History BondVillainStupidity / WesternAnimation

** In a DeletedScene from "[[Recap/TheSimpsonsS5E10Springfield $pringfield]]", Homer's incompetence at the blackjack table gets James Bond captured by Blofeld. Bond asks Blofeld to at least tell him his EvilPlan but the villain said he wasn't going to fall for that again.

%%* {{Lampshade|Hanging}}d with Dr. Gene Splicer in the ''WesternAnimation/TinyToonAdventures'' episode "Hare Raising Night".

* In ''WesternAnimation/ThePerilsOfPenelopePitstop'', the Hooded Claw constantly tries to murder the eponymous heroine(ish) so that he inherits her fortune instead of her. The entire episodes are devised of the heroes foiling his extremely elaborate and overly complex homicide attempts. Probably the biggest reason he never succeeded was his [[BigHam enjoyment at explaining every little detail of each plan to Penelope herself]]; it always took at least three minutes, and it would either reveal a flaw in the design to her or give her some time to either free herself or get saved by the Ant Hill Mob. Subverted in several episodes, in which the Hooded Claw admits he enjoys setting up and explaining his death traps so much that he really isn't very interested in whether or not Penelope manages to escape: if she dies, he inherits the fortune, and if she escapes, he gets to set up another death trap, so for him, it's a win-win situation.

* ''WesternAnimation/{{Wakfu}}'':
** Rushu. Wanting to play games with the heroes gives them a chance to escape, [[spoiler:although Remington and Grany don't quite make it]].
** EvilAllAlong antagonist [[spoiler:Qilby]] has quite a bit of WhyDontYouJustShootHim tendency, but the prize winner is when he has Yugo at his mercy in the [[BlankWhiteVoid White Dimension]] and can easily leave him trapped there while he moves on to Emrub, but instead he offers to take Yugo with him to Emrub to meet his people and then trap him back in the White Dimension afterwards. Doing this only lowered [[spoiler:Qilby]]'s chances of convincing the Eliatropes to join him, to say nothing of how Yugo ''is'' the Eliatropes' rightful king.
* Possibly the biggest case of NearVillainVictory in ''WesternAnimation/HeManAndTheMastersOfTheUniverse2002'' was the three-part "Council of Evil" episode. Skeletor's plan had worked almost perfectly, had most of the heroes at his mercy and bringing Eternia to its DarkestHour to date. But his overconfidence and ego did him in. He specifically said that the reason he wasn't killing them right away was so they could ''witness'' his true victory, seizing Grayskull and the Elders' power. Not only did this mistake cost him, it served as a serious "wake up call" to the heroes, and paved the way for the plot of second [[ExecutiveMeddling (and unfortunately, last)]] season.
* Played straight in ''WesternAnimation/TheAdventuresOfJimmyNeutronBoyGenius''. In the ''Film/JamesBond'' parody "Operation: Rescue Jet Fusion", Jimmy and Jet are left in an elaborate death trap... and manage to escape.
* Shown clearly in ''WesternAnimation/TheFairlyOddParents'' when Mr. Crocker meets Norm the Genie. They both hold a deep hatred for Timmy Turner, and Norm suggests sending him to Mars, while Crocker tries out a horde of elaborate impractical traps.

* In ''WesternAnimation/ThePerilsOfPenelopePitstop'', the Hooded Claw constantly tries to murder the eponymous heroine(ish) so that he inherits her fortune instead of her. The entire episodes are devised of the heroes foiling his extremely elaborate and overly complex homicide attempts. Probably the biggest reason he never succeeded was his [[BigHam enjoyment at explaining every little detail of each plan to Penelope herself]]; it always took at least three minutes, and it would either reveal a flaw in the design to her or give her some time to either free herself or get saved by the Ant Hill Mob. Subverted in several episodes, in which the Hooded Claw admits he enjoys setting up and explaining his death traps so much that he really isn't very interested in whether or not Penelope manages to escape: if she dies, he inherits the fortune, and if she escapes, he gets to set up another death trap, so for him, it's a win-win situation.
* All the time in ''WesternAnimation/InspectorGadget''. The plot of any given episode has the villain du jour trying to put the titular inspector through increasingly elaborate {{death trap}}s [[ComplexityAddiction instead of, ya know, just shooting him]]. This was subverted in an episode once, where they attempt to simply poison him. However Brain, Gadget's dog, has discovered the plan and keeps him from eating ''anything''.

* {{Lampshade|Hanging}}d and {{averted|Trope}} in the first season finale of ''WesternAnimation/GeneratorRex''. When [[BigBad Van Kleiss]] gives the order [[spoiler: for [[TheDragon Biowolf]] to dispose of a [[BroughtDownToNormal depowered]] Rex]]. Rex asks him if he'd rather lock him a cage or tie him to a slab and use a slow moving laser on him, [[spoiler: Biowolf simply says "No", and tosses him out the window of [[AirborneAircraftCarrier the Keep]]]]. Interestingly enough, this is played straight later in the episode by the [[spoiler: {{Big|Good}} [[DesignatedHero "Good"]]]] of all people, who [[spoiler: chooses not to turn his electromagnet defense system high enough to tear the nanites out of Biowolf's body, but simply to immobilize him for a good old fashioned beat down]].
* Played straight in the ''WesternAnimation/SWATKats'' episode "Night of the Dark Kat", where Dark Kat and Hard Drive have managed to capture the eponymous heroes, but instead of summarily executing them, set them on the end of a long ConveyorBeltODoom that leads to a rock crushing machine, a machine which is wired to blow up the warehouse if shut down, leading to predictable consequences. Dark Kat usually proves smarter than that, too. Hard Drive even {{lampshade|Hanging}}s it: "[[StatingTheSimpleSolution I still say you should have let me fry those two!]]"

* ''WesternAnimation/SupermanTheAnimatedSeries'':
** In the episode "Where there's Smoke", one of the corrupt government agents seems to have the right idea at first, arming himself with a weapon that ''might'' hurt Superman. Unfortunately for him he feels the need to explain how it works and both threaten ''and'' insult the already pissed Man of Steel, painfully finding out -- when the incredibly fast hero crushes his wrist, disarming him -- that he ''really'' should have just fired it when he had the chance.
** In the three-part crossover with ''WesternAnimation/BatmanTheAnimatedSeries'', "World's Finest", the Joker comes to Gotham with a large chunk of Kryptonite, with a proposition for Luthor to kill Superman for a billion dollars. He manages to lure Superman into his trap, and even destroys his [[KryptoniteProofSuit lead suit]] that shields him from the radiation, but then he leaves Superman alone to die, [[GenreBlindness not realizing that Batman had followed him to Metropolis,]] who then saves Superman by destroying the Kryptonite.
* Maximus was prone to this in ''WesternAnimation/AtomicBetty'', although his excuse for why he didn't stay to watch the heroes drown in his flooding room trap was [[CatsHateWater "you know how I feel about water"]]. (Which indeed was the case in several episodes.)
* ''WesternAnimation/JusticeLeague'':
** Played straight in "[[Recap/JusticeLeagueS1E6And7TheEnemyBelow The Enemy Below]]" when [[spoiler:Aquaman's brother, Orm]] leaves ComicBook/{{Aquaman}} and his baby son pinned to a large piece of rock slowly sinking into lava rather than just killing them both outright.
** During "[[Recap/JusticeLeagueS1E8And9InjusticeForAll Injustice For All]]" Luthor and his group of Super Villains capture Batman, but instead of killing him right then they leave him tied up, which he uses to screw with them all and even finds a way to tell the League where they are. [[WhyDontYouJustShootHim Joker even lampshades the fact that they should no doubt kill Batman right away before he gets out,]] even pointing out how he himself has fallen into this trope himself several times and had it backfire. Naturally, it turns out Batman could have gotten out at any time [[NoodleIncident though how he does is never explained.]]
--->'''Joker:''' And they say ''I'm'' crazy.
** {{Lampshade|Hanging}}d in "[[Recap/JusticeLeagueS2E17And18SecretSociety The Secret Society]]," where the members of the League are kept in stasis after being defeated by Grodd's LegionOfDoom. Clayface, [[GenreSavvy a former actor]], asks why they don't just kill the captive heroes right now, and compares the situation to the mistakes made by the villains in the spy films he used to appear in. Note that Clayface is asking this while staring at ComicBook/MartianManhunter. This is especially unusual because [[spoiler:Clayface and Martian Manhunter are both Shapeshifters and the villains froze the wrong shifter by mistake. This means that Martian Manhunter in this scene is asking why the bad guys don't kill his allies. It could be he already knew this, as Martian Manhunter is also a telepath and probably got the plan from Grodd's thoughts, and is only asking out loud because Clayface isn't a telepath and would ask this]]. This gets Grodd to unwittingly spill his plans to the heroes before the plan is set into motion.
* ''WesternAnimation/{{Futurama}}'' pulls this with the Slurm Queen during the 'Fry and the Slurm Factory' episode. She has Leela in a vat of goo that will mutate her into another Slurm Queen, Bender on a conveyor belt headed for a metal recycler, and Fry stuck gobbling up a tub full of addictive soda, and then she and her guards leave them to their fates. Fry saves Leela by simply dragging the tub over to where she's being held and releasing her, then she saves Bender from being turned into soda cans. Luckily for the Slurm Queen, they don't end up telling the world where Slurm soda really comes from.
* Used and {{lampshade|Hanging}}d in the ''WesternAnimation/PhineasAndFerb'' episode "Nerdy Dancin'": Dr. Doofenshmirtz leaves Perry the Platypus shackled to a table with a slowly approaching laser beam, claiming, "I saw this in [[{{Film/Goldfinger}} a movie]] once. I didn't catch the ending, 'cause I had other things to do, but [[GenreBlindness it seemed pretty foolproof]]." Perry escapes as soon as Doof leaves, simply by slipping his small hands and feet out of the shackles.
* In ''WesternAnimation/TheLegendOfKorra'', Amon has Korra completely at his mercy with about two dozen of his [[EliteMooks chi-blockers]] restraining her and looks like he's about to take her bending away and... doesn't. However, he justifies it and only comes across as even smarter because of it. He needs support for his plan to succeed and this early in the game, taking her bending away would only turn her into a martyr banding everyone not already on his side against him.
* ''WesternAnimation/MyLittlePonyFriendshipIsMagic'':
** Discord, the second-season villain, makes this mistake ''twice''. He allows Twilight Sparkle to get her hooves on the Elements of Harmony, since he's corrupted the bearers and rendered them unable to use the Elements, and he leaves Twilight to her own devices in the unraveling Ponyville because he delights in her misery and helplessness. As such, when she regains her confidence, gets her friends back and fighting, and unleashes a devastatingly harmonious rainbow on his face, he's very much taken by surprise.
** In the episode "Read It and Weep", we are introduced to the ''JustForFun/DaringDo'' novels, which are mainly patterned after ''Indiana Jones'' and ''Tomb Raider''. As such, the main villain in the books, [[BigBad Ahuizotl,]] will often put the hero Daring Do into a clichéd DeathTrap. The example we see is of an ancient over-the-top execution machine involving spikes, [[TheWallsAreClosingIn encroaching walls,]] [[DrowningPit rising sand,]] and [[WhyDidItHaveToBeSnakes snakes and spiders.]] While it seems that Ahuizotl's confidence in Daring's demise is well-founded, he makes the classic mistake of leaving her to her doom, which allows her to use her pith helmet and some ImprobableAimingSkills to reverse the trap.
** In the season 4 episode "Daring Don't", Ahuizotl does it again by suspending Daring over a [[SharkPool slowly rising pit of water]] filled with {{piranha|Problem}}s. Given that the episode's premise is that everything in the ''Daring Do'' novels is actually [[RealAfterAll real]] (including Daring's previous escapes), he comes off less of a real threat and more of a villain with [[YoYoPlotPoint terrible amnesia]].
* ''WesternAnimation/BarbieLifeInTheDreamhouse'' has Closet, the AffablyEvil MasterComputer, exhibit this twice. First, he neglects to keep an eye on Franchise/{{Barbie}}, Midge, and Summer while gloating to Ken, allowing the three of them to ditch him through an AirVentPassageway. Later, Closet threatens to fry Barbie and her friends in a giant drier, only to hear the oven's timer go off. In response, he tells the girls not to move, then leaves to check on the crème brulee he's baking. The girls seize the opportunity to remove the Dreamhouse's CPU.
* ''WesternAnimation/GIJoeARealAmericanHero'':
** COBRA does this a lot, but one that stands out as ''especially'' stupid was the ChristmasEpisode. It started out like a good idea; Cobra Commander thought he'd attack the Joes' headquarters on Christmas Eve (worked for UsefulNotes/GeorgeWashington, right?) and it actually worked -- he and his men took the whole team of Joes hostage. Then the Commander got a good idea, ''maybe''. He had his men handcuff the prisoners and lock them up in their own meat locker, suspended from the hooks by their cuffs, then decided to take the Joes' vehicles for a joyride and attack a nearby city, maybe get the Joes in trouble. Then, however, Cobra Commander's last attempt at EvilGloating ruins the plan royally. He tells his prisoners he's leaving them a "Christmas present" and ''puts the keys to their handcuffs on a hook by the door'' before he leaves to taunt them, confident they can't possibly reach it. Unbeknownst to him, Shipwreck has already partially freed himself, getting down from the hook (he leaps up and grabs hold of it when they hear the Commander coming) so when the villain leaves again, freeing himself and the other is a simple matter. Even worse, when the villains leave with the Joes' vehicles, they ''leave their own vehicles behind'' (and apparently leave the keys in the ignitions, for that matter). Did the villains think the Joes wouldn't shoot down their own crafts? Wild Bill ''did'' say he felt "like [he] shot his own horse" when he did, but he still did, and so did the others. (So all this botched plan accomplished was to prove that COBRA can't claim that the Joes have better equipment as an excuse for their failures...)
** Ironically, during the five-part "Arise Serpentor Arise", when the villains took Sergeant Slaughter (likely one of the biggest thorns in their side) hostage, Cobra Commander was the smart one, wanting to kill him right away. Unfortunately for him, he had little control of the organization at the time, and Dr. Mindbender wanted to use Slaughter's DNA to supply the fighting expertise of his creation. It turned out ''very'' bad for them, and would be the biggest factor in the experiment creating just another failure of a leader.
* ComicBook/LexLuthor (often regarded as one of the worst offenders) actually subverts this in one ''WesternAnimation/{{Superfriends}}'' episode. He manages to subdue all the heroes except Superman in inescapable deathtraps that actually seem genuinely inescapable. (Even Batman is close to giving up). Then he reveals to his accomplice that this was part of his deal with a group of aliens that live in the sun itself; he gets rid of them, and they turn the sun red, leaving Superman powerless. They do so, and Superman is led to a nasty surprise, and Lex uses his final deathtrap on him. Thing is, Luthor is ''not'' being stupid this time. When the aliens double-cross him -- as he clearly feared they would -- he deactivates ''all'' the death traps with a single button on his vehicle, unleashing the heroes to deal with them. (Unfortunately for Lex, he's not as CrazyPrepared as he'd like; they still find him and haul him to jail after doing so.)
* ''WesternAnimation/Ben10Omniverse'' is ''filled'' with these:
** [[EvilGenius Dr. Psychobos]] manages to temporarily get Ben in his grasp in "Outbreak" when he comes to steal a piece of the Omnitrix from him, but chooses to let him live and just leaves once he gets said piece (which is replaced by the end of the episode). When called out for it by [[BigBad Malware]], he justifies his decision by saying [[UnderestimatingBadassery Ben isn't the real threat]].
** In "Vilgax Must Croak", Vilgax has Ben at his mercy, unconscious, in human form and defenseless, with everybody around unable to assist. He still decides to just escape his jail and leave Ben alive, even though it would have probably taken him a second at best to kill him.
** In "Frogs of War", the [[AliensAreBastards Inkurseans]] [[TheBadGuyWins manage to conquer Earth]] [[BoringButPractical with pure military might]] and force Ben into surrendering. Yet, rather than executing and putting him out of the picture permanently, they just exile him and send him into space, allowing him to come back later and [[spoiler:[[TheMole infiltrate them to end their invasion from the inside]]]]. Arguably justified in that [[spoiler:[[TheStarscream Attea]] [[BatmanGambit was counting on it]]]], but still, you gotta wonder why Emperor Milleus couldn't be more pragmatic.
** A particularly ridiculous offender with [[KnightTemplar the Rooters]], seeing how [[spoiler:their whole goal focuses around killing Ben to begin with]]. They had [[spoiler:him as their prisoner, in human form and unconscious]] ''right in their first episode'', but Proctor Servantis decides to [[spoiler:let him go]] and stick with his ridiculously convoluted plan (which by the way [[spoiler:[[VillainForgotToLevelGrind was developed to kill Ben]] ''[[VillainForgotToLevelGrind five years ago]]'', [[VillainForgotToLevelGrind and Ben has become much more powerful since then]]]]) on the argument that "he is tougher than he looks".
* What costs Bill his defeat in ''WesternAnimation/GravityFalls'' where Bill, rather than turning him into a tapestry like the other chosen ones, chooses to imprison Stan while he threatens the kids to blackmail Ford into giving him the equation that will break the barrier. To Bill, Ford won't give a damn if his brother gets tortured to death because Ford supposedly blamed Stan for screwing up the Zodiac, so there isn't any reason for him to keep Stanley. This bites him even harder because it's ultimately Stan''ley'' Pines who comes up with the idea to erase himself, along with Bill, once and for all.

* In the ''WesternAnimation/MegaManRubySpears'' cartoon, Dr. Wily and his Robot Masters have several moments where he could easily have destroyed Mega Man and/or his friends, but fails due to opting for an excessively elaborate plan:
** In "20,000 Leaks Under the Sea", after pulling off a clever EvilPlan, he managed to trap our heroes in a fake laboratory building that was in fact an enormous robot which then took them underwater. We later find out that he had a self-destruct for the building that he could've just used right at the start to kill them all before they even realized anything was wrong. Instead, he trapped them in an AgonyBeam while gloating about his plan, eventually leaving them to their fate, enabling them to make their escape. Not only that, but he apparently left some tools behind that Dr. Light was able to use to help them escape.
** In "Showdown at Red Gulch" the Robot Masters had Mega Man completely at their mercy after they knocked him out, but instead of finishing him off, they tied him to a horse and sent him off into the desert.
** In "Campus Commandos" the Robot Masters had Mega Man at their mercy, twice. The first time they locked him in a closet and the second time they tied him to gears in a clock and left him alone.
** In "Brain Bot" they handcuffed Mega Man to the floor and were going to crush him, but left him alone instead of staying to make sure he died.
* This is a signature trait of Black Heron in ''WesternAnimation/{{DuckTales|2017}}'', largely due to her borderline parodical status as a CardCarryingVillain:
** In the past, she was too focused on filming her "declaration of ill-intent" to take a young Beakley and Scrooge seriously, and she later is almost tricked into giving an evil monologue (but manages to catch herself).
** It's not really her fault that she leaked Bradford's true allegiance to the triplets since Bradford did not enact radio silence, and she was just doing her job trying to find him for extraction. Flying a helicopter with their organization's logo on the side clear and visible so that Scrooge himself can see? Absolutely. What's worse is that when Bradford expressed indignation at the screw-up, Heron sarcastically asked if he would've preferred she fly in an unmarked helicopter. Bradford, naturally, retorts with a big fat "YES!"
* ''WesternAnimation/MyLifeAsATeenageRobot'': Smytus's FatalFlaw is his obsession with EvilGloating and [[ComplexityAddiction grand theatrical schemes]], such as constantly putting time-wasting countdowns on his weapons for the sake of his ego. [[CharacterDevelopment He more or less grows out of it]] of it by the time of BigDamnMovie and [[NotSoHarmlessVillain nearly takes over the Earth as a result]], [[spoiler:only to be undone by one last bit of Bond-Villain Stupidity when he tries to use his SelfDestructMechanism to kill Jenny... [[HoistByHisOwnPetard only for her to safely hurl him far away from her because his self-destruct had yet another pointless time delay]].]]
* ''WesternAnimation/StarWarsCloneWars'': General Grievous has the heroes cornered, so naturally, being the CombatPragmatist he is ([[CharacterizationMarchesOn in this series, at least]]), he kills them, right? Nope. He instead launches into a dramatic speech about the futility of their persistence against him, which Shaak Ti ignores and [[CapeSnag ties his cape to a nearby train]] with the Force. Grievous is swiftly pulled away from the scene and has to expend extra effort trying to catch up.
* ''WesternAnimation/TheVentureBros'' features Red Death leaving rival supervillain Blind Rage ChainedToARailway, while explicitly lecturing him about how part of what he likes about that particular killing method is that [[HopeSpot it leaves a small possibility of escape]], meaning that the person will spend the whole time struggling in fear rather than resigning themselves to their fate. However, in this case, it's rather thoroughly justified, as Red Death's motivation isn't to kill Blind Rage (who is no real threat to him), but rather to send a message to his bosses--something that [[MortonsFork can be accomplished equally well]] by Blind Rage reporting back scared shitless or Blind Rage's corpse being splattered across the tracks.
* ''WesternAnimation/AvengersAssemble:'' One of several points of disagreement between Baron Zemo and his dad, Baron Zemo. Helmut wants to keep Captain America alive so he can suffer, whereas Heinrich thinks this and Helmut are stupid and it's a far better idea to just shoot Steve dead ''now''.

** Poison Ivy fouls up in her [[Recap/BatmanTheAnimatedSeriesE5PrettyPoison debut episode]] by slowly taking her time in [[EvilGloating taunting]] and [[TheTease flirting]] with Batman, rather than [[DruggedLipstick kissing]] him the same length she did Harvey Dent earlier, inadvertently ensuring he had enough strength to pull off a PlayingPossum maneuver to escape her [[ManEatingPlant jumbo monster flytrap's]] VineTentacles.

** He attempts to subvert this again in "That Sinking Feeling" by magically tying Link up in chains and immediately preparing to blast him. Lucky for Link, Zelda blasted Ganon with magic before he could do it.

** "Kiss N' Tell": Link (in [[BalefulPolymorph anthropomorphic frog form]]) hits his head on a tree branch while dodging one of Ganon's magic blasts and is knocked out cold. Instead of finishing him off directly, Ganon summons two giant Deeler spiders to do it before taking Zelda to the Underworld without waiting. But when Link wakes up shortly afterwards, his newfound frog instincts unexpectedly take over and he eats them, much to his disgust.

* ''WesternAnimation/TheLegendOfZelda'': Ganon has both played this trope straight and subverted it more than once:

* ''WesternAnimation/TeenTitans'':

* In the ''WesternAnimation/MegaMan'' cartoon, Dr. Wily and his Robot Masters have several moments where he could easily have destroyed Mega Man and/or his friends, but fails due to opting for an excessively elaborate plan:

'''Señor Senior Sr:''' Tradition!

* ''WesternAnimation/TheVentureBros'' features Red Death leaving rival supervillain Blind Rage ChainedToARailway, while explicitly lecturing him about how part of what he likes about that particular killing method is that [[HopeSpot it leaves a small possibility of escape]], meaning that the person will spend the whole time struggling rather than resigning themselves to their fate. However, in this case, it's rather thoroughly justified, as Red Death's motivation isn't to kill Blind Rage (who is no real threat to him), but rather to send a message to his bosses--something that [[MortonsFork can be accomplished equally well]] by Blind Rage reporting back scared shitless or Blind Rage's corpse being splattered across the tracks.

** In one episode, Slade blackmails Robin into being his apprentice by infecting the other Titans with nanomachines that can kill them literally with a push of a button. Robin gets around this by infecting HIMSELF with the nanomachines, thus giving Slade the choice between killing all the Titans thus removing them as a threat but losing Robin as his apprentice, or potentially getting Robin as his apprentice at a later date, but leaving the Titans around to get in the way of his plans. Naturally as per this trope, he does the latter instead of the much more sensible former.

* ''WesternAnimation/BarbieLifeInTheDreamhouse'' has Closet, the AffablyEvil MasterComputer, exhibit this twice. First, he neglects to keep an eye on Barbie, Midge, and Summer while gloating to Ken, allowing the three of them to ditch him through an AirVentPassageway. Later, Closet threatens to fry Barbie and her friends in a giant drier, only to hear the oven's timer go off. In response, he tells the girls not to move, then leaves to check on the crème brulee he's baking. The girls seize the opportunity to remove the Dreamhouse's CPU.