brock Samson hit me with a car. Drove right into my kidney. Here I am! Henchman 21: Yeah, we can walk across this floor and nothing would hit us. But then like this huge log would swing down and take your head off. Henchman 24: Hey, here; what's your name? Henchman 1: Henchman number 1. Henchman 24: See, you are nameless. Henchman 1: I'm Scott Hall, my name is Scott Hall. Okay? Henchman 24: No, won't help. Henchman 21: Yeah, now it's just pathos. So you're dying in my lap and I'm all "Scott! Scott, don't you quit on us! Don't you dare!!" Henchman 24: You just made your unavoidable death more pathetic.
Transformers Prime Megatron started display heavy amounts of this as the series went on. When Optimus Prime loses part of his memory in "One Shall Rise", Megatron took over measure he could to maintain the charade of not being evil, but knew still Optimus would see through it eventually. Unfortunately for him, it happened sooner than he planned due Starscream breaking onto his ship. Finds another Starscream in his ranks in the form of Airachnid, moves to have her killed immediately. Confronted by 4 clones of Starscream in "Armada", he knows that they're all power hungry backstabbers like the original and tries to turn them on each other. It doesn't work, but it came close.
Starscream is quite Dangerously Genre Savvy as well. In one episode, Megatron is buried under tons of rubble, and Starscream starts with his "Megatron is dead, I am in charge" gloating... but he stops mid-gloating and lampshades that Megatron has a tendency to survive stuff like that, and that it'd be in his best interest to attempt to rescue him to avoid his wrath.
And adding to that, seeing Megatron and Starscream going head-to-head in the savviness department is a treat. The episode Patch is all about Megs and Scream trying to outsavvy each other over whether Scream rejoins the Decepticons or Megs blows him the hell up.
The Season 2 Finale is the golden moment for Megatron. When Optimus destroys the Omega Lock, he does not break down in outrage for two reasons: 1) He knows what the implications of Optimus' actions are, and how he can turn them in his favour, and 2) he already discovered the Autobots' base.
When Predaking reveals his sentience and expresses his desire to lead the Predacons, Megatron immediately realizes he has a potential insurrection on his hands. Starscream's plan is pure genius: instead of dealing with the problem themselves, they simply leak the location of Project Predacon to the Autobots and let them handle it. The end result? A potential rebellion thwarted, a disarmed (literally and figuratively) Autobot, an even more fiercely loyal Super Soldier, and a discovery that leads to an even greater plan than was abandoned.
Starscream finally shows his colors and attempted to blow him up, only to try and weasel his way back into Megatron's grace when it is more profitable. He promptly terminated him on the spot. Starscream somehow turns up again for revenge? Megs kept his cool struck him down and this time checked his spark chamber(equivalent of checking a pulse) to be sure. Starscream turns up AGAIN and manages to have the upper hand? Tolerated him until he loses said advantage, used him as a tool after that and promptly dealt with him the moment it looked like he could be a threat.
Other non Starscream-related examples include: Playing up a masquerade of being a benevolent badly wounded autobot when he awakens practically dismantled across an alien(human)'s lab and fooling said human into rebuilding him in secrecy while simultaneously trying to undermine and kill the autobots on Earth. After regaining his body though failing to acquire the Allspark. He hides in secrecy, having had cloaking devices put on him and his crew to hide while having a device built to transport his behind enemy lines.
David Xanatos of Gargoyles usually refrains from underestimating his opponents, knows the actual capabilities of his Mooks, will not test the immortality potion on himself, refuses to seek revenge on his enemies as it's a 'sucker's game', and he never crosses the Moral Event Horizon that would keep the Gargoyles from working with him in extreme situations.
Also, all those plans mentioned on this page so far that benefit the planner in some way whether they succeed or fail? TROPE.NAMER.
The X's: The relationship between supervillain Glowface and right hand man Lorenzo Suave is the same as Abis Mal and his henchman Haroud in Aladdin: The Animated Series. He is much more intelligent than his master, who tends to hatch up idiotic schemes like building a giant ray gun to bring the Eiffel Tower and Big Ben to life in order for them to wrestle so he can sell tickets. In fact Lorenzo is actually is the most normal of the tv series' villains - when Glowface was sick as well as other S.N.A.F.U. agents, he proved to be a better villain than Glowface or any of the other members.
In the episode "The Clock King" we have Temple Fugate, the Clock King, who knows Batman will use certain tropes, and he takes steps to foil them:
Batman always appears in time to foil the Evil Plan, so he simply enacts it and waits for Batman to appear preparing his Train Escape.
Batman is a Great Detective, and he manages to easily figure out where Fugate is hiding and what he's planning next. Fugate, anticipating such, deliberately leaves clues that lead Batman to find his hideout, determine his plans, and then, either delay him for put him into one of several death traps.
Eddie G. and the rest of the mooks had to pick a drug shipment, but he knows the Batman will give them a Mook Horror Show. To avoid this, Eddie sets Sidney up as bait so Batman will be too busy with Sidney to notice them.
Batman knows that Sid has Karmic Protection by bitter experience so instead of harming Sid for being one of the mooks, he sends him to Jail knowing fully that is the only place he will be safe and satisfied his dream to be a big shot.
In Justice League, the Joker, as usual. He even has some fun doing so in the episode "Wild Cards" by quipping "It's obvious he hasn't watched enough TV," when Green Lantern is taken out from behind with a shot from the Royal Flush Gang's King.
The majority of the villains in Young Justice have been very pragmatic, manipulative, and exceedingly Genre Savvy. Doctor Desmond immediately realized the threat represented by the team of meddling kids and took steps to have them copied and eliminated. His only mistake was miscalculating how much free will the Superboy clone and the rest of his minions had. His employers, the Light, take it the next level and constantly use the League's heroics and interference to their own advantage. What do you expect from villains created by Greg Weisman?
The Batman episode "Gotham's Ultimate Criminal Mastermind" features an AI called the Digitally Advanced Villain Emulator (D.A.V.E), who was programmed to be Genre Savvy, his personality being a blend of various villains, and he anticipates and counters everything Batman throws at him. For example, after their first fight, Batman surreptitiously sticks a tracker on him. Their next encounter begins with this gem of a line:
D.A.V.E: "You probably want your tracking device back? Another predictable move." Batman: "Then my next move won't surprise you either." (For the record, it didn't.)
You probably want to know how I uncovered your secret. It was simple, really. Using information readily available to anyone, I began by narrowing down my search through Gotham's population of 750, 832 males. Those not falling inside Batman's probable age of 18 to 36 were eliminated. Medical records revealed body type matches. Tax records indicated those who possess the wealth and resources to create his technology. But the true key to the puzzle was deducing who of the remaining candidates had motive to become the Batman. After all, every great hero must have an origin. And when Gotham's Ultimate Criminal Mastermind put it all together, the answer was obvious; Bruce Wayne, son of the late Thomas and Martha Wayne.
Gibbs in Titan Maximum has one such moment at the end of the first season. When the heroes manage to deactivate the timer for his bomb and beat him up, Gibbs just remote-detonates the thing and escapes while they're celebrating.
Gibbs: "Enjoy your teammate friendship asslickin' kum-ba-ya bullshit while I just go ahead and win."
This is even more impressive because the bomb was located inside an energy beam that rendered it virtually inaccessible. The bomb and method of placement were both specially built specifically so it could survive inside the beam. It would have been very easy for Gibbs to assume the bomb would not have been deactivatable.
Psycho of Toxic Crusaders has the uncanny ability to perfectly predict what will happen later in the episode, every single episode. His boss always refuses to believe him.
Norman Osborn outdoes Tombstone, being the one to dethrone him. Plus, there's the part where he tricks Spidey into thinking that his son Harry is the Green Goblin by faking a limp, dressing his son Harry (who has been taking the Goblin formula as Spidey knows well) as the Goblin, and then breaks his son's leg to make it look like the Goblin Spidey's been fighting all this time was Harry. He also hires the Chameleon to impersonate him so he has an alibi. In the penultimate episode, after his identity has been outed, he fakes his own death in a case of Know When to Fold 'Em.
Even Rhino has his moments - he immediately deduces that if Peter Parker is always getting photos of Spider-Man, they must have some sort of connection and the best way to get latter is through former. And he used one of Spidey's own tactics against him.
Doctor Octopus also gets in on it. In his first encounter, he is smart enough to flee when his battery is low, and deduces what Spider-Man is up to when he tries to run the clock out again. His second appearance, he's made sure that he - and the rest of the Sinister Six - have all come up with counters to how they were defeated before (His battery is harder to reach, Vulture's flght suit is armored, Electro has learned how to handle water, etc). When that fails, he pretends to turn a new page and spends the rest of the series plotting Spider-Man's demise from comfort in the mental institute for the criminally insane.
The Brain for most of his appearances as Teen Titans Season Five's Big Bad- in the opening two-parter, he loses only because Beast Boy is Crazy Awesome and therefore unpredictable; in subsequent episodes he sharpens his game and ends up predicting his enemies' moves like clockwork. Unfortunately for him, he suddenly becomes Genre Blind in the final episode, forgetting to have his minions check for bodies or considering that they might fall prey to the Conservation of Ninjutsu until it was too late. He also, once more, fell victim to Beast Boy's Crazy Awesome as well at that point.
The Lich from Adventure Time. There's a reason It Only Works Once on him: he goes out of his way to prevent you from using the same thing on him twice. He was also smart enough to avoid a direct fight with Finn and Jake until he had the chance to regain at least some of his strength.
Doubly illustrated in the Lich's second appearance. He knew that Finn could resist his Mind Control, and predicted that by giving Finn the opposite command of what he really wanted him to do while under the control, he would get Finn to do exactly what he wanted.
The Mega Man cartoon had a couple instances of this.
In "The Big Shake", Wily discovered Light and Megaman were working on a device to stop his earthquake machine. His response was to direct a maximum-powered earthquake directly at Light's lab in an attempt to kill them all, or at the very least wreck the machine.
In "Campus Commandos", Protoman shot Mega's Arm Cannon while he was distracted, breaking it for about half the episode.
In "Future Shock", Wily is aware that if Megaman makes it to the time machine, his conquest of the future will end. So he orders Protoman to rig it to explode.
Unlike other robots who panic after Mega Man does what he is known for, Pharaoh Man doesn't stand around. After he spouts his catchphrase, Pharaoh Man punches him.
A couple of Wily's death traps were fairly genre-savvy; the robots have attempted to kill Mega while he's weakened or unconscious, and in "Brain Bots" Megaman was handcuffed to the floor as a spiked ceiling descended on him.
This occurrence in "Robo-Spider":
Wily: I've got to turn up the power... Wait, what am I worrying about? There's no way Megaman can stop my Robo-Spider! *pause* Wily: I'm not taking any chances. *turns up power*
Upon discovering Dr. Light made an antidote to his retrograde virus in "Robosaur Park", Wily immediately decides to destroy it. After Mega intervenes and they play keep-away with the antidote, it ends up back in Wily's hands. Wily then hops in the Skullker to fly away from the heroes, and destroy the antidote someplace where they can't interfere.
In The Fairly OddParents episode "Emotion Commotion", Timmy becomes this when he wishes he had no emotions, even going as far as to pointing out that they couldn't build a boat in Gilligan's Island because it would end the series. Also Crocker can be this from time to time, mainly in the specials.
Technus in Danny Phantom, who was known for his Genre Blindness, surprisingly became this in his third appearance when he refused to shout out his plan, even though he briefly went back into it towards the end of the episode. In his fourth main appearance, his savviness improved so much that he knew to use Danny's feelings for Valerie to distract him while he attempted to gain access to a satellite which would allow him to control every machine on the planet, send Valerie's suit under his control after him so that when he wasted it, it would hurt Valerie, and give Valerie a new, improved suit so that she could keep him busy while he took control of all technology. His only mistake was not realizing how upset Danny would be for inadvertently hurting Valerie.
Afterwards, he can't simply "discordate" Twilight Sparkle, as her Element ("the most powerful and elusive Element: Magic" in his own words) doesn't have an obvious opposite. So he... does nothing. No, he just sits back and watches as the torment from her twisted friends, the chaos inflicted on Ponyville, and the Elements of Harmony failing to activate drives her off the Despair Event Horizon, breaking all by herself. Ultimately, the only thing he did wrong was being over-confident (and Celestia having a backup plan).
Discord demonstrates this again in "Keep Calm and Flutter On". He uses Fluttershy's Friend to All Living Things nature to drive a wedge between her and her friends (so she wouldn't use her Element against him), getting her to defend his "nice" self from her "mean" friends, which works even though Fluttershy knows he's doing it. Meanwhile, he has two other backup plans going at the same time, one of which relies on him deducing (correctly) that Twilight might attempt a Heel-Face Brainwashing on him. Fortunately, he forgot how strong The Power of Friendship is, strong enough to affect even him.
And props to Fluttershy on that one as well, for knowing exactly what Discord was doing and letting him think it was working, when really she knew it would backfire on him because The Power of Friendship is just that powerful.
The Power of Love is almost as potent as The Power of Friendship in Equestria, so along come the changelings, beings who feed on love to make themselves very powerful. Their queen not only impersonates a Love Goddess so she receives a lot of love, but organises their invasion to coincide with a wedding, ensuring that there is plenty of love going around on which to feast. As she sings herself: "This day is going to be perfect~".
King Sombra was smart enough to take advantage of his own status as The Dreaded by hiding the one thing that could stop him in the heart of his own fortress. Then he made sure unicorn magic was needed (all of his former slaves are Earth ponies). On top of that the Unicorn would have to know how to use dark magic, which most unicorns don't. Then he added a bunch of traps on top of that. The only reason he lost was because of a little tag-a-long dragon.
The Garden Snake from American Dad! rigs a building to explode, and in order to keep everyone inside, he rigs every single possible exit he can imagine, which covers a lot of ground. He also set the explosives on a locked timer so the CIA wouldn't be able to kill him. Otherwise they'd be left with no way to stop the bomb. He also kept the CIA busy with false demands, having no real intent of stopping his plan for whatever reason. He explains that, since his religion forbids so many other forms of entertainment, he's had a lot of time to watch movies and learn from the mistakes other fictional terrorists make.
Parodied in an episode of The Adventures of Sonic the Hedgehog. Grounder, who is usually an idiot, has become super smart resulting in him becoming very Genre Savvy and he ends up nearly defeating Sonic once and for all. What ultimately foils his plan? His fellow mook Scratch, who is too Genre Blind to realize that he'll just screw up everything, ruins Grounder's entire plan in a half-assed attempt to help out. He does this despite the fact that the whole time Grounder is flat out yelling at him not to get involved and is repeatedly telling Scratch he doesn't need any help.
XANA from Code Lyoko was occasionnally Genre Blind, but would usually be quick to learn from his mistakes, and before that he would display surprising amount of genre savvyness occasionally.
Belphegor from the animated series "Belphegor" is rarely, if ever, caught off guard by something that the other characters plan or use to capture him. At one point he even lampshades this at a general he's after, when the latter tries to use a Trap Door on him. Said trap door was already reconstructed and deactivated by Belphegor before he arrived to face the general, and he later uses it as a lowering platform to escape the police. It helps that Belphegor is a Diabolical Mastermind.
Adventures of the Galaxy Rangers: the Queen of the Crowns isn't usually genre savvy, she had her moments. In "Shoot-Out," she made it widely known to every gunslinger in the galaxy that she was offering a fortune as the grand prize in a gunslinging tournament. This gets every thug from Mars to Tortuna interested, but just to sweeten the pot, she says she'll also throw in Eliza Foxx's psychocrystal specifically to lure the Rangers in. Sure enough, the Rangers show up and put Goose (their best gunslinger) in under an incredibly obvious alias just to troll her right back. Meanwhile, she had a trap set around the trophy to catch the other three Rangers when they tried to steal it. Topping it off - the prize was totally bogus. So, she ended up with a fresh supply of people to melt down for Life Energy in her Mook Maker, and she very nearly had the entire Series 5 team, who ended up getting away with virtually nothing.
Taurus Bulba demonstrates this trope a bit, knowing that the title character and Gosalyn aren't dead, knowing exactly how egotistical Darkwing is and how to use that against him, and when he knows that Darkwing has the code despite having no real proof, he essentially takes advantage of the attachment that Darkwing has of Gosalyn, threatening to drop her off a building if he doesn't spill anything about the code.
Negaduck also frequently demonstrated this trope (which was part of what made him one of Darkwing's most dangerous villains). Most notably in the "Just Us Justice Ducks" two-parter. He even intentionally leaves behind an impossibly obscure piece of evidence to lead Darkwing to his hideout, because he knew Darkwing "wouldn't notice the enormous flag." Considering this came right after Darkwing missing the flag seemed like a throwaway joke, this makes the savviness all the more impactful (and hilarious).
Lex Luthor in Superman: The Animated Series had made contact with Brainiac, who said was going to give Lex Corp tons of alien knowledge. Superman came and pleaded that this could be a giant trap, at which point Lex revealed he had automated missile sites pointed at Braniac's ship. When Braniac hacked into Lex Luthor's systems, we also learn that the missiles were not connected to Lex Corp computer systems because they fired at Braniac's ship (though Brainiac quickly retaliated and destroyed some of the launchers, the missiles did bring the ship down).
In Bugs Bunny Nips The Nips, a Japanese soldier is presented trying to attack Bugs and rambling in incoherent Japanese. When Bugs impersonates a Japanese general, the soldier tries to commit hari-kari when he almost kills him, but then Bugs gives himself away by eating a carrot. He then tells the audience "Ooh, that no Japanese general. That Bugs Bunny. I see him in Walner Blothers-Reon Schresinger-Mellie Merodies cartoon picture. Oh, he no fool me!" The soldier then goes up and stands next to the disguised Bugs, pulls out his own carrot and performs Bugs's usual schtick, saying "Eh, what's up, Honorable Doc?". This takes Bugs completely by surprise and the chase resumes.
Miles Dredd in Max Steel 2013 shows a remarkable amount of Savvy towards the end of the season. All episode, N-Tek tries to figure out how the missiles Dredd has taken control of are supposed to factor into his plans, since they aren't powerful enough to achieve any known goal. At the climax, they realize the missiles had no point except to trick Max into trying to destroy them with TURBO energy. The missiles destroy themselves, freeing the TURBO energy to blow up the defense system protecting Earth from the Makino Empire. Oops.
Henna in Barbie Mariposa. She continuously poisons the Queen, gloats only when she thinks she's alone, manipulates Lord Gastrous into doing her bidding by giving Anti-Advice, tries to stall Mariposa from healing Marabella, controls the Skeezites so they won't eat her, stops at the beginning of a Motive Rant when she sees Mariposa has the antidote, and manages to steal back the antidote from Mariposa, then destroys it. She's only defeated by a margin of two seconds.