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[[quoteright:350:[[Webcomic/TheOrderOfTheStick http://static.tvtropes.org/pmwiki/pub/images/complexity-addiction_oots_7002.png]]]]
[[caption-width-right:350:Let's hope no one asked for her to repeat that.]]

->''"What's he up to now? It'll be something devious and over-complicated. He'd get dizzy if he tried to walk in a straight line."''
-->-- '''The Rani''' (about the Master), ''Series/DoctorWho'', [[Recap/DoctorWhoS22E3TheMarkOfTheRani "The Mark of the Rani"]]

A character comes up with a ridiculously elaborate plot that is so meticulously planned out that [[TemptingFate it can't possibly fail]]...

But it will. So why didn't they come up with a [[MundaneSolution simpler plan]]?

There's a simple explanation. This character has a Complexity Addiction. They're addicted to coming up with complex schemes, such as the GambitRoulette. They simply can't help but make [[ThereIsNoKillLikeOverKill an overdone, overblown plan]].

Maybe they're insane. Maybe they're bored. Maybe they view it as being [[MadArtist artistic]]. Maybe simple plans [[ItAmusedMe aren't as amusing]] or [[ForTheEvulz as evil]] or are [[VictoryIsBoring just too boring]] for them. Maybe they consider their enemies {{worthy opponent}}s and that only an equally worthy plan should be used to defeat them. Maybe they [[{{Handwave}} don't even know]] the reason. [[RuleOfFunny It's Funny]], or [[RuleOfDrama it's Dramatic]], or [[RuleOfCool it's Cool]]; that's all that matters.

Expect a smarter character to [[StatingTheSimpleSolution point out the existence of a simpler solution]], often something along the lines of "WhyDontYouJustShootHim". These characters frequently suffer from BondVillainStupidity. May overlap with VillainBall.

See also ASimplePlan, where a very simple plan should have worked, but goes horribly awry. Contrast CombatPragmatist. See also DidntSeeThatComing and CuttingTheKnot. Additionally, see RubeGoldbergDevice for machinery built by people with a Complexity Addiction. Compare OvercomplicatedMenuOrder for a similar situation, but with food/drink.



[[folder:Anime and Manga]]
* ''Manga/{{Bleach}}'': Aizen has a bad case of this. During the Soul Society arc, he had a very complicated plan to obtain the MacGuffin. When that (inevitably) failed, he simply walked up and took it. Why he didn't do that in the first place? Addictions are a strong force to be reckoned with. [[spoiler:Later justified as he revealed his goal during that arc wasn't JUST to acquire the Hogyoku (which he'd already known Rukia had), but to set up an extreme training regime to groom Ichigo into a suitable opponent through which he could further strengthen himself.]]
** The Hueco Mundo arc is where he really succumbs to it. Aizen builds up an army of Arrancar, hollowfies Tousen and makes war with Soul Society. While Aizen has an ability that could let him easily defeat the entire Gotei 13, he more or less deliberately gets everyone but Gin killed for no real reason aside from it being more complex than simply single-handedly killing everyone with his overwhelmingly unfair powers personally. More idiotically, the only point the army could have possibly served beyond intimidating Soul Society was to serve as cannon fodder against Squad 0, the only real threat to Aizen's plan at this point. Aizen didn't seem to notice this, and thus made the creation of the Arrancar army ''completely pointless''. [[spoiler:Mostly justified in that the army itself was just a smokescreen to buy time for the Hogyoku, which Aizen thought would make him invincible, to truly awaken, as well as to keep attention away from Wonderweiss, the one actually integral Arrancar that was in truth the specifically-designed trump card against Genryusai Yamamoto. A portion of the army also served as additional training for his envisioned punching bag Ichigo.]]
** When she first used Resurrección, Harribel displayed the necessary speed and power to get around Hitsugaya's defenses with her sword, and could have ended the fight at literally any point. Instead, she spent the entire rest of the fight playing tug of war with her [[MakingASplash water powers]] and his [[AnIcePerson ice powers]], evidently attempting to set up some sort of [[LimitBreak super attack]].
** Zommari had a case that rivaled Aizen's. Instead of just using his body and mind-controlling powers to kill Byakuya and everybody else in minutes, he insisted on toying with him, twisting the knife and explaining every aspect of his powers in tiny, minute detail, giving Byakuya more than enough information and time to overcome them and turn things around. Byakuya even keeps pointing out that he could probably just kill him at any point. Byakuya does sacrifice his arm when Zommari aims his power at the Captain's head, though Byakuya allows him to keep taking control of body parts and slicing the tendons for no apparent reason but being too arrogant to use Bankai until he's out of limbs.
* ''Anime/MazingerZ'': In episode 39 TheDragon Baron Ashura captured TheHero Kouji and [[HumongousMecha Mazinger-Z]] and gave him the "join-us-or-die" choice. After Kouji's predictable answer, [[KangarooCourt Ashura sentenced him to death]], and instead of shooting him, Ashura's {{Mook}}s started a bunch of giant power saws and drills to cut Mazinger-Z to pieces (it must be mentioned that [[BigBad Dr. Hell]] and [[CoDragons Count Brocken]] were waching the scene and Brocken told he would just shoot him).
* In ''Manga/{{Naruto}}'', the entire plot would have been superfluous if [[BigBad Tobi]] were not fond of this trope. His stated goal, [[AssimilationPlot The Moon's Eye Plan]], requires [[GottaCatchThemAll capturing nine]] [[SealedInsideAPersonShapedCan Jinchuriki]]. He could have achieved his goal more or less ''by himself'' in a matter of months, if not sooner, with his own powers: his primary power (involving his Sharingan) makes him intangible, allows warping people into his pocket dimension, and teleporting himself and other wherever he likes, and his ''secondary'' powers (involving Hashirama's cells) give him enough offensive and defensive abilities to overwhelm most characters in the Naruto universe. Instead, he spends 17 years setting up the Akatsuki with much less capable subordinates and then sends ''them'' to capture the said Jinchuriki, and eventually starts a ninja world war to capture the last two Jinchuriki. This is even more jarring because most Jinchuriki are ''hated'' by their villages which meant Tobi was unlikely to face too much opposition if he carried out his plan alone.
** During the Invasion of Konoha arc, Orochimaru has managed to place a kunai to Sarutobi's neck, but rather than kill him right then to win, he chooses to back off, makes a long-winded speech about what it feels to fight against a teacher, and then summons the souls of the previous Hokages (who were Sarutobi's teachers) so that Sarutobi can experience what he just talked about.
* ''Manga/MutekiKanbanMusume'':
** Miki as TheBully and a JerkWithAHeartOfGold, displays this when at episode 3A when she insists on fighting the WorthyOpponent when she could easily avoid it. And at episode 5 B, she insists of beating Ohta to use him as a stepping stone to escape a well, when Ohta had a rope and Miki could’ve just let him rescue her, she simply handwaves it.
** Kankuro's plans to defeat Miki always had to involve some kind of duel.
* [[http://digimon.firstagent.net/2013/04/frontier-episode-29-darkness-before-dawn.html This]] blog argues that this was Mercurymon's FatalFlaw in ''Anime/DigimonFrontier'', stating that ultimately his plans were "all too cute, more focused on the spectacle of his victory than seeking out the most certain path to it".
* ''Anime/TransformersSuperGodMasterforce'': In a HenshinHero series, Hydra chooses that rather than attacking his enemies while they're regular, vulnerable humans, he'll instead create overly-elaborate scenarios (pretending to be a photographer and kidnapping Lightfoot's father; pretending to be a film director, hiring a film crew, setting up a shot in the middle of a desert and convincing Ginrai to take part) before attacking his foes, or tag-teaming them with his brother, which actually worked the first time they did it (until he decided to just up and leave). But the absolute worst example he came up with was in episode 21, where he decides to kidnap every single doctor in the world, which would apparently cause everyone to realise how fragile they were, and make the entire human race loose the will to live.
* ''Manga/PokemonSpecial:'' Mask Of Ice, the BigBad of the Gold, Silver and Crystal arc, lives and breaths this one. He wants to capture a Celebi, which only shows up at a specific time at the Illex Forest Shrine, and can only be caught by the GS Ball, which can only be made with feathers taken from Ho-Oh and Lugia. Apparently just soliciting the help of a trainer or an expert, like Professor Oak, never occurred to him, since he sets out on a ridiculously circuitous plan that involves kidnapping children, levelling Ecruteak, imprisoning the Legendary Beasts, attacking places all across Johto, and antagonising the Gym Leaders of Kanto and Johto.
* In ''Anime/KingsglaiveFinalFantasyXV'' The Empire's entire invasion plan in a nutshell. First, they offered a peace treaty. 2nd [[spoiler:they kidnapped Lunafeya]]. 3rd, [[spoiler:lure her bodyguard there, kill the bodyguard, and leave bodyguard's body in the dump]]. 4th, [[spoiler:hoping the body will be discovered before the invason]]. 5th, [[spoiler:Hoping someone make a connection as weirdness of her dying place is not her assigned mission place]]. Then [[spoiler:predicting the Kingsglaives will rescue Lunafreya will know where to look]]. Then [[spoiler:place Daemons in the fleets' cargo]]. Then [[spoiler:make sure subverted Kingsglaive members to be included in rescue attempt]]. Then place their emperor, acting chancellor, and empire's most competent and senior ruling members in the heart of enemy capital, now with renewed hostility. Finally, start the invasion and plan of stealing crystal. Seeing Emperor Aldercapt and Izunia are back to their homes safely is very dumb luck at their part as step number 4 and 5 work at all. They should have invaded right away as now their words are less trustworthy then before as they broke their promise of peace.

[[folder:Comic Books]]
* ''Franchise/{{Batman}}'' villains have this like it's contagious.
** Justified for ComicBook/TheJoker, who creates these elaborate plots to see if they'll ever kill his nemesis, but they never work. He wants to kill his enemy with a '''bang''', not a simple gunshot (even though he ''has'' resorted to a gun before).
** Harley Quinn once even asked him outright, "WhyDontYouJustShootHim"
** ComicBook/TheRiddler, despite "going straight" for a while, [[StatusQuoIsGod eventually got back into the habit]]. The Cluemaster, on the other hand, managed to kick the clue-leaving compulsion, and became a (comparatively) more cunning villain. Riddler tried to do normal crimes at one point, but was caught because he was leaving riddles... that he never actually intended to leave and was terrified after discovering he'd left. This convinced him he was actually mentally ill and needed professional help. This is something of a FatalFlaw for old Eddie - if he just went for straightforward criminal plots, he'd be pretty successful, but his obsession is not with gaining wealth but with decisively outdoing Batman, and what better way to prove you're better than winning with a handicap?
* When the entire ''Franchise/SpiderMan'' [[ComicBook/TheCloneSaga Clone Saga]] in all of its insane permutations was ''finally'' revealed to [[RetCon have been]] masterminded by ComicBook/NormanOsborn (who had been faking his own death for years, to boot), for the simple purpose of ''driving Peter nuts.''
* ''Comicbook/{{Supergirl}}'':
** Super-villain Black Flame has a serious trouble with this. In ''Adventure Comics #400'', Supergirl is at her mercy: trapped in a locked room, unconscious and sprinkled with Green Kryptonite. And Black Flame orders her hired guns to hurry up and bring Supergirl to a DeathTrap before the Kryptonite kills her because she doesn't "want her go that easily". Supergirl survives Black Flame's elaborate death trap but she is immobilized and rendered unconscious. So Black Flame kills her? Nope. She sets another death trap up and waits for Supergirl coming around.
** In ''[[Comicbook/{{Supergirl 1982}} Supergirl Volume 2]]'' #20, Parasite manages to knock Supergirl out. Instead of killing her right away, he puts her in a complex death trap.
* Franchise/{{Superman}}:
** In ''Superman's Pal ComicBook/JimmyOlsen'' #30, Superman adopts Jimmy as his son for a 30-day trial. During this period, they visit the Fortress of Solitude, where Superman shows Jimmy his mural of a solar system he created, in which the inhabitants named various parts after him (such as "Superman's asteroid", "Superman's planet", ect.). After that, Superman leaves Jimmy be while he checks his "electronic oracle". The oracle predicts that on the day the trial adoption expires, "Superman will destroy his own son!" Now, Superman has two options: A) tell Jimmy the bad news and revoke the adoption to protect him, or B) consider that the oracle has problems with homonyms and conclude that it may be referring to the sun in the aforementioned solar system. What Superman decides on is option C) resort to {{Superdickery}} and treat Jimmy like crap without explaining why until Jimmy backs out of the trial.
** UsefulNotes/{{The Silver Age|of Comic Books}} Franchise/{{Superman}} had a severe ComplexityAddiction. Thus, he was always setting up elaborate hoaxes involving robot duplicates, fake newspaper headlines, and Batman wearing a Clark Kent mask, all to trick the aliens secretly preparing to attack Earth.
* [[ComicBook/{{Daredevil}} Bullseye]] could probably kill people just fine with a regular gun, but he prefers to use different kinds of items with his incredible aiming skills. When he was posing as Hawkeye in ''ComicBook/DarkAvengers'', he wasn't too happy with Norman Osborn limiting him to only using a bow and arrow. A mini-series starring Bullseye goes into detail about this. He was ecstatic when he finally killed ComicBook/{{Elektra}} and is ''constantly'' looking for a way to get the same rush, with no success. He keeps on taking assignments harder and more impossible than the last simply for the thrill of it.
* Every protagonist Jim Starlin has written in the Creator/MarvelComics pre-ComicBook/{{Annihilation}} cosmic narrative, whether they were ComicBook/{{Thanos}}, Adam Warlock, the Magus or the Goddess, used incredibly byzantine plans, often with a relatively mundane goal in mind (in ''ComicBook/TheInfinityGauntlet'', for example, Warlock's strategy was aimed at getting Thanos to raise his hand at a specific moment so the ComicBook/SilverSurfer could attempt to snatch the Gauntlet from him). The justification is that these characters are all contending with opponents who are master planners themselves and often possess some kind of super-ESP which would alert them to any simple scheme.
* In ''ComicBook/TheAvengers'' #169, multimillionaire Jason Beere learns he is dying, and out of ItsAllAboutMe decides the rest of the world should die with him. He comes up with a plan involving about sixteen individual steps, including wiring a world-destroying NeutronBomb to his failing heart, donning power armor to attack the Avengers, and planting fake bomb plans to have them go on wild goose chases around the world to assemble a taunting message. The plan fails somewhere around step ten when Iron Man puts him in Tony Stark's old life support chest unit. Beere could have accomplished his goal with a two-step plan: 1) acquire world-destroying bomb, 2) detonate bomb.
* Doctor Doom from ''ComicBook/FantasticFour'' is notorious for this. To the extent that more often than not it seems as if any given scheme was carried out by somebody that was ActuallyADoombot and Doom himself almost appears to be in multiple places at the same time. Generally this does little to improve the overall results of his many conspiracies beyond giving the heroes (and sometimes other villains) a good workout.

[[folder:Comic Strips]]
* ''ComicStrip/CalvinAndHobbes'': As members of the secret club "G.R.O.S.S." ('''G'''et '''R'''id '''O'''f '''S'''limy Girl'''S'''), Calvin and Hobbes often come up with schemes to annoy and/or terrorize their neighbor Susie. [[http://www.gocomics.com/calvinandhobbes/1993/08/05 One day]], Calvin devises a scheme that involves writing a message in code which Susie will believe was written by Calvin for Hobbes, and "accidentally" letting Susie discover and read the note, which says that Calvin doesn't want Susie to go behind their house at noon. Calvin thinks this will naturally draw her to the back of his house at noon, at which point he and Hobbes can hit her with water balloons. Hobbes asks why they don't just hit her with water balloons right where she's sitting now. Calvin replies, "You're a good officer, Hobbes. But let's face it, you don't have an executive mind." Hobbes still thinks his idea sort of makes sense.
* The original appearance of the RubeGoldbergDevice was in newspaper comics, in which a hugely complicated and often ridiculous device was built to accomplish some mundane function, e.g., ringing a doorbell by having a button release a cat that chases a mouse along a track, which generates a breeze which pushes on a series of fans which rings the bell.
* Jason of ''ComicStrip/FoxTrot'' may be a genius but he tends to go for the massively complex ideas rather than simple ones. He spends hours vainly trying to get past a monstrous creature in a computer game, dying each time no matter what offense he tries. Paige ends up passing the level [[SheatheYourSword by just walking right by the guy]].
-->'''Jason:''' Look at him! He's huge! He's strong! He's sitting on a pile of skulls! How are you not supposed to fight him?\\
'''Paige:''' What is your IQ again?

[[folder:Fan Works]]
* In ''ComicBook/PowerGirl'' fanfic ''Fanfic/AForceOfFour'', [[WarGod Mars]] wants Franchise/WonderWoman, her daughter and [[ComicBook/PowerGirl their ally]] dead. So that he builds a coliseum and forces them into a gladiatorial battle with his own champions instead of merely blasting them into oblivion.
* Lampshaded in ''Fanfic/CalvinAndHobbesTheSeries'':
-->'''Andy:''' Say, Calvin, is there any reason [[WhyDontYouJustShootHim why they didn't just shoot you dead with their ray guns, right then and there]] and save the trouble of thinking up of another elaborate plan that's sure to fail?\\
'''Calvin:''' Rupert always wants stuff to be complicated.
* ''Fanfic/HarryPotterAndTheMethodsOfRationality'':
** Makes a cameo appearance, ''in actual drug form''. Called [[IdiotBall Bahl's Stupifecation]], it is a narcotic that has the side effect of bringing about idiotically complex and impractical plans in Dark Wizards with Slytherin tendencies. The example presented in the narration is [[TakeThat suspiciously similar]] to Voldemort's plan from ''Literature/HarryPotterAndTheGobletOfFire''.
** Lucius Malfoy warns his son that any plan that requires more than three things to happen will never work; however, since only an idiot makes things as complicated as possible, the real limit is two. This lecture he did as a TakeThat to an InUniverse {{Expy}} of ''Anime/DeathNote'', because he noticed that Draco wanted to borrow inspiration from it for his rivalry with Harry.
** Voldemort seems to have a bad case of this, with many bizarre plots similar to the ones in canon. Harry has difficulty understanding how someone so stupid could be an actual threat. [[spoiler:This is because Voldemort was a ''game'' to Tom Riddle, just practice for the real villain he planned to play later]]. He tells Harry that while essential plans should be simple and perfect (eg; apparate in front of your target and hit them with the Killing Curse), nonessential plans can be as complicated as you want, since by definition they're not important. This has the side benefit of giving you a reputation for [[ObfuscatingStupidity succeeding through blind luck rather than skill]].
** In the same story Dumbledore has a reputation for not only using incredibly convoluted plots, but for also launching fake plots with no actual goals. The reason behind this is [[spoiler: he's actually deliberately triggering either-or prophecies and rarely understands the actual string of events himself, so he made sure they weren't out of character.]]
* Lucius Malfoy in ''Fanfic/ChildOfTheStorm''. While he isn't defeated through any misstep of his own, it is noted as the defining trait of the Malfoy house, and often trips them up when doing something simple would be much more effective.
** Arguably [[Creator/NimbusLlewelyn the author]]. There is a ''reason'' that this [[MassiveMultiplayerCrossover fic]] has the single longest entry on the GambitPileup page, and the above could be a tacit acknowledgement of this by him.
* The NeglectfulPrecursors in ''[[FanFic/SovereignGFCOrigins Origins]]'', a ''Franchise/MassEffect''[=/=]''Franchise/StarWars''[=/=]''VideoGame/{{Borderlands}}''[[spoiler:[=/=]''[=Halo=]'']] MassiveMultiplayerCrossover pretty much brought the events of the three galaxies featured about through this trope combined with [[DuelingMessiahs internal religious conflicts]]. More details can be found on the NeglectfulPrecursors page.
* ''FanFic/RosarioVampireBrightestDarkness Act I'': During the first few chapters, Apoch and Astreal go through elaborate schemes to test the group's power, and ultimately brainwash Rason and Dark, in order to be free of their master Ghaldin; the brainwashing attempt backfires when the sisters' inexperience with brainwashing spells allows Ghaldin to take control of all four of them. When all is said and done and Ghaldin is killed by Inner Moka, Tsukune flat-out tells the sisters that [[CouldHaveAvoidedThisPlot he and his friends would have helped them willingly from the start if they had simply]] ''[[CouldHaveAvoidedThisPlot asked]]''.
* ''FanFic/TheRiseOfDarthVulcan'': The Princesses eventually realize, with the aid of Diamond Tiara (who spent time as his prisoner) that this is a defining trait of the titular VillainProtagonist. It's not enough for him to simply carry out a plan and beat his enemies -- he has to do it in such a way that his enemies are made to look like utter idiots compared to him, in order to justify his opinion of them.
* In ''[[http://cartoon.adult-fanfiction.org/story.php?no=600095039 How I Learned to Love the Wild Horse]]'', Brittany informs [[WesternAnimation/TotallySpies WOOHP]] of the [[Manga/RanmaOneHalf Nerima Wrecking Crew]] and cites that she believes them to be a terrorist organization with Ranma as their leader. Ranma has recently moved to Beverly Hills and enrolled in the same school as the girls, so Jerry has them put him under surveillance to learn his motives for coming to America. It's later revealed that Brittany was helping Ranma get away from Nerima and he was going to be hired as a martial arts instructor for [=WOOHP=] but the organization doesn't usually do bodyguard details so she instead told them he was a terrorist leader. Why she couldn't tell the truth and ask for an exception is never explained.
* In ''Series/BuffyTheVampireSlayer''/''ComicBook/{{Supergirl}}'' story ''Fanfic/TheVampireOfSteel'', Buffy and Supergirl have been captured by a mob of vampires. Yet [[BigBad Vladislav]] doesn't still want to kill them because he needs a sacrifice to open a portal and summon some kind of Lovecraftian horror. When one of his underlyings is about to just shoot them, Vladislav goes mad.
-->“All I want to know is what this setup is all about,” said Supergirl. “If we’re going to be the main course for this vampire or whatever you’re going to be hosting, just call me curious.”\\
“Call you dead,” said the guy with the bucket, and drew a .38.\\
Vladislav slapped his hand, then slapped his face. “How many times do I got to tell you? How many times? How many?”\\
“No more, boss, no more,” pleaded the vamp. “I understand. I understand. I swear on my father’s coffin.”\\
The fangfather buried his hands in his underling’s turtleneck. “I don’t really have time for this aggravation, Lester. You got me?”\\
“Gotcha, boss.”\\
“I said we don’t shoot the women, and we don’t shoot the women. We need them for later. Got that?”
* A variant occurs in ''FanFic/TheRWBYLoops''; Ozpin is stated to be addicted to ''conspiracy''. This generally results in keeping secrets past a point where it would be useful and revealing things via convoluted methods or only after being confronted directly. Most of the other loopers find this habit annoying and frustrating.
* Half the cast in ''FanFic/TheRealUs''. There is a complicated list of what the Weasleys are and aren't allowed to know (for example, they can know that Sirius is a good guy, but must believe Snape is going to betray them). And Harry would rather set up a complicated network of spells (or at least, have the school staff do it for him) than not take his secret girlfriend to the Yule Ball.
* ''FanFic/ProfessorArc'': Cinder Fall, [[TheChessmaster a woman who spends her all her time scheming]], assumes that Jaune has his own brilliant plan to serve his own ends, and in vain tries to figure it out. Not that he's simply at some kid [[IndyPloy blundering and bluffing his way out of trouble]]. Jaune more or less goes along with this, because [[YouHaveOutlivedYourUsefulness he knows what would happen if Cinder saw him as not worth her time]].

[[folder:Films -- Animation]]
* Yzma from the ''Disney/TheEmperorsNewGroove'' (and the SpinOff series ''WesternAnimation/TheEmperorsNewSchool'') has an affinity for making complex plans to destroy Kuzco, which never work. Kronk [[LampshadeHanging lampshades]] this at least once.
-->'''Yzma:''' How shall I do it? [[http://www.youtube.com/watch?v=5Cx7jzq2Bx4 Ooh, I know]]. I'll turn him into a flea, [[BalefulPolymorph a harmless little flea]]. And then I'll put that flea in a box, and then I'll put that box inside of another box, and then I'll mail that box to myself. And when it arrives, [[EvilLaugh AH HA HA HA]], ''[[DropTheHammer I'LL SMASH IT WITH A HAMMER]]!''
** She does decide against the above plan in favor of [[WhyDontYouJustShootHim poisoning Kuzco]]... [[SkewedPriorities in order to save on postage]].
* In the theatrical ''WesternAnimation/RecessSchoolsOut'' film, the MadScientist Dr. Philium Benedict builds a tractor beam in order to move the moon. His {{evil plan}} goes something like this:
##Use a tractor beam to move the moon.
##This will change the seasons, making it winter all year long.
##With summer gone, schools will eliminate summer vacation.
##Children will spend more time in class, becoming better-testing students.
##People will be so grateful to him, they will elect him President of the United States.
** Ignoring the fact that the whole thing is just a really roundabout way of getting into the highest political office in the country, [[InsaneTrollLogic there are just so many things wrong with that plan that it warps past funny and goes into tragic]]. The first step alone would have [[InferredHolocaust catastrophic consequences]]. TJ flat out tells Benedict that removing summer won't remove summer vacation, but Benedict just replies, "I can try."

[[folder:Films -- Live-Action]]
* In the Tim Conway/Don Knotts movie ''Film/ThePrivateEyes'', a witness to the Morley murder calls the title characters to Morley Manor, then arranges for every single person in the Manor other than the killer to appear to be murdered, in order to trick the murderer into confessing in front of two police officers. Why he couldn't just go to the police and ''tell'' them who the murderer was never brought up. [[spoiler: Then again, Lord Morley never could get ''anything'' right.]]
* ''Film/AustinPowers'' spoofs this trope as it commonly appears in spy films. [[BigBad Dr. Evil]] is notorious for making his plans to kill the titular character exceedingly complicated, such as in the first movie where he has Austin and Vanessa standing on a platform suspended over a pool of water with mutated, enraged sea bass ready to eat them, in a secluded room with the door closed and one easily defeated guard stationed there. Dr. Evil's son, Scott, is [[LampshadeHanging usually the one who calls him out]] on these things and [[StatingTheSimpleSolution states much easier ways]] to kill Austin. Earlier in the film, Number Two kept trying to convince Dr. Evil that their best option was to CutLexLuthorACheck, [[CardCarryingVillain which Dr. Evil roundly objected to]].
** In the second film, Dr Evil uses a time machine to steal Austin's mojo (rendering him impotent) rather than (as Scott suggests) simply shooting Austin at a time they know Austin will be occupied. Furthermore, when Dr Evil has Austin at his mercy, he has him and his partner Felicity placed in a room with slowly retracting floors over a pit of lava. Much like the first film, one inept guard is stationed there.
** In the third film, Goldmember has Austin's father Nigel at his mercy, but much like Dr Evil, he fails to kill Nigel outright. Instead, he leaves him to die on a smelter. As is typical, the plan fails.
* In ''Film/TheBourneIdentity'', Jason Bourne needs to get some information from a hotel receptionist, but he's afraid that the police will come after him or his girlfriend the moment any of them step inside. Therefore he comes up with a complicated plan of action, involving her entering, counting the number of steps she takes from the entrance, counting how many civilians, guards, etc. there are, and him then calling her via the lobby phone to plan further ahead. This is explained via Jason's voice-over as we see her doing this. As she looks at the telephone, the camera cuts to Jason outside, dialing the number. No answer. He hangs up in a hurry and prepares to go in, only to find her standing right behind him with the papers in hand.
-->'''Jason:''' You just ''asked'' for it?
* Present in ''Film/CaptainAmericaTheWinterSoldier'' with the [[spoiler:HYDRA]] plan to assassinate [[spoiler:ComicBook/NickFury]]. [[ComicBook/BuckyBarnes The Winter Soldier]] has a weapon capable of destroying the armored car, yet the plan consists of first attacking him with a posse of fake policemen and a battering ram before hoping the car will drive down a random street where the Winter Soldier is waiting for him. Subverted later when they actually do just shoot him.
* ''Film/AvengersAgeOfUltron'' both plays it straight and subverts it.
** ComicBook/ScarletWitch shows shades of this as she and her brother ComicBook/{{Quicksilver}}'s primary motivation for joining up with ComicBook/{{Ultron}} is revenge on [[ComicBook/IronMan Tony Stark]] for [[spoiler:creating the bombs that destroyed their home and killed their parents when they were children]]. However, she passes up an opportunity to kill him in the ''first 15 minutes of the film'' when she manages to catch him out of his armor and enthrall him with her PsychicPowers. At that point they could have just snapped his neck or something ([[WhyDontYouJustShootHim which Quicksilver]] [[LampshadeHanging lampshades]]) but instead she chooses to let him take Loki's Scepter and leave, hoping it will corrupt and destroy him and the other Avengers. This is despite the fact that she already has as good a chance to kill Tony as she's ever going to get, and her vendetta is with him personally, not the Avengers as a whole.
** On the other hand Ultron earns the distinction of being the first major villain in the MCU who tries to use the most [[MundaneSolution simple, effective and straightforward solution]] first ([[spoiler:stealing the nuclear codes and using the nukes to destroy humanity]]) and only resorts to the more "colorful" overly complicated methods because that plan keeps getting thwarted.
* The comedy ''Film/WithoutAClue'' imagines that Watson is the true genius and Sherlock Holmes just an actor hired for good publicity. A kidnap victim leaves behind a mysterious set of numbers and both Watson and Holmes spend hours going through a variety of obscure clues, jumps in logic and more to finally figure out that the victim is leaving behind a roundabout way of finding his location. When he's finally rescued, the victim is happy they saw the numbers...which were simply the address of the theater he was being held prisoner in.
* This is Schultz's fatal flaw in ''Film/DjangoUnchained''. Schultz develops this crazy plan to have him and Django impersonate slave traders looking to buy a slave prize-fighter, and get Django's wife Broomhilda thrown into the bargain. Then Candie, the guy they're dealing with, figures it out thanks to his HypercompetentSidekick, and forces them to pay the exorbitant full amount for just Broomhilda at gunpoint, telling them point-blank that he would've sold her to them for cheap if they'd come to him honest. [[spoiler:Finally, after Candie [[SmugSnake keeps rubbing his victory in Schultz's face]], Schultz can't take it anymore and shoots Candie point-blank. Naturally, Candie's guards blow Schultz away.]]
* The Film/JamesBond villains are bad enough [[BondVillainStupidity to name a whole separate trope]] -- for instance, instead of simply killing Bond they [[Film/DrNo beat him up and leave him in a somewhat easily escapable cell]], [[Film/LiveAndLetDie leave him in the middle of an alligator farm]], and [[BlofeldPloy shoot a mook that failed them instead]].
* ''Franchise/StarWars'':
** Heroic example in ''[[Film/ThePhantomMenace Star Wars Episode I: The Phantom Menace]]'': Qui-Gon's ridiculously complicated plan to get the hyperdrive replacement needed to repair Amidala's ship from Watto. Watto is apparently the only vendor in Mos Espa who has the part they need, but he won't take Qui-Gon's Republic credits because they're worthless on Tatooine. So Qui-Gon hatches an elaborate plan involving tricking Watto into gambling the part in an upcoming Pod Race and then entering Watto's nine-year-old slave Anakin into the race and having him win it for him. Even though the movie makes it pretty clear Qui-Gon's Force powers meant he knew Anakin would win, you'd think there might have been and easier (and less dangerous) way. Like finding someone willing to exchange credits for a local currency, or trading their current ship for a less valuable but functional one. Or just book passage on a transport, or [[Film/ANewHope with a smuggler]] or something. Give them all the money he has now (a trader or a smuggler would have use for Republic credits, unlike a planet-bound merchant like Watto), and promise them a reward from the Jedi council when they arrive at Coruscant.[[note]]Funnily enough, this is pretty much exactly what his former student Obi-Wan does about two decades later to get off the same planet. And if it hadn't been for the Empire destroying Alderaan, it would have worked just fine.[[/note]]
** Emperor Palpatine in ''Film/ReturnOfTheJedi'' develops a frankly ridiculous plan due to SkewedPriorities, leaking schematics of the Death Star II and putting himself personally at risk in order to trap the Rebels and methodically destroy them with the Death Star II. This is highlighted by the fact that, per Vader, Imperial Intelligence ''knew where the Rebels were assembling their fleet''. A strike right then and there by a couple dozen battle squadrons from the local sector fleet could have crippled the Rebellion. But [[JustifiedTrope Palpy was more interested in seducing Luke to the Dark Side than in winning a military victory]], and kept pursuing his overcomplicated plan even after it became apparent the Rebels were not playing ball. {{Lampshaded}} in the spin-off novel ''Literature/ShadowsOfTheEmpire'' Darth Vader thinks Palpatine's EvilPlan is outright ''stupid'' (though naturally, he keeps it to himself).
** The plan to rescue Han from Jabba the Hutt at the beginning of ''Jedi'' is also ridiculously complex, to the point where there is still considerable debate among fans as to what the original plan was, and how much was planned and how much was improvised, or if there were possibly several different plans going on at once. First Lando infiltrates the palace as a guard, then Luke sends the droids to Jabba as a "gift", then Leia arrives disguised as a bounty hunter with Chewie as her prisoner, then Leia frees Han from the carbonite but is discovered and taken captive, then Luke arrives and attempts to negotiate only to be forced to fight the rancor, then Jabba gets mad and sentences everyone to death, then they're taken to the Sarlacc Pit, then they kill everyone and go home. One wonders why any step besides that last one was necessary. Luke does seem to want to give Jabba the opportunity to resolve things peacefully, but that still makes everything that happened before Luke arrived pointless.
* In ''Film/NowYouSeeMe'', the Four Horsemen's plans are insanely overcomplicated, given the simplicity of their true goals. This is part of the idea, though; the motive wasn't just simple robbery, but to make sure the ones being robbed knew who did it and couldn't prove how.
* The villains from ''Film/JackReacher'', who explain it as "We make it messy now so it won't be messy later." [[spoiler:To explain, they overcomplicate their plan to do SerialKillingsSpecificTarget with a sniper and letting an ex-Marine with a prior history of killing sprees take the fall by 1) leaving behind an OrgyOfEvidence, 2) have their DetectiveMole find every single clue they left behind and thus accelerate the investigation and make it iron-clad (and thus have Reacher question why such absurd thoroughness), 3) use a sniping spot that would leave behind lots of evidence, when they knew that their FallGuy was ex-military and would ''not'' have used it, 3) attempt to strong-arm and kill anybody who asks too many questions even if the questions probably won't lead anywhere if they just lay low]]. All of this together leads to Reacher to find out that it was a set-up, and when they come gunning for ''him'', a RoaringRampageOfRevenge ensues.
* Mafia hitwoman Salino of ''Film/TheSting'' is pretty much this trope ([[InformedAbility even though she's supposed to be Lonnegan's top assassin]] and his immediate choice to send after Hooker when he escapes his regular Mooks a second time, even if his advisor thinks it's overkill). She goes to Chicago, becomes a waitress, pretty much waits for Hooker to come to her instead of looking for him, waits a long time to act (much longer than it would considerably take to confirm that it's him), becoming an apparent LoveInterest...and, on the day of the titular "sting", she gets shot by a gunman hired to protect Hooker before she can draw the silenced gun on her purse.
* The villains in Nolan's ''Film/TheDarkKnightSaga'' tend to exhibit this. The Joker definitely wins though, every step of his plan involves incredibly complicated plans and reliance on things he can't possibly know. He somehow knows exactly how much time it will take Batman to [[spoiler: save Harvey Dent and that the police will be too slow to save Rachel.]] If Batman was a minute slower or the police had a car in the area then the Joker's "ace in the hole" wouldn't exist anymore.
* Mr. Freeze in ''Film/BatmanAndRobin'' steals several massive (roughly the size of a fist) diamonds to power a freeze-ray that he then takes to the local observatory so as to freeze all of Gotham in order to ransom the city to fund his research for a cure to Mac Gregor's Syndrome. [[CutLexLuthorACheck Why he doesn't fence the diamonds, or patent his cure to Stage One Mac Gregor Syndrome, or even sell his freeze ray to fund his research]] is never explained.
* This is the Dude and Walter's major mistake in ''Film/TheBigLebowski''. They keep assuming that there ''has'' to be some big conspiracy/mystery to explain all these odd events and clues they're encountering, when in reality [[spoiler:there's totally normal and sensible explanations for all of them. The toe, the creepy Nihilists, Jackie Treehorn, Bunny's disappearance, the mysterious car following the Dude, the essay... they're all just random events with simple, non-criminal causes. The only mystery to be uncovered is a minor scam the Big Lebowski is running to bilk some money out of his own charity, and there's nothing for the Dude and Walter do about that other than tell Maude.]]
** Walter [[DiscussedTrope deliberately tries to avoid this]] during the "handoff" scene, preferring to beat Bunny's location out of her kidnappers instead of paying them the demanded ransom. Turns out [[spoiler: there is no handoff. The kidnappers want them to simply drop the money off. Walter doesn't take the news well.]]
* Professor Fate from ''Film/TheGreatRace'' spends the entire race cheating and his reaction at the end of the movie (when the protagonist throws the titular Great Race in order to win over his love interest) is to celebrate the victory for a moment, then lapse into a huge tantrum because, even though he wanted to win, he wanted it on his terms (i.e, by cheating like he was being paid for it). He even goes so far as to scream "YOU CHEATED!" in the hero's ''face'' during all this.
* ''Film/InsideMan'': One of the running plotlines is the police trying to find out what the bank robbers want, since their plan is so confusing and convoluted that it's impossible to tell. This turns out to be the point; [[spoiler:by confusing everyone, they were able to slip out among the hostages after stealing something that wasn't supposed to exist]]. That being said, they still overcomplicated things a bit. They wanted to make money and [[spoiler:expose a war criminal who collaborated with the Nazis]]. They could have done either one easily, but doing both at the same time required the complex plan.
-->'''Russel:''' I'm no saint. I did it for the money. But what's the point of having money if you can't look yourself in the mirror?
* ''Film/JourneyIntoFear'': The Nazis, Muller and Banat. They concoct an elaborate stylish murder plot involving a stage magic show, rather than just dragging Graham into an alley and shooting him; then they go to all the trouble of smuggling him off the boat rather than, say, whacking him over the head and chucking him overboard.
* ''Film/TheNiceGuys'': The plan Amelia developed to expose her mother's corruption (and thus her connection to the Detroit automobile business and ''its'' anti-environmental corruption) is so absurd that the protagonists have a pretty hard time wrapping their heads around it when first explained to them: create a PornWithPlot and have the "plot" be a tell-all expose on said corruption (she explains that the film's producer told her that the fact AllMenArePerverts will ensure nation-wide distribution and thus a large audience... she's told back by the heroes that this exact same fact may mean they won't ''care'' about the message, but she dismisses it). The fact that things get more complex when the porn film's star blabs everything regarding the movie's production on a trip to Detroit, which ends up being overheard by the car manufacturers and they decide to LeaveNoWitnesses (which means that the plan needs to be switched from attempting to get the film picked up and distributed country-wide (yeah, they had nobody waiting in line to do it -- this leaves an untold amount of people dead, by the way) to airing it on an automobile convention (which concludes in a destructive gun battle, and people were visibly dismissing it as a prank before said battle erupted)) doesn't helps ''anybody''.
* ''The Osterman Weekend'' (1983). A CIA agent finds that his own organisation is behind the murder of his wife, so his plan of revenge involves: create a phony Soviet spy network called Omega, faking evidence that will convince a TV producer known to be critical of the CIA that his friends are members of Omega, wiring up his home with video equipment to gather evidence for this non-existent conspiracy, staging an attempted kidnapping of the producer's wife and son so they'll be brought to the house for their protection, {{Mind Screw}}ing everyone so they start to turn on each other, trying to kill the producer (whom he needs for his EvilPlan) and murdering his friends, kidnapping his wife and son for real so he can force the producer to confront the head of the CIA in a live interview about the murder of his wife. Why he never just went to the producer with his accusations, or just kidnapped his wife and son from the outset, is unexplained.
* ''Film/AceVentura'': Ray Finkle's scheme to get back at the Dolphins and Ray Marino in specific for putting the laces on the ball facing the wrong way and making him the laughingstock of Super Bowl history. You would think that a man literally driven ragingly insane would just shoot Marino or something equally simple. Instead, Finkle spends a long time building a fake identity, infiltrating the Miami police and escalating ranks until he becomes the MoleInCharge of the investigation that will ensue from his crimes and getting the resources for both the theft of the Dolphins' mascot Snowflake and the kidnapping of Marino [[spoiler:and this is without counting the whole thing about getting a sex change.]]


%% Please no arguments here.
* ''Literature/HarryPotter'':
** Voldemort's biggest flaw (besides underestimating ThePowerOfLove) is wanting everything he does to be as epic as possible, regardless of practicality. Several characters {{lampshade|Hanging}} this weakness.
*** In ''[[Literature/HarryPotterAndTheGobletOfFire Goblet of Fire]]'', Voldemort sends a [[TheMole Mole]] to Hogwarts to kidnap Harry so as to use his blood in Voldemort's resurrection ritual. They do this by taking a full year to build the mole's false identity, force Harry to participate in the Triwizard Tournament against his will, rig the tournament to let him win, and enchant the trophy to teleport him to the ritual site. The mole apparently does not think to use his trusted position of authority to whack Harry over the head, shove him into his magic chest, and smuggle him out of Hogwarts in the first week of class. Or to make any random object into his office into a Portkey, invite Harry in, and arrange for him to touch it. It's even pointed out that given Voldemort's status as the Evil Overlord of the Wizarding world, he could use ''any random Witch's or Wizard's blood'' for the ritual (it simply requires "blood of the enemy"... who outside of Voldemort's followers is ''not'' his enemy?), but no, Voldemort is obsessed with it being Harry, since he wants Harry's magical protection from his mother's sacrifice in his blood.
*** Harry only survives through books 4 on because the revived Voldemort demands a grandiose and wand-induced death. When Voldemort actually kills Harry in [[Literature/HarryPotterAndTheDeathlyHallows Book 7]], it doesn't stick. Voldemort actually tries to kill Harry as soon as he sees him near the end of [[Literature/HarryPotterAndTheOrderOfThePhoenix Book 5]] when he shows up unexpectedly after Harry had thwarted the Death Eaters' plan. Luckily for Harry, Dumbledore intervenes just in time. When, in Book 6, the Death Eaters actually ''have Harry at their mercy,'' Snape stops them by reminding them that Voldemort wouldn't want somebody else to kill him. Though, admittedly, Snape has other reasons for what he does.
*** Voldemort's ego prevents him from using inconspicuous objects as his [[SoulJar horcruxes]] or storing them in random places, so no one will ever find them. No, he has to, for example, use his grandfather's ring and hide it in his grandfather's shack. So, people who know things about him, such as Dumbledore and Harry, can reason out what the horcruxes are and where to search for them. And these are the objects on which his obsessed-over immortality hinges.
*** One is discovered in [[Literature/HarryPotterAndTheHalfBloodPrince book 6]] to be stored near his childhood orphanage in a cavern that can only be opened with a blood sacrifice, across a lake that can only be safely crossed with a magical boat, at the bottom of a basin full of a torture potion. Since he provides the boat, that particular piece of his soul can be stolen by anyone with a bit of obscure trivia about Voldemort's youth and judicious use of the buddy system -- [[spoiler:or a house elf, which he'd forgotten to ward against]]. Dumbledore is immensely disappointed that Voldemort's grandiosity and sadism overrode his common sense: he made the defenses degrading and horrific at the expense of making them actually lethal.
** In a PlayedForLaughs example, Oliver Wood's various incredibly-elaborate Quidditch play plans, which tend to take multiple magical diagrams to explain.
* This seems to be the generally accepted MO for the Yendi (a cultural group whose [[PlanetOfHats hat]] is being scheming and secretive) in novels set in ''Literature/{{Dragaera}}''. For example, in the novel ''Literature/{{Yendi}}'', the Sorceress in Green arranges for Vlad's rival Laris to try to take over Vlad's territory in an obviously clumsy manner so that Vlad is on his guard when Cawti and Norathar try to kill him so that Vlad's allies in House Dragon will kill Norathar in a way that dishonors them all so that the next Dragon Emperor or Empress will be a person inclined to make the Sorceress's friend Sethra the Younger [[TheDragon Dragon Warlord]]. In the event that the assassination fails (which it does), the deliberate clumsiness of the previous attacks causes Norathar to find out that Laris set her up so that Norathar will kill him in a manner that dishonors her, which would also take her out of the line of succession. This secondary plan also fails.
* A major aspect of the White Court of vampires in ''Literature/TheDresdenFiles'' is that they ''don't'' operate with simple, straightforward plans. In the White Court, approval and influence is based partially on the way one maneuvers against one's opponents, both within the Court and outside of it. A White Court vampire could simply have an enemy gunned down, but that would be met with serious disapproval and a loss of respect and grace, while taking that foe down via ThePlan is viewed with admiration. It's ''institutional'' Complexity Addiction.\\
** Another, equally important reason, is that they work in and around human society far more than many other supernatural beings in the Dresdenverse. Hiring a gunman to shoot your rival can be easily traced back to you. Subtly goading another rival into a conflict with the first so ''he'' hires the gunman insulates you from the consequences far better. White Court culture has grown up around this principle, with the most respected actions being those that "everyone knows" you were responsible for, but nobody can connect you to with any sort of actual evidence. They also apply this to supernatural being stronger than themselves.
* In Creator/PGWodehouse's ''Literature/JeevesAndWooster'' stories, Jeeves has quite a habit of this and it almost never fails, being stuffed with the grey matter.
** In ''Right Ho, Jeeves'' Bertie informs Jeeves that his plan, viz dressing Gussie Fink-Nottle up as the devil and sending him to a fancy dress party to romance a girl, is far too elaborate to ever work. In fact, Gussie forgets the address of the house it's held at and botches the whole thing. Even so this says more about Gussie than about the complexity of the plan.
* Tom Sawyer's plan for freeing Jim in ''Literature/TheAdventuresOfHuckleberryFinn'' might be the UrExample. They could have simply swiped the keys to his shackles and sneaked off in the middle of the night, but Tom insists on sawing the leg off Jim's bed that the shackle is attached to and making a rope ladder just to leave behind as a clue and all manner of other silly things, [[WrongGenreSavvy just because that's how prisoners in the books he's read escape]]. He insists doing it the easy way "just ain't proper." {{Justified}} because [[spoiler:Tom knows full well that Jim was already legally freed in the Widow Douglas' will. [[InnocentBigot He just wants to]] [[RuleOfFun play a fun game]]]].
* In the Miller's tale of ''Literature/TheCanterburyTales'', a young woman and a young man are in love, but the woman is married to an old man. She and the young man, instead of just meeting up during the day in a secluded spot, decide to trick the woman's husband into thinking there's a flood coming, sit on the roof in tin tubs, scare the husband into closing his eyes/passing out for the entire night, then go into the house for a little love-making. Yes, this trope is OlderThanSteam.
* The Assassin's Guild in ''Literature/{{Discworld}}'' simply hates coming across as...''inelegant''. It's part of the job description, after all; a man with a crossbow killing someone for money is just a thug if he doesn't do it with ''class''. This is the reason Sam Vimes is able to foil repeated assassination attempts from the Guild. They always attack him at home or the office, never out in the street ("What, like some common murderer?"), and they always wear full black, which, while cool, is fairly impractical for nighttime stealth (as anyone trained in camo knows, mottled grays or dark greens are better; black just outlines you). Vimes' home and office are riddled with cunning booby traps, and Vimes himself [[CombatPragmatist has no compunctions about fighting dirty]].
* In Creator/SomtowSucharitkul's ''Inquestor'' stories, Inquestors play a very complicated "game" called ''makrugh'' in which the object is mainly to maneuver your opponents--basically, every other Inquestor--into losing face. Since this is pretty subjective, it tends to result in "You lost."/"Oh, but did I?" type conversations.
* In ''Literature/OzmaOfOz'' (And the film adaption ''Film/ReturnToOz''), rather than wipe out the heroes with his unbeatable armies or magic, the Nome King makes them play a guessing game to rescue his victims; players must guess which ornaments are actually transformed people. Run out of guesses and be transformed. The King's steward even points out how stupid this is, especially in that he ''color-coded'' the victims. the Nome King insists that it's more fun this way, and even brags about how he's going to transform the heroes. Ironically, the discussion is overheard by Billina the hen, who uses the information to great effect.
* This is used as a BatmanGambit in the Creator/KimNewman short story "A Shambles in Belgravia", an AlternateHistory where Irene Adler approaches Professor Moriarty to steal some 'intimate' blackmail photographs of herself from the {{Ruritania}}n embassy. Rather than just use a skilled cat burglar, Moriarty stirs up political trouble so there's a demonstration outside the embassy when the time comes to do the theft. It turns out that Irene is working for the head of the Ruritanian secret police who was in danger of losing his job because the country was so peaceful, but Moriarty has now fixed that.
* In the children's series ''The Peterkin Papers'', the Peterkins are all extremely intelligent, even brilliant--but without a lick of common sense. Whenever a problem presents itself with a simple solution and a complex solution, they'll go for the complex one, and the simple one will never even occur to them. Without the common-sense of their neighbor, the Old Lady from Philadelphia, there's no telling how much trouble they'd get into!
* Discussed but averted in Tom Clancy's ''Literature/WithoutRemorse''. When Kelly/Clark comes up with a relatively simple plan to get a special ops team into North Vietnam and the generals and admirals keep wanting to "spice it up", he specifically points out that the more complex the plan, the more things you need to go right, and the more difficult it gets for it to go according to plan. He draws deliberate parallels to the Song Tay raid (which actually happened in real life) and how the plan was almost thuggishly simple yet extremely effective.
* ''Literature/HowTheMarquisGotHisCoatBack'': The Elephant thinks it's a good idea to chain the Marquis to a pole in a room filling with water and ''leave the room''.
* In ''Literature/{{Twilight}}'', the Cullens end up with three (later two) vampires wanting to kill Bella. Instead of simply mobbing the vampires the instant they know of their murderous intentions (Edward knew instantly, as he could read minds) or keeping Bella and her father together and putting her under constant surveillance so they could kill the vampires when they attacked (there were seven Cullens to keep a look out, one of whom could see the future and another of whom could read minds, all against two vampires, since the third defected), they decide to split themselves up so that Esme, Rosalie, Edward, Emmett, and Carlisle go on a wild goose chase after one of the vampires while Alice and Jasper take Bella first to her home in Phoenix [[TooDumbToLive after telling the vamps that want to kill her that that's where she's going]] and then plan to take her to other major cities.
* ''Literature/HushHush'':
** In the first book, [[spoiler:Patch]] has this going on pretty badly as well. [[spoiler:He was stalking Nora for an unspecified amount of time before planning to kill her, which caused him to fall in love with her. Why he didn't just kill her the instant he found her (with his powers and the fact that she's not that smart, it wouldn't have been hard) is never explained]].
** In ''Crescendo'', all [[spoiler:Rixon]] has to do to accomplish his goals is to kill Nora. So naturally he spins it out across the entire book, making her hallucinate her dead father, knocking her out with a drugged card and chasing her through an empty library, trying to drive her off the road, attempting to turn her against Patch, and giving her a bogus spell to have him banished to Hell. The only reason given for him doing this is basically "ItAmusedMe".
* The ''Literature/{{Sharpe}}'' series gives us a heroic (or at least anti-heroic) example: Sharpe several times has his nemesis Obadiah Hakeswill at his mercy, but leaves him to be eaten by tigers, trampled by an elephant, or bitten by poisonous snakes instead of a well-deserved bullet to the head.
* OpportunisticBastard ''par excellence'' Petyr Baelish shows signs of such an addiction in ''Literature/ASongOfIceAndFire'', telling his would-be protégé that he will even make moves that are against his best interests for no other reason than to confuse his enemies as to his true goals. He manages to make this work by never blinking when his plans are thrown into disarray, but adapting smoothly and [[XanatosSpeedChess working up new plans]] to turn the unforeseen circumstances to his advantage. It helps that half of his plans boil down to "sow chaos and then present actual goal as solution to whoever ends up on top so they just hand it to you".
* Prince Nahrmahn of Emerald is a highly intelligent man and one of the best schemers in the ''Literature/{{Safehold}}'' series. While he works for the betterment of his people, he is at least equally motivated by his love of "The Great Game" of international politics. After he makes a HeelFaceTurn, the Empire of Charis turns this trait to its advantage by making him the Empire's chief spymaster, where he gains a reputation as their best analyst.
* The assassins in ''Literature/StateOfFear'' prefer to kill their targets by pressing a live Pacific blue ringed octopus to them, so that they're paralyzed by the octopus's venom.
* In ''Literature/FiftyShadesOfGrey'', Christian seems to have some sort of aversion to simply calling the police about people threatening him. Instead, he sets up needlessly complicated methods of protection, that include making Ana be watched by a bodyguard on his payroll at all times and literally forcing her (he picks her up and starts carrying her away while they're in the middle of the street) her to move in with him.
* In ''The Beast Within: Literature/ATaleOf Beauty's Prince'', to bring about the Beast's downfall, the witches seem to think the best way to go about things is to make Belle homesick and hope that the Beast thinks to give her the mirror as she lives, ''then'' tell Gaston to have her father committed by introducing him to their friend the asylum owner, ''then'' anticipating Belle revealing the Beast to everyone, then expect Gaston to go kill him. Apparently all that was a better plan than casting an enchantment on Belle (they use magic to make her miss her father, so it's not like they couldn't do that) or even having the asylum owner forcibly commit her directly. Keep in mind that the last petal falls from the rose that very evening, so really they would have succeeded in making the curse permanent simply by having Belle spend the night tending to her father!
* ''Literature/GentlemanBastard'': Conman Locke Lamora admits that he's completely unsatisfied with simple, safe and reliable schemes. He always dreams up big and grand designs that might earn a fortune or might burn down a whole neighborhood. Sabetha bristles under the fact that she earns about as much as Locke over the long term, but his plans are so complex, ambitious and ingenious that he gets all the attention from their master.
* ''Literature/TheSpiritThief'': Eli loves to make his schemes as ridiculous and complicated as possible, which trips him up several times when he thinks his opponents love theatrics as much as he does. Justified partly by his desire to earn a bounty of one million standards, which requires him to be very flashy and audacious.
* ''Literature/TheThinkingMachine'': This is the only thing that can explain the incredibly convoluted plan the criminal comes up with in "The Fatal Cipher". It actually relies on the fact that Van Dusen is a deductive genius to stand any chance of succeeding.

[[folder:Live-Action TV]]
* ''Series/AgentsOfSHIELD'':
** Victoria Hand in "[[Recap/AgentsOfSHIELDS1E7TheHub The Hub]]". She sends Ward and Fitz on a mission to disarm a weapon that has fallen into terrorist hands, with the promise that they will be extracted afterward before S.H.I.E.L.D.'s takeover of the facility. In truth, however, there is no extraction plan and Ward and Fitz are likely going to their deaths. When Coulson confronts her about this, she merely states that they couldn't spare the resources. In the end, Coulson decides to go against her orders and take the rest of his team to rescue Ward and Fitz. Hand then reveals that she intended for him to do this all along... which begs the question of why she didn't just order Coulson to extract Ward and Fitz in the first place, since that's apparently what she wanted and (at least as far as the viewers are aware) it's not like Coulson and the others were really doing anything at the Hub to begin with. Heads into GambitRoulette territory when you consider that Coulson wouldn't have even found out there was no extraction plan if Simmons and Skye hadn't also violated their orders and hacked into Hand's classified mission plans.
** In a later episode, Hand reveals that she's been evaluating Coulson to determine whether he CameBackWrong, so the events of "The Hub" might have been a SecretTestOfCharacter (though still an overly-complex one).
* Everyone in ''Series/AlloAllo'' has this, with every plan from Michelle or the Commandant having at least three steps too many. Stand out has to go to Herr Flick's plans though, at least Michelle and the Commandant are usually ''trying'' to be discreet seeing as how they are breaking the law. Herr Flick just likes to plot things.
* In ''Series/{{Angel}}'' Jasmine's plan while possessing Cordelia gives the impression of being massively over-complicated. Apparently, she felt the need to unleash the Beast, make Connor think he was responsible for the apocalypse, have sex with him, blot out the sun, bring back Angelus, release him to generate even more chaos and possibly kill the Beast, which serves her, then give birth. Alternatively, she could have had sex with Connor, told Angel, "I need some time to think", and left the city for a [[ExpressDelivery month or two]].
** One possible justification for this is that actually ''required'' the deaths the Beast caused to bring her forth, and that Jasmine lacked full control in the early days. This would also explain why "Cordelia" had a nightmare (which the audience saw her having inside her own head) about a monstrous unknown demon--that ''works for her'' and she told to show up.
* In one episode of ''Series/TheBigBangTheory'', Sheldon develops a game of three-person chess, then starts adding new pieces, new abilities... it quickly [[{{Calvinball}} spirals out of control]]. Naturally, the gang loves it.
-->'''Leonard:''' When is my pawn allowed to use the golf cart?\\
'''Sheldon:''' When it's done charging. Or you land on the time machine... obviously.\\
'''Leonard:''' Oh...oh! Beekeeper to king twelve, I capture pope and release the swarm. Checkmate on Sheldon!
* ''Series/BurnNotice'': The organization that burns Michael has a really complex recruitment process involving burning spies and then doing all manner of things to force them to cooperate and do their dirty work. Surely they could have just found some operatives they could tempt with money?
** As it turns out, [[spoiler:the guy running the show is a psychologist with access to classified dossiers on agents. Which means that he can profile them to see if they're a good fit. Needless to say, with Michael it eventually backfired horribly]].
* Presenter Tim Shaw has this in his ''CarSOS'' show during the segment he returns restored cars back to their owners. He always goes for the most convoluted scheme, complete with cheesy disguises and fake personae, possible; once even including a full pipe band in order to disguise a car's unique engine note. His co-presenter Creator/FuzzTownshend lampshades it as Tim just liking to dress up and being frustrated {{Pantomime}} dame.
* Some of the [=UnSubs=] of ''Series/CriminalMinds'' are pathologically stylish. The one that comes to mind first would be the Fisher King, who, for some reason, decided to send the protagonists on a Myth/KingArthur-themed scavenger hunt to catch him and save his victim, [[spoiler:who was also his daughter]].
* One episode of ''Series/CSICyber'' involved a man who wanted to murder the witnesses whose evidence had put his father in prison. The obvious solution was, or course, to become one of the most skilled players of an online first person shooter, use his hacking skills to remove inventory items from accounts of some of the other top players (who had to be adolescents living in the same city), befriend these players by gifting them replacement gear (hacked from yet more players), spend hours a day playing with them to gain their trust and then use them to unwittingly courier disguised firearms that he had ordered from the deep web and hide them in appropriate locations so that he could later retrieve the guns in order to shoot his targets. The point of all this was apparently so that the firearms would be untraceable but that is hardly the only challenging aspect of planning a murder and given the insane complexity of the plan it is difficult to believe that he couldn't have got hold of the illegal guns some other way (plus of course the cyber team are able to track him down anyway).
* ''Series/DirkGentlysHolisticDetectiveAgency'': Dirk and Todd complain that Dirk's employer designed a needlessly complicated and dangerous verification system of death traps to give them the clues they need.
* ''Series/DoctorWho'':
** The Master, from both the Roger Delgado incarnation and (especially) the Anthony Ainley incarnation. As the Rani once stated, "he'd get dizzy if he tried to walk in a straight line!" This is an intentional character flaw; Creator/TerranceDicks says the joke with the Master is that he's "the man so intelligent that he can't see the simple things staring him in the face." This usually tends to blow up in his [[spoiler: or her]] face.
** Styggron in [[Recap/DoctorWhoS13E4TheAndroidInvasion "The Android Invasion"]] might have actually conquered Earth had he just sprayed the planet with the impossibly deadly poison that would certainly have killed every Human on Earth, rather than spend so much of his time dicking around with robot doubles, {{Gaslighting}} spacemen, and building hyper-realistic training simulations where the pubs are kept fully stocked up with ale but every day on the calendar reads the same date.
** It's a commonly pointed-out plot hole in [[Recap/DoctorWhoS13E5TheBrainOfMorbius "The Brain of Morbius"]] that Solon's plan to give BrainInAJar Morbius a new body is far more complicated than it needs to be. Much of the plot is driven by his intention to cut off the Doctor's "magnificent" head and use it as the final piece of the FrankensteinsMonster body that he built for Morbius to live in. It would have been a lot more straightforward just to [[BrainTransplant put Morbius into the Doctor's body]] -- or even Condo's. This was mostly a holdover from earlier drafts of the script in which Condo was absent and Solon was a robot stitching together bodies from downed spaceships with no understanding of how they looked together and the PlotHole was big enough that Creator/TerranceDicks wanted his name taken off the script. The production subtitles on the DVD suggest that, as someone who already spent a lot of time on the mishmash body, Solon may be experiencing "the same logic blind spot that engulfs someone when they are trying to assemble a flatpack wardrobe in that they would rather spend time and effort hammering in new bits, cutting off useless parts and searching for non-existent screws so that they can actually get the darn thing installed than start afresh with something far more suitable for the purpose intended".
** The Doctor himself occasionally falls prey to the disease. More than one companion has had to point him in the direction of the simple approach when he's started going a little too tangential in his solutions than is tolerable (or safe . . . or sane).
** The Silence's plan to kill the Doctor was extremely complicated. Apparently they were controlling humanity and manipulating the space race to get a space suit which their assassin would be in while killing the Doctor. This despite the fact that they are capable of time travel and seem to have a base in the 52[[superscript:nd]] century. However, there is a reason: they want the Doctor's death to ''[[KilledOffForReal stick]]'', and so need to arrange for the right place, to be able to make it a fixed point in time, and the right assassin.
* Happens on almost every episode of ''Series/{{Eureka}}'' as the super-scientists go through complex ideas to solve a major problem. It's non-scientist Carter who comes up with the solution so obvious and simple, it never occurs to the geniuses.
* Barney on ''Series/HowIMetYourMother'' puts way too much thought and effort into just about everything. When he wants to see whether he or Ted is the better TheCasanova he plans to have them compete in a sexual decathalon in a neutral city with a panel of international judges. When he wants to get revenge on Marshall, he spends months developing an exploding meatball sub to prank him with and uses elaborate and expensive means to fake a terminal illness so that Marshall will eat the exploding sub in accordance with Barney's last wishes. And that's not even getting into the ridiculous {{Batman Gambit}}s he uses to seduce women.
** The entire episode "The Playbook" is the explanation of ''one long scam'' on Barney's part to pick up a woman he hadn't even met yet when it started. It involves a scuba suit, website design, the Empire State building, seducing two other women along the way (one of whom he knew was a plant trying to scam ''him''), at least two false identities, and feigned emotional vulnerability.
** And, the short-arc plan "The Robin", where he had to eliminate Robin's current boyfriend, enlist her office frenemy, use a BatmanGambit on the rest of the gang, and finally get Robin positioned, just so he could ''ask'' her if she'd marry him. The final step: "[[spoiler:Hope she says yes]]."
* ''Series/TheInvisibleMan'': Arnaud is addicted to devising complex schemes for getting the invisibility gland out of Darien. In one episode Darien actually asks Arnaud why he hasn't just shot him or cut the gland out?
* This is Nate Ford's shtick in ''Series/{{Leverage}}''. Numerous characters have pointed out that he's addicted to running increasingly complex cons.
** Although unlike most of the other characters here, he is [[ManipulativeBastard sufficiently skilled]] that his plans usually work. This is helped by his [[BadassCrew extremely skilled associates]].
** In a season four episode, Hardison proves himself vulnerable to this, failing to complete a con because the marks began to suspect that the rigmarole was too extensive. Nate explains that he's able to be addicted to complexity because he begins from Plan G, the "ugly plan" that'll probably end up working even when everything else doesn't and that the other Plans help advancing.
* ''Series/MacGyver1985'': Karl, the bad guy in "Deadly Silents", seems to suffer from this; concocting several elaborate death traps to kill Mac and Pinky, even as his partner keeps urging to [[WhyDontYouJustShootHim just shoot him.]]
* [[spoiler:Morgana]] from ''Series/{{Merlin}}'' has this to the point of VillainBall[[note]]See the recap of "Castle of Fyrien", for one[[/note]]. Best summed up by this quote from the "Lancelot du Lac" recap page. [[spoiler:Oddly enough, in this episode it actually works to heartbreaking effect]].
--> '''Recap:''' Kill King Arthur? Nah, that's way too simple! Her plan involves soul coins, zombies, mind control, magical bracelets and perfect timing. It can't go wrong!
* Many of the killers on ''Series/{{Monk}}'' and ''Series/{{Psych}}'' fit this trope. Many come up with very elaborate schemes to kill the people they want dead. And although the end result is a mystery that leaves many of the cops stumped and the main detectives boggled for a few minutes, there were too many places for something to go wrong, which will ultimately lead to the clue that indicts them.
** [[Series/{{Psych}} Shawn]] even lampshades this:
--->"First, you tried to make him fail a drug test, then you tried to trade him off to other teams, and when those didn't work you tried to kill him...I guess just injuring him would have been, what, too Tonya Harding-ish for you?"
*** Possibly the case with recurring character Yang, as a symptom of her insanity. As a serial-killer her over-complex puzzles and riddles defeated every detective that tried to catch her, Shawn being the first one smart enough to win, [[spoiler: except it was actually her father who was performing the killings]]. But even in subsequent appearances where she is really trying to help Shawn catch her partner Yin, she ''still'' phrases her help in vague riddles and hints, rather than just ''telling'' him who Yin is. The one time he asks her to do exactly that, she becomes angry and insists that "that's not the way I work."
** "Mr. Monk and the Sleeping Suspect" is one particular case: Brian Babbage successfully kills his sister Amanda while he himself is in a coma that he's been in for several months. How did he do it? With a bomb that was stuck to the bottom of the inside of a mailbox with a special type of glue that would hold out for a few months, meaning it would be delivered on a time release, after which it would go off when it finally got into the deliveree's hands. The possibility of it being delivered to the wrong address, of the victim moving, or of the bomb detonating too early or not at all don't seem to occur to Brian.
* On ''Series/MontyPythonsFlyingCircus'', there is a sketch in which a group of gangsters plan complex intricate schemes to do perfectly legal and mundane tasks such as buying a watch from a store and withdrawing money from a bank. Only one of them questions why they are putting so much effort into doing legal acts.
* On ''Series/NewGirl'' Schmitt and Ceecee are helping Winston with what they think is a proposal to their girlfriend. They're surprised when he doesn't as Winston explains he has a "28-point plan" for the proposal.
** Winston enlists Jess' help cutting the list down and she starts tossing out items like erotic skywriting, the Los Angeles Children's Choir and a bobcat costume.
* During a stint of unemployment, Ben of ''Series/ParksAndRecreation'' invents a game called "Cones of Dunshire", but when he attempts to explain the rules to Leslie, he realizes that it is far too complicated and fears that ItWillNeverCatchOn. The game's complexity is exactly what endears it to the employees of an accounting firm that offers him a job. Much later it catches on more widely (although not among the cast), and the fact that he's the creator is what convinces a tech company to invest heavily in the town.
* SOP for pretty much every ''Franchise/PowerRangers'' villain. They almost invariably utterly outclass all of the Rangers put together, and could easily wipe them out on Day 1, but choose to go through a whole process of summoning a monster, sending it out, waiting for the Rangers to beat it, making it grow, then complain about not being able to beat those pesky Rangers. Repeat as necessary.
* A minor plot point in the season 2 finale of ''Series/{{Sherlock}}'': [[spoiler:In an aversion of HollywoodHacking, Sherlock is so convinced that Moriarty actually made a program that can hack into anything that he never once considers the possibility that Moriarty simply bribed the right people to open the right doors and set off the right alarms at the proper times to make it look like he had developed such a program]]. Moriarty is legitimately disappointed in Holmes for not figuring this out, and calls him out on it.
-->'''Moriarty:''' That's your problem: you always want everything to be clever.
** In Series 3, [[spoiler:Sherlock claims that this in turn was all part of an elaborate BatmanGambit cooked up by him and Mycroft to bring down Moriarty and his organization. [[MindScrew If that was really Sherlock]]]].
*** And then there's the finale of Series 3, a ridiculously complicated GambitRoulette[=/=]BatmanGambit[=/=]MindScrew which...suffice to say, left fans ''very'' divided.
* While the Goa'uld of ''Series/StargateSG1'' attempted to be this, they came off as just a bunch of {{Large Ham}}s what were TooDumbToLive. Ba'al, on the other hand, actually ''had'' this. In the DVD movie ''Film/StargateContinuum'', he had the means to crush the Earth to dust a hundred times over, but he wanted to conquer the Earth by inviting the US President to tea. When the other Go'auld simply wanted to bomb the planet, he mocked their lack of style, saying "You're all so stuck in your ways." You could seriously sometimes forget that you're '''not''' supposed to root for him. {{Justified}} twofold: one, Ba'al retains memories of [[spoiler:the original timeline where Earth is ''way'' more trouble than it's worth to the Goa'uld]], and two, [[spoiler:in the original timeline he spent about a year living as a human and [[HumanityIsInfectious sort of got to like it]]]].
* Discussed in the ''Series/{{Supergirl}}'' episode [[Recap/Supergirl2015S2E8Medusa "Medusa"]], regarding the [[Comicbook/LexLuthor Luthor family]].
--> '''Alex''': Why did Lillian Luthor take your blood? I mean, [[WhyDontYouJustShootHim why not just kill you]]?
--> '''Kara''': I... think she has something a little more nefarious planned.
--> '''Winn''': Ah yes, those Luthors do love an ''epic'' criminal scheme.
* A geopolitical version of this is critiqued in ''Series/TheWestWing'' episode "A Good Day". Over the course of the episode Kate comes to realise that the various military and political wonks in the White House Situation Room, including herself, are so used to dealing with crises that they've gotten themselves locked into a near-perpetual crisis mode that leads them to over-complicate every situation to at times truly ridiculous and even dangerous ends. Case in point: a couple of hunters accidentally crossing the border and finding themselves in a stand-off with Canadian police almost becomes a war between the United States and Canada because everyone involved reacts as if this is a major international incident requiring a military build-up, sabre-rattling, complex back-door diplomatic negotiations and lots of serious complex stratagems instead of just a couple of schmucks who got lost and bumbled their way into Canada. Kate eventually resolves the situation by... falsely telling the hunters that hunting season is over and if they don't knock it off and surrender themselves they'll lose their hunting licenses.
* What screws over the BigBad of the first season of ''Series/TheGoodPlace'': [[spoiler: Michael, the architect of the Good Place. He was so excited to build a Bad Place. But instead of building a normal Bad Place and filling it with mundane torture implements like fire and bears and "butt spiders" like his fellow demons, he had to get an idea. He designed a Bad Place where its inhabitants would unknowingly torture each other with their personality flaws while thinking they are in the Good Place. But to pull off such a grand plan he had to give the humans living there free will and maintain the illusion, which ultimately ruins the plan when the humans figure out on their own that they are in the Bad Place.]]
* Justified on ''Series/Deception2018'' as illusionist Cameron explains to the FBI that most illusions (and crimes inspired by them) tend to be ridiculously complex just for the hell of it in order to hide the truth from the audience.
** A Russian mobster makes people think they're on a fake reality TV show as a scheme to eliminate people who would try to defect from his organization.

* Quoth Peter Sinfield, one-time lyricist for Music/KingCrimson:
-->"We had an Ethos in Crimson...we just refused to play anything that sounded anything like a Tin Pan Alley record. If it sounded at all popular, it was out. So it had to be complicated, it had to be more expansive chords, it had to have strange influences. If it sounded, like, too simple, we'd make it more complicated, we'd play it in 7/8 or 5/8, just to show off."
* The premise of the Johnny Cash song "One Piece at a Time"...An automotive factory worker conspires with a friend an elaborate plan to steal an expensive sports car by sneaking the necessary parts off of the assembly line one at a time, spread out over multiple years and putting them together at home. Things become extra complicated when he realizes he didn't factor in the changes in car designs across successive model years.

[[folder:Tabletop Games]]
* ''TabletopGame/{{Warhammer}}'', ''TabletopGame/WarhammerAgeOfSigmar'' and ''TabletopGame/Warhammer40000'': Tzeentch, being essentially a god of {{Magnificent Bastard}}s, acts almost exclusively through {{Gambit Roulette}}s, even when a more straightforward solution might be possible. Many of his plans appear to be in direct conflict with each other, and it's been suggested that he doesn't actually ''have'' an ultimate goal. In fact, a popular fan theory is that Tzeentch has a LITERAL complexity addiction. If he ever wins, that is to say becomes the utterly dominant Chaos power and overruns reality, then there will be no more schemes for him to enact. Which will mean he ceases to exist at the very instant of his victory. That's why so many of his goals are in opposition to each other -- he cannot afford to ever actually win, but nor can he cease trying to. Mind you, he does seem to [[ForTheLulz enjoy it,]] as well...
** Before the Horus Heresy, Primarch Roboute Guilliman criticised Primarch Alpharius of the Alpha Legion for this -- Alpharius' elaborate plans may in narrow terms have been highly successful, thoroughly crushing all opposition with limited losses for his legion, but they were also wasteful in time and resources (not helped by Alpharius' tendency to sometimes take counter-productive actions like warning enemies and giving them time to fortify solely to make his victories look more impressive).
* ''TabletopGame/{{Exalted}}'''s Infernals suffer from Torment, which punishes them if they don't obey their (literally) Hellish masters. In order to appease them, they can perform Acts of Villainy that pander to their patrons' urges. Intentionally leaving clues to attract heroes to oppose you, setting up a fiendish death trap and gloating about your plans before leaving them for dead are all acceptable. Better still, you are rewarded whether or not you are successful; thus, rebellious Infernals can intentionally set themselves up to fail, in order to escape punishment for not doing their jobs.
* Tinker gnomes in ''TabletopGame/DungeonsAndDragons'''s ''Literature/{{Dragonlance}}'' and ''TabletopGame/{{Spelljammer}}'' settings have this. It's most obvious in the {{Rube Goldberg Device}}s they're (in)famous for, but they're perfectly capable of falling in love with just about any "brilliant" idea or scheme at a moment's notice as well. (Some examples of their [[TryToFitThatOnABusinessCard naming conventions]] would seem to indicate that their brains may indeed run a mile a minute -- they'd have to just to cope with all the information they try to put ''into'' a "proper" name -- they just do so without bothering to stop for common sense along the way.)
* A lot of CollectibleCardGame players focused on the creative deck-building side of the game are motivated by a desire to see their convoluted deck concept or some AwesomeButImpractical card actually win something, even if picking up a [[BoringButPractical tried-and-true cookie-cutter meta deck]] would have a higher success rate. Lampshaded by one such ''TabletopGame/MagicTheGathering'' [[http://gatherer.wizards.com/Pages/Card/Discussion.aspx?popularpage=4&multiverseid=230788 card]]:
-->'''Laboratory Maniac:''' His mind whirled with grand plans, never thinking of what might happen if he were to succeed.
** In ''Magic'', such people are called "Johnnies" or "Jennies", and they're viewed as one of the three main player psychographics (the others being Timmies/Tammies, who play for the experience of casting big creatures and entertaining spells, and Spikes, who play for tactical satisfaction and the joy of winning).
* There's a little bit of a complexity epidemic in ''TabletopGame/RocketAge'', as many villains won't simply shoot the heroes, they'll tie them under a Rocket Engine, unleash mutant collared peccaries, or thrown into an arena. There's even one instance of a group of fanatical but otherwise perfectly sensible Soviet agents putting a hostage on a furnace's conveyor belt.

* Cleopatra from ''Theatre/AntonyAndCleopatra'', she can't simply say something straight to your face or ask you for something, she'll make sure to manipulate your emotions and thoughts to get what she wants, even when it's completely unnecessary or even counterproductive.

* ''Toys/{{Bionicle}}'': Makuta's original plan failed. So he came with something even more complicated that required thousands of years of precise timing, careful execution, reliance on [[JustAsPlanned his opponents doing exactly what he expected them to do in trying to foil his schemes]], and even his [[ThanatosGambit own potential death]]. Some of his allies seriously complain about the over-complexity, wanting to simply use brute force instead, and a running joke among the Brotherhood was that he had back-up plans in place for his breakfast. Heck, Makuta himself even seemed aware of his addiction, as at several points he admitted to having "schemes within schemes" that would tear apart his enemies' minds if they tried to seriously decipher them (this is, in fact, NotHyperbole-look at Zaktan). [[spoiler:And it [[TheBadGuyWins WORKED]], with no one the wiser until he literally came out and revealed it]].
* The board game ''Mouse Trap'', where the {{Rube Goldberg|Device}} mechanism for catching the mice was so complicated that it rarely if ever worked.
** As [[http://www.youtube.com/watch?v=_dJr2SdyLGk the 1990's commercial]] describes the proceedings:
--->''Just turn the crank''\\
''And snap the plank''\\
''And boot the ball right down the shoot.''\\
''Now watch it roll''\\
''And hit the pole''\\
''Knock the ball in the rub-a-dub tub''\\
''Which flips the man''\\
''Into the pan.''\\
''The trap is set''\\
''Here comes the net!''\\
''Mouse Trap--I guarantee!''\\
''It's the craziest trap you'll ever see.''

[[folder:Video Games]]
* ''Franchise/SonicTheHedgehog'':
** Mephiles's plan from ''VideoGame/SonicTheHedgehog2006'' could have ended so early if he just [[spoiler:killed Elise, thereby releasing Iblis]], but he had to overblow the whole plot, making the entire plan completely useless. He had plenty of other options, too:
*** He could even have just [[spoiler:[[LetsPlay/SonictheHedgehog2006 cut up a few onions in front of her]]]].
*** He could have skipped the manipulation altogether and just merge with the clearly unleashed Iblis in Silver's time period. It's not like Iblis is being subtle and hard to find.
*** Even what he ends up doing, [[spoiler: killing Sonic]], would have been fine. Given the ease of which it was done, and that he only does it because his more complicated plan failed spectacularly, you have to wonder why he didn't just do that in the first place.
** Another example from the ''Sonic'' Universe is the Game Gear game ''Sonic Labyrinth'' a game where Sonic has to solve puzzle mazes by [[GottaCatchThemAll collecting]] [[MacGuffin keys]]. The catch is Sonic has lost his super speed with the exception of his spin dash ability, at the hands of his nemesis Dr. Eggman. According to the [[AllThereInTheManual manual scenario]] Eggman snuck into Sonic's house while Sonic was sleeping and stole his Sneakers to send him on this crazy quest.
** It's a general AcceptableBreakFromReality for villains to have large winding fortresses instead of just blocking the hero with a wall or [[LeapOfFaith having them fall into lava]], but special mention must go to ''VideoGame/SonicSpinball'', in which Robotnik builds a "Pinball Defense System" to stop his nemesis who is well known for curling into a ball.
* The Lich King in ''VideoGame/WorldOfWarcraft'' has a truly epic case of this. He comes up with a plan to [[spoiler: transform your player into one of his 10/25 (depending on dungeon mode) greatest generals by allowing you to train up by killing off any number of already competent servants, including his 10 most powerful minions you can only kill when outnumbering them at least 9 to 1, then slaughter your way up to his inner sanctum and nearly kill him, before he kills you and raises you as undead.]] Alternatively, his plan could have gone something like this: Lord Marrowgar....okay I made you too big to ever leave the room, stay where you are. Drakuru, who I didn't kill like an idiot, send out your super-trolls. Deathwhisper rally the cultists! Saurfang lead the troops! Putridus release your plagues! Unleash the Darkfallen! The other 8 billion of you...Charge! I mean seriously, [[TheAlliance those]] [[TheHorde idiots]] are still ''killing each other'' even though the sole reason you're here is to fight a guy who ''reanimates the dead''.
** This turns out to be explained by [[spoiler: what remains of Arthas' humanity deliberately holding him back. If the Scourge were left to their own devices (possibly still under the control of Ner'zhul) then they would wipe out the living. Possibly the ridiculous plan is a way to justify his [[OrcusOnHisThrone inaction]]. No, I'm not holding back. My plan just relies on bringing me to the brink of destruction]].
*** Also worth noting from the above, [[spoiler:Arthas' intervention]] appears to be in the Lich King's subconscious. Meaning [[spoiler: in his rational mind, the Lich King actually thought having 10/25 mortals farm his strongest generals and almost kill him, only to be killed and raised to serve him seemed like a good idea, and one that would have worked if he had the foresight to kill Tirion Fordring at the start of the fight as he easily could have]].
* ''VideoGame/DwarfFortress'' players in general ''love'' this trope. Why dispose of garbage by throwing it in a trash dump outside when you can reduce it to ash in magma or hurl it [[spoiler:into the bottomless pits of Hell]]? Why use a few [[GameBreaker cage traps]] when you can build a pressurized-magma WaveMotionGun? As for dealing with captured enemies... throwing them into a cavern or off of a tower is the ''simple'' way of dealing with them, but [[BloodSport gladiatorial combat]] and deranged {{death trap}}s are extremely popular as well.
** With any feature, intended [[GoodBadBugs or]] [[GoodBadBugs/SimulationGame not]], someone will find a way to weaponize it. Ignite artifacts to make incendiary booby-traps? Making drawbridge catapults to fire captive goblins at the next raiding party? Wait, let's drive a few dwarves berserk so they'll have to be slain and will come back as violently vengeful ghosts, which we can turn against our enemies! Or we could set up an elaborate gate-and-lever system (make sure you label the levers so you know where everything ends up) to both keep Noble politics interesting and the population of killer [[LegendaryCarp carp]] well fed!
** [[GameMod How about we start messing with the game files]]? Like increasing the body temperature of the common cat to create a trap based on cats breeding to a critical mass and the ensuring temperature rise wiping whole sections of the fortress of life/flammable material? How about making elephants breed faster with a higher body temperature and making that cat nuke into a medieval ICBM? Even better--let's use strengthened doors and an invasion from Hell to flush the fortress of pesky kobold thieves!
* In ''[[VideoGame/{{Superman 64}} Superman]]'' for the Nintendo 64, Lex Luthor captures Superman and puts him into a virtual reality environment, challenging him with tasks such as [[PassThroughTheRings flying through rings]]. Given the quality of the game, he may have been going for a FateWorseThanDeath angle here.
* ''Franchise/ProfessorLayton'', in the series named after him, when given responsibility over something, will want to do it in a time-consuming and convoluted way. This is most notable in the hamster he has to get into shape for ''Professor Layton and the Diabolical Box'', where Layton collects seemingly random junk to put in the critter's cage. Layton also likes to explain things to [[TheWatson Luke]] in the most confusing way possible. It's a good thing Luke is almost as good at deciphering messages as Layton. The villains aren't much better - in particular, Descole's convoluted schemes to find [[spoiler: The Azran sites]] before Layton, and [[spoiler: protect them from Targent]]. Especially his plan in ''Eternal Diva''.
* People who play ''[[VideoGame/Aurora4X Aurora]]'' live by this trope, with the game being so complex any lesser person will go mad from frustration.
* General Viggo from ''VideoGame/FurFighters'' opens the game by gassing the Fur Fighter village, knocking them all out cold with sleeping gas. He then kidnaps the children as hostages and transforms the spouses into mutant monsters to guard key locations. The reason for not killing the titular heroes who are currently helpless? Because that always went badly in the past. By the end of the game he decides to stop with all the clever plans and just use brute force.
* There's one particular scenario in ''VideoGame/RideToHellRetribution'' involving the player having to get past an electric fence. The solution, instead of just crashing through it with a vehicle or cutting the power nearby, is to go kill a bunch of truckers, steal their fuel truck, kill a bunch of cops when they come to stop you, drive out of your way to a nearby power plant, kill everyone there and crash the truck into the power plant to destroy both, before returning to climb the un-electrified fence.
* The AntagonistTitle character in ''VideoGame/BatmanArkhamKnight'' has a chance to kill the other title character upon first meeting him, but [[BondVillainStupidity chooses instead to tell the guards to leave him alive, so he can make him suffer]]. Somewhat justified in that he's working with Scarecrow, who wants to destroy Batman's legacy, [[DontCreateAMartyr which killing him would make more difficult.]]
* The [=PS2=] FPS game ''Daemon Summoner'' has a stealth level which requires you to sneak on board a ship, and despite it being close to your starting position and only having one guard, you have to take the most roundabout and out of the way path imaginable to get on board the ship by sneaking through a warehouse, up a ridiculously long staircase and over the roof.
* One complaint levied against ''VideoGame/ShadowOfDestiny'' is the ways the main character avoids death seem like an excuse to abuse time travel. A video game magazine cited one scenario: the main character, Eike, is standing next to a tree when he is killed by an assailant who was using the tree to hide. Because of the circumstances of the game, he can move through time to prevent his own death. His solution? Go ''back to when the seed was first planted and prevent the tree from growing'', thus rendering his assassin's mode of concealment moot. The solution the magazine proposed? Just not stand next to the friggin' tree.
* ''VideoGame/TheSecretWorld'': Justified with one of the main factions, the Dragon. Since they are students of Chaos Theory, in many cases the only point of their plans is to test their models. So they will set some ridiculously complex plot into motion just to see if it works. If it doesn't, they still get to gather data, and they'll be sure to do better next time.
* Pierce of the ''VideoGame/SaintsRow'' series is fond of devising needlessly convoluted plans that are always ignored in favour of the Boss's preferred method of "barge in and spray bullets until everything is dead". His loyalty mission in ''VideoGame/SaintsRowIV'' is about finally going along with one of his plans for once.
** In the alternate reality spin-off game ''VideoGame/AgentsOfMayhem'', Pierce ended up in charge of the Vice Kings and it's shown that his complicated plans actually did work exactly as intended, allowing him to eventually perform a bloodless takeover of all of Stillwater's criminal element before being recruited into MAYHEM.
* In ''VideoGame/GrandTheftAutoSanAndreas'', the infamous "Supply Lines..." mission has Zero send CJ to humiliate his rival Berkeley by assassinating his couriers using a miniature plane that regarded as ThatOneLevel due to being very hard to maneuver, quite fragile and overall impractical for the task instead of a more conventional method like personally gunning them down, like what CJ has been doing for the entire game. In fact, Zero could very easily ask CJ to get rid of Berkeley, but he would rather prefer to prove his superior intellect instead.
* ''Franchise/KingdomHearts'': [[ArcVillain Master Xehanort]] could give the aforementioned [[Manga/{{Bleach}} Sosuke Aizen]], [[Franchise/{{Batman}} Riddler]], etc., a run for their money in terms of KudzuPlot plans. Case in point: According to ''3D: Dream Drop Distance'', everything in the previous games has [[GambitRoulette somehow]] been AllAccordingToPlan via [[DiabolusExMachina secret]] powers that overlap [[spoiler:AssimilationPlot]] with [[spoiler:StableTimeLoop [[note]]He even went as far as to [[BeyondTheImpossible cause his own]] StartOfDarkness![[/note]]]]. ...Given that other, more-straightforward [[spoiler:TimeTravel]] methods have been demonstrated in a couple of games, one wonders why he didn't just look for them in order to exploit the [[spoiler:original Keyblade War]] instead of working so feverishly to [[spoiler:recreate it]].

[[folder:Visual Novels]]
* Many of the murderers in ''Franchise/AceAttorney'' are either too paranoid, prideful, or just plain crazy to pull off a ''simple'' murder. Then again, simple murders are often covered up by the strategic destruction/removal of evidence or witnesses seeing things and coming to the wrong conclusions which often leads to the case itself taking on this trope, even if the murder was as simple as a spur of the moment shooting.
** Florent L'Belle, the second culprit of ''VisualNovel/PhoenixWrightAceAttorneyDualDestinies'', concocted a ridiculously over-engineered plot that involved blackmail, a village merger, a LockedRoomMystery, and impersonation, all just to steal a valuable object to pay off his debt, when he literally has his own personal line of cosmetics that he refuses to sell despite the numerous offers which would almost certainly let him pay off his debt.
--->'''Apollo:''' (Yeesh, {{Rube Goldberg|Device}} machines have less elaborate setups than L'Belle's scheme...)
** This also applies to [[spoiler:Manfred von Karma]]'s revenge for [[spoiler:Gregory Edgeworth getting him a penalty on his "perfect" trial record: he shoots Gregory, takes on his son as a protege and raises him to be the very sort of attorney Gregory hated, then entices Yanni Yogi to help him murder someone else to frame Miles Edgeworth for it, banking on the idea that being caught up in a case so close to his father's murder would cause Edgeworth to confess to Gregory's killing (which von Karma knew Edgeworth mistakenly believed he did) and lead to Edeworth's imprisonment]]. That's quite some DisproportionateRetribution.
** Lampshaded in the fourth game:
--->'''Ema Skye:''' Why can't we have a normal, straightforward killing once in awhile in this country!?\\
'''Apollo:''' (I'll... pretend I didn't hear that)
* Gilgamesh in ''VisualNovel/FateStayNight'' shows up, effortlessly kills Caster, deflects Ilya's best attack, and sneers at everyone, but declines to kill them because he thinks Shirou's house is too shabby for a battle. He also refuses to kill Shirou and Tohsaka later because the house is burning down, which might make his ''clothes dirty.'' Gasp! He acts like this throughout the game and only goes straight for a kill in Heavens Feel because he's pissed about someone taking away his stuff ([[spoiler:as in, Sakura is eating the townspeople]]). Oh, and it doesn't work, clearly because he discarded his style. Nevertheless, he's the most dangerous Servant around. He is repeatedly stated to be the strongest servant [[spoiler: (he has copies of all the legendary weapons the others yield plus unique ones)]], and is only defeated because he failed to use his full strength off the bat due to wanting to toy with opponents or not considering them worthy of his exertion.
* Beatrice's bio in ''VisualNovel/UminekoWhenTheyCry'' comments that she has a problem with this. She gets so focused on the means to her ends, that she sometimes forgets the ends themselves.

[[folder:Web Comics]]
* In ''Webcomic/GirlGenius'' this is an affliction common to Sparks, whose enthusiasm for pushing the boundaries of science and creating amazing contraptions can sometimes blind them to the obvious. [[http://www.girlgeniusonline.com/comic.php?date=20091019 Just so.]] Similarly if you ask a Spark to make a coffee machine, you end up with ''[[http://www.girlgeniusonline.com/comic.php?date=20070618 this]]''. They're so obsessed with building or improving new and crazy machines just to make them more complex, some even work in their [[http://www.girlgeniusonline.com/comic.php?date=20040405 sleep.]] The affliction is also part of their ego. Providing a MundaneSolution to a problem will get you, ''[[CoolAndUnusualPunishment at the very least]],'' a [[DeathGlare severe glare]] for [[http://www.girlgeniusonline.com/comic.php?date=20091019 having spoiled the fun.]] Airman Higgs lampshades it [[http://www.girlgeniusonline.com/comic.php?date=20150930 here.]]
* In ''Webcomic/GunnerkriggCourt'', as a result of her time in [[spoiler:the forest]], Antimony developed a case of this.
-->'''Antimony:''' I suppose this calls for... an even '''more''' convoluted scheme!
* ''Webcomic/{{Homestuck}}'': Vriska loves to brag about her many "irons in the fire", but she doesn't appear to care if any of these schemes actually ''conflict''; as long as she's got another pie to stick a finger in, she's as happy as a clam that's never heard of chowder.
** Her elaborate courtship of Tavros included abusing him physically and mentally, crippling him, taking advantage of his childhood fantasies, teaming up with him, mocking him, giving him a flying car, trying to force him to kill her and [[spoiler:killing him when he fails]], all in order to toughen him up and spark either red or [[FoeYay black]] romantic feelings [[spoiler:because she thought it was fated because of Mindfang's journals]]. Instead, he just got confused and very frightened of her. She'd have had better results by ''just being nice to him''--it worked on John.
** Rose tends to attribute a complicated motivation to those around her when a simpler one may be much more accurate and as more obvious. For instance, she thinks her mother's smothering affection and similar interests are affected in order to subtly mock and belittle her in an endless passive-aggressive battle of wits. Dave correctly guesses that Mom Lalonde's really just overly affectionate and happens to have the same interests as Rose.
** Caliborn takes this UpToEleven. Pretty much anything he does will be done the most needlessly-convoluted and time-consuming manner possible. Multiple characters point out his tendency to do things in ways that would mind-numb anyone else into a RageQuit.
*** This is one of the ways he's contrasted with his future self, [[spoiler:Lord English]]; whereas Caliborn wastes his time and skill on pointlessly complex schemes, [[spoiler:English]] has grown up enough to understand that [[TheJuggernaut he can just blast his way through anyone that tries to stop him]]. He still goes through a lengthy process to enter new universes, but only because he has to follow Sburb's rules. Plus he's immortal and a time-traveler, so it's not a big problem for him.
** John succumbs to this with his sylladex later in the story. After having spent most of the comic screwing around with his [[AwesomeButImpractical stupidly impractical, near-useless inventory system]] that forces him to constantly rearrange things, he gets his Dad's wallet sylladex, which is [[BoringButPractical simple, easy-to-use, and has loads more space]]. John responds to this by combining the two systems, [[IdiotHero making the whole thing even more hideously impractical just to make things more challenging]].
* ''Webcomic/TheOrderOfTheStick'':
** Nale has this as his standard ''modus operandi'' to the point where all of his plans are regularly described as "needlessly complicated" by other characters. [[http://www.giantitp.com/comics/oots0255.html Case in point]]. As seen above, he [[http://www.giantitp.com/comics/oots0725.html inherited this from his mother]] ([[LamarckWasRight even though she didn't raise him]]). Even his class (multiclass Fighter/Thief/Sorcerer specializing in enchantment spells) is the same as a Bard (his twin brother Elan's class) but more complicated.
** His father, General Tarquin, has a long-running scheme to rule the Western continent by acting as an EvilChancellor to one of the assorted petty kingdoms in the land while his friends manipulate two other kingdoms, occasionally letting them fall and moving onto another one. But he only resorted to that plan after straightforward military force failed and he writes off one of Nale's plans as "having too many moving parts."
** Xykon is the opposite of this trope, having a [[WhenAllYouHaveIsAHammer simplicity addiction]]. He sees no point in creating elaborate plans or strategies when he can simply bombard an enemy with high-level spells or a target with [[ZergRush thousands upon thousands of Hobgoblin soldiers]]. In Xykon's case, it's not just a matter of laziness. To him, not needing plans or strategies to defeat his enemies is the ultimate expression of power. He also has a extreme disdain for [[UnequalRites uppity wizards who treat sorcerers such as himself as magical imbeciles]]. Thus the above simplicity addiction is one of his ways to continually reject the wizard's way of life by succeeding with only the minimal of planning and intelligence. That's not to say his plans are stupid by any means. By creatively using a single spell he manages to destroy a very large chunk of the Sapphire Guard who are guarding the throne room.
* ''Webcomic/TalesOfTheQuestor'':
** The Fae, at least the Unseleighe Fae, trend toward this. Princeling Dolan had an ongoing political scheme that involved the Racconans, the Duke, the Wild Hunt, a minor plague, an unpayable debt and the daughters of a rival Fae Princeling and had been unfolding for over a century. As Sam put it, "(The Unseleighe Fae) think like a corkscrew."
** The Brotherhood of Beither are possible candidates as well. It currently appears that they used political intrigue and influence through the Archivist's Guild and the Expansionist Party to remove political rivals from power by dissolving their rival's constituency by destroying the town of Freeman Downs through a loophole in an unfulfilled contract....
* The fae of ''Webcomic/{{Roommates}}'' are no better. For example a simple installment of the custody battle between the Erlkönig and his ex Jadis involved BloodMagic, {{Shadow Archetype}}s, a magical mercenary doppelgänger, a cursed ring, an elaborate DreamWithinADream LotusEaterMachine, wrapped in several layers of symbolism, including planting ideas hundreds of years before, etc.... they both have a terminal case. (They are also incredibly [[LargeHam hammy]] and have the power to intentionally invoke several "Rule Of..." tropes.) Speaking of the Erlkönig. He is one of the few, who bother with human disguises. But it has really obvious flaws[[note]]still having slightly pointed ears, a shadow that shows his true form, using "Figlio Perduto" as ringtone, going with the alias Lord ''Er''ro''l'' ''King'', etc.[[/note]] which either means he is leaving clues so this trope, or the proof that he is [[GlamourFailure really]] [[MostDefinitelyNotAVillain bad at disguises]].
* Chaos in ''Webcomic/ElGoonishShive'' actually deliberately makes her plans unnecessarily complex and unreliable, largely because [[PrescienceIsPredictable the alternative is too boring for her]]. In fact, it's easy to argue the actual ''goal'' of her plans is to fail, and her nominal goals are chosen not so much because she wants to achieve them is to give the [[AchievementsInIgnorance greatest degree of freedom]] for the consequences of her plans failing.
** Immortals, of which chaos is a part of, generally have to resort to such plans because they are bound to the ironclad empower and guide rules, thouh Pandora (Chaos' first chosen name) is one of worst in that regard
** Voltaire, another immortal did have the simpler plans A and B, he enacted planc CM (AKA Complicated Mess) in desperation, though it turned out he didnt need it because something else did it for him and it was even easier to do then his first two plans, and now he is stuck executing a overly complex plan he doesn't need because he cannot stop it.
* Voldemort's tendency toward this kind of thing in ''Literature/HarryPotter'' is parodied in ''Webcomic/SluggyFreelance'' in the story "Torg Potter and the Giblets with Fiber". Millard Stoop (a parody of Voldemort) originally planned to curse the infant Torg Potter with a combination of curses that would make it into something small and forgetful that would constantly pee itself and spread the common cold to others. Yes, he was going to do this to a ''baby''. Also, the plot of the whole chapter is an elaborate BatmanGambit just like in the original (''Goblet of Fire'') to obtain some of Torg's blood... which ''starts'' with obtaining some of Torg's blood in order to enter him into the Try-Gizzard Tournament.
* ''Webcomic/{{xkcd}}'' brings in someone with one of these for "[[http://xkcd.com/1172/ Workflow]]". Configuring your system to interpret "hold spacebar" as "control" is reasonable. Making this configuration depend on a bug that overheats your computer is, in the admin's own words, horrifying.
* In the climax of ''Webcomic/{{Concession}}'' it turns out that what Joel thought was a carefully planned out XanatosGambit, [[http://concessioncomic.com/index.php?pid=20101029 had too many loose ends]]. [[spoiler: And it was all for naught, he believed that he needed to do all that to gather enough spiritual energy to overwhelm his older brother's powers, when his brother had no powers whatsoever. He could have just caused him to suffer an accident like all the other people he killed just to prepare for it.]]
* The team in ''Webcomic/SturgeonsLaw'' have a problem with something as simple as [[http://sturgeonslaw.net/comic/checking-in/ checking in]] to a [[http://sturgeonslaw.net/comic/fluency/ hotel]].
* In ''Webcomic/LeagueOfSuperRedundantHeroes'', SmugSuper Asstronomous got cursed by Maroon Jackdaw to have [[http://superredundant.com/?p=1110 the head of a donkey.]] Rather than [[http://superredundant.com/?p=1123 apologize]] and promise to stop hitting on her and the other superheroines at the [[GoodGuyBar Bar of Justice]], [[http://superredundant.com/?p=1128 he goes back in time]], finds an un-cursed version of himself, clones him, has his mind transferred to the clone and comes back to the present.
-->'''Asstronomous:''' What? Maroon Jackdaw was being completely unreasonable!
* ''Webcomic/DarthsAndDroids'': Jango Fett wants to kill Obi-Wan for murdering his partner. To that end, he comes up with a plot involving a clone army, to tear down the entirety of the Jedi Order, the Republic, everything Obi-Wan loves and cares about... and then he will kill him. His son even asks WhyDontYouJustShootHim It's because Jango's a CardCarryingVillain, and he wants Obi-Wan to suffer. [[spoiler:It doesn't work out how he planned]].

[[folder:Web Original]]
* The EvilOverlordList, item #85:
-->''I will not use any plan in which the final step is horribly complicated, e.g. "Align the 12 Stones of Power on the sacred altar then activate the medallion at the moment of total eclipse." Instead it will be more along the lines of "Push the button."''
* The eponymous Dr. Horrible of ''WebVideo/DoctorHorriblesSingAlongBlog'' feels that "killing is beneath him", and, as a result, uses non-lethal weapons such as the freeze ray. [[spoiler:At first, anyway...]]
* Accord of ''Literature/{{Worm}}'' is a supervillain with the power to solve a problem more quickly the more complex it is. In order to hold his interest, most of his plans tend to involve needlessly-complicated death traps. He also has [[CutLexLuthorACheck a twenty-three-year plan to end world hunger]] that no one will listen to.
* Tom Collins in ''WebVideo/DemoReel'' doesn't just kidnap Donnie, hold him hostage and force Rebecca and Tacoma to give up the show that way, instead he has his associates dump him in the woods, which results in the rest of SWAG leaving in disgust, Tom going through SanitySlippage and ends up with a beatdown from Rebecca, Donnie and Karl.
* Gavin Free of ''WebVideo/AchievementHunter'' has this problem sometimes, going for grandiose or flashy gimmicks when it would be better to do something simple. This is most evident in the group's various Let's Plays of the ''VideoGame/{{Worms}}'' series, where a well-known running gag is him using the grappling hook or jetpack to drop bombs on people which more often than not causes the death of his own worm instead when he panics and lets go at the wrong time. A more recent example would be in one of their Let's Plays of the Terrorist Hunt mode of ''VideoGame/RainbowSixVegas'', where he continually uses breach charges on doors just because it's cool instead of just opening them. The last time this happens he ends up ''killing a teammate.''

[[folder:Western Animation]]
* The scams in ''WesternAnimation/EdEddNEddy'' are this. The Eds are shown to have amazing talent in setting up services, but Eddy continuously insists on cutting corners with flashy scams that ultimately make the kids want to have a refund. It would be easy if they just set up an honest business, especially with all that technology Edd makes from junk. Case in point, any success they had is from a scam that's pretty straightforward while Jimmy succeeded on his first try with a trampoline.
* In ''WesternAnimation/AvatarTheLastAirbender'', EvilChancellor Long Feng has secretly ruled Ba Sing Se for years by suppressing all knowledge of the Fire Nation's war against the rest of the world. When the Avatar shows up, he finds himself in a position where he can't simply silence the Avatar and can't accept the Avatar's help without admitting the war is real. Instead, he has them followed constantly, captures Appa, then tries to get them to leave by lying about Appa's whereabouts. Had he just taken their intel but refused their help, then given them Appa, he wouldn't have been deposed at the end of the season.
* Slater from ''WesternAnimation/{{Archer}}'' seems to suffer from this: In "Pocket Listing" he needs to scan the handprints, retinas, cell phones and flash drives of a visiting prince while he is in New York. So he comes up with a ridiculously over complicated plan that involves luring the Prince and his bodyguards to Cheryl's mansion, having her pose as the listing agent while the rest of the gang pose as servants, having Ray use a laxative to separate the prince from his bodyguards, separating the prince from his incredibly overbearing mother, then drugging the prince with a dart gun and scanning all of this in the roughly sixty seconds that it will take for the drug to wear off... Even though it would probably be infinitely easier to simply break into his room while he is sleeping and scan all the electronic equipment and then drug the prince and scan his retinas and handprints.
** At the end of Season 6, [[spoiler:it's implied that Slater's been exploiting this trope in order to sabotage the gang so that the CIA could fire them for incompetence]].
* ''WesternAnimation/TheSimpsons'':
** "The Computer Wore Menace Shoes" (during a parody of ''Series/ThePrisoner''):
--->'''Number 2:''' I'll be blunt. Your web page has stumbled upon our secret plan.\\
'''Homer:''' That's impossible. All my stories are bullplop. [[GoshDangItToHeck Bullplop]]!\\
'''Number 2:''' Don't be cute. I'm referring to the flu shot exposé. You see, we're the ones loading them with mind-controlling additives.\\
'''Homer:''' But why?\\
'''Number 2:''' To drive people into a frenzy of shopping. That's why flu shots are given just before Christmas.\\
'''Homer:''' Of course. It's so simple. Wait, no it's not. It's needlessly complicated.\\
'''Number 2:''' Yes, it is.
** Subverted in another episode when Sideshow Bob's brother Cecil is about to kill Bart by throwing him off a hydroelectric dam:
--->'''Cecil:''' At last, I'm going to do what Bob never could: KILL Bart Simpson!\\
'''Bart:''' By throwing me off a dam? Isn't that a little crude for a genius like you?\\
'''Cecil:''' Ooh, I suppose it is. Eh. If anyone asks, I'll lie!
** Speaking of Sideshow Bob, there was that time he rigged the Springfield Mayoral Election by [[VoteEarlyVoteOften stuffing ballots]] ([[DickDastardlyStopsToCheat even though his opponent was guaranteed to lose anyway]]), and when he tried to kill Bart and Krusty with one stone by kidnapping the former, hypnotizing him, rigging him with explosives with triggers on his palms and having him try to hug the latter during what was supposed to be his final show.
** On ''another'' occasion, Sideshow Bob has Bart trapped in a coffin which is slowly being transported on a conveyor belt towards a crematorium furnace. That said, when the Simpsons arrive to rescue Bart, Sideshow Bob switches the lever from '''[[EvilGloating Gloating Speed]]''' to '''KillHimAlready''' to speed up the conveyor belt.
** In a Treehouse of Horror story, Homer learns that Moe has an emerald. He tries to get it by tricking Marge into marrying Moe and then he'll kill Moe and marry Marge to get the emerald. Homer says that the plan's best part is its simplicity.
* In an episode of ''WesternAnimation/{{Underdog}}'', Simon barSinister's plan to take over the city was thwarted because he couldn't reach a vital piece of equipment due to the UsefulNotes/ThanksgivingDay Parade blocking the street. Fortunately, he has a time machine. How does he use it? Option A: Go back in time to that morning, cross the street before the parade starts. Option B: Go back in time one day, tell his troops the attack is postponed until Friday, when the parade won't be blocking the street. Option C: Go back in time one week, and move the device to the other side of the street, so the parade won't be an issue. What he comes up with is Option D: Go back ''several hundred years'' and sabotage the formation of Plymouth Plantation so that UsefulNotes/ThanksgivingDay never happens, and therefore the UsefulNotes/ThanksgivingDay Parade will not exist to keep him from crossing the street. He opted to try to alter centuries of history, possibly creating a ButterflyEffect that would cause the city he wanted to conquer to never exist in the first place, just to remove a temporary ''traffic obstacle''.
* Perennial Creator/HannaBarbera villain [[DastardlyWhiplash Dick Dastardly]] [[DickDastardlyStopsToCheat is the king of this trope]]. In his first appearance on ''WesternAnimation/WackyRaces'' he would always come up with elaborate plans to cheat his way to victory. Here's the kicker: he didn't need to do this at all. His car was ''several times faster than anyone else's.'' He could have won every race legitimately with ease, and in fact, each race begins with him surging to a huge lead. But he always stops in order to set up traps, which invariably end up backfiring and costing him the race. This pattern of behavior would carry on to all of his many other appearances: no matter who he's going up against, Dastardly's complexity addiction is his greatest enemy. He even refuses to win legitimately: he's such a CardCarryingVillain that he can't stand to win if he didn't cheat while doing so.
** Another fine example was when Dastardly was given his own spinoff series. It revolved around him concocting ridiculously complex plans and inventing insane flying machines, all ''to catch a pigeon.''
** Also, ''WesternAnimation/ThePerilsOfPenelopePitstop'' kept seeing the titular character captured and put into overly ridiculous deathtraps. Granted the guy responsible wants to inherit her fortune and is probably trying to make it look like an accident (hence the reason he doesn't just shoot her), but some of them just get outright absurd, and after putting her in whatever trap he just runs off rather than sticking around and making sure it works.
* A heroic example: In ''WesternAnimation/TheAmazingChanAndTheChanClan'', Tom Chan will often suggest needlessly elaborate plans such as deploying a series of mirrors to examine a statue (when Anne can just climb the tree and look through a pair of binoculars) or catapulting them over a wall (when the gate's open). Mostly PlayedForLaughs.
* On ''WesternAnimation/PhineasAndFerb,'' [[MadScientist Dr. Doofenshmirtz]] will regularly plot to do something needlessly complicated rather than something ''much'' simpler, like steal Big Ben rather than go to the store and buy a new watch. [[BetterThanABareBulb It's often]] [[LampshadeHanging lampshaded]].
** Phineas and Ferb are prone to this as well. For example, in "Picture This", Ferb has left his skateboard in England:
--->'''Phineas:''' I know! We could create a highly-intricate and sophisticated machine that will transport any object from anywhere on the globe to our backyard!\\
'''Dad:''' Well, why don't you just build a new skateboard?\\
''[Phineas and Ferb stare at him in silence]''\\
'''Phineas:''' Hmm, yeahhh, I don't think so.\\
'''Ferb:''' If it's all the same with you, Father, we're going to build the machine.
** For Phineas and Ferb, it's literally an [[FunctionalAddict addiction]]--Phineas goes into ''[[ICantBelieveItsNotHeroin withdrawal]]'' when they're forced to climb a mountain the normal way, with no crazy inventions, in "Bully Bromance Break-up". [[TheStoic Ferb holds up a little better, but that doesn't mean he likes it]].
---> '''Ferb:''' If we hadn't been able to invent something soon, I was going to ''scream''.
** Candace too. In the Christmas special, she decides that to make sure she gets Jeremy the perfect gift, she's going to trick him into writing a letter to Santa and then read said letter; she laughs and calls Phineas ridiculous when he suggests she just ask Jeremy what he wants.
* Most ''Franchise/ScoobyDoo'' villains succumb to this, and [[OncePerEpisode every episode]] ends with either them or the members of Mystery Inc. giving detailed explanations of how they were pulling off what they were doing, and why.
** In the ''WesternAnimation/ScoobyDooMysteryIncorporated'' episode "Mystery Solvers Club State Finals": the villain (revealed to be ''[[spoiler: WesternAnimation/TheFunkyPhantom]]'', of all people), goes into ''excruciating'' detail about how he carried out his plot, which turns out to be an overly-complicated way of [[spoiler: getting rid of his team so he can stop being a sidekick]]. This ''could'' be justified by the fact that the whole episode is [[AllJustADream just a fever dream Scooby's having]], but still...
** In the following episode, the VillainOfTheWeek's plan is even more complicated, and more pointless. The Gang lampshades this.
** The reason why is generally something along the lines of "scare everyone else away so I can do what I want in the area," often involving treasure. Simply buying them off would work just as well, and would not attract people with an interest in ghosts.
** In the ''Mystery Incorporated'' incarnation the fact that everyone's plans involve costumes and monsters is overall lampshaded/explained by the fact that Mystery Cove is famous for hauntings, and the overall plot involves as cursed treasure (That would be a very strange curse). Everyone just uses monsters because everyone acts as if monsters are real until the reveal, the townsfolk, lead by the money grubbing mayor, never think to prove the monsters are real, they just try to make money off of them, justified by their tourist economy/haunted history. The whole thing is not always complexity addiction, sometimes it is a reasonable way to take advantage of everyone's unreasonable behavior. Though unless they are hiding something there is almost always an easier way.
* ''WesternAnimation/KimPossible'':
** Dr. Drakken suffers from this. His sidekick, OnlySaneWoman Shego, lampshades this repeatedly.
-->'''Shego:''' Okay, let's get Operation Too-Complicated-to-Actually-Work started!
** The AffablyEvil Señor Senior, Senior insists on sticking to [[CardCarryingVillain the code of classic villainy]] on principle, [[ContractualGenreBlindness even if it lets Kim get away and foil his crimes]]. Then again, considering that for him, this is an elaborate retirement hobby, it entirely fits that he's more interested in having fun and challenging himself by playing by the rules than actually succeeding. Notably, the one time it ''wasn't'' a hobby but an attempt to steal back his fortune after he was cheated out of it he went for a simple plan (use his extreme sport abilities to steal everything back piece by piece while pretending to be poor) that nearly succeeded. And when Kim was about to catch him his son Señor Senior, Junior ''succeeded'' with another simple plan: [[spoiler:claim the bounty placed on his father by the guy who cheated them out of their fortune and then hire a lawyer to take everything back]].
* ''WesternAnimation/SpongebobSquarepants'': This is pretty much Plankton's signature flaw when attempting to steal the Krabby Patty secret formula. From all his ridiculous schemes backfiring on him due to poorly timed planning, you would think by now that he would learn that all he has to do is just simply order a Krabby Patty. He can, but Mr. Krabs won't let him walk away with one, at least not one that's intact.
* ''WesternAnimation/AmericanDad'':
** Down to the [[EvilBrit Gary Oldman accent]]:
--->'''[[spoiler:Barry]]:''' You're not in any position to be calling the shots Steven; I'm the one holding the gun.\\
'''Steve:''' Sure, [[MundaneSolution you could kill me with your gun...]] but are you willing to try something much more elaborate and unnecessary?
** Roger also demonstrates this in the season seven finale "Toy Whorey." He goes through several elaborate plans to try to get a bottle of Rain Duck wine from Greg and Terry, such as using an elaborate RubeGoldbergDevice to cut the power in the Smith house and then just wait for the two to notice the blackout and come check on them. Eventually, Francine gets sick of waiting, goes straight to their house, bitch-slaps them with a spatula, and simply ''takes'' the wine.
*** An earlier episode had Roger enacting a scheme to steal a $10 pair of gloves, which involved buying a $700 necklace. His alter ego lampshades this, but Roger tells him to shut up.
** In one episode, in order to get into a local baseball stadium that he was banned from, Stan, rather than simply sneak or break in decides to: move to Cuba, become discovered by a baseball agent, get smuggled into the US, join a minor league team, get picked up by the New York Yankees, become addicted to steroids, get caught, get dropped by the Yankees and then get picked up by the team that plays in the stadium late in the draft.
* [[MadScientist Dr. Two Brains]] from ''WesternAnimation/WordGirl'' has a really bad case of this. In one episode, he tries to build a ray to transform gold into cheese. (Two Brains really likes [[TrademarkFavoriteFood cheese]].) But the ray doesn't work right. Instead of changing gold into cheese, it changes gold into potato salad. So Two Brains invents a ray to turn potato salad into cheese. Then he and his henchmen steal gold, to turn into potato salad, to turn into cheese.
-->'''Word Girl:''' Doesn't that seen a little unnecessarily difficult? I mean, why not steal potato salad instead of gold? Or use the gold to buy the potato salad? Or why not just steal cheese in the first place?
** In the episode "Vocab-Bee," The Butcher has a bout of this and hatches a perfect plan to rob a bank that involves [[NoodleImplements a giant bowl of chili, a hippopotamus, a skywriter, a tightrope walker, polar bears, a garbage trunk, a trampoline,a french poodle, circus clowns, and a giant parakeet]]. It takes all day to set up and is foiled in seconds.
* ''WesternAnimation/BatmanTheAnimatedSeries'' has a memorable episode where Harley Quinn manages to make one of the Joker's theme schemes to kill Batman ''work.'' However, Batman manages to foil the improved and foolproof scheme by getting Harley to phone Joker to come see his death and impress him...but the Joker's huge ego [[TheOnlyOneAllowedToDefeatYou would not let anyone but him kill Bats]], this in spite of it being a worthy death. Just goes to show that stylish evil can and ''does'' work...but {{pride}}'ll get ya every time.
** The Clock King even surpasses the Riddler as an addict to overly complicated schemes, but he exhibited this even before becoming a supervillain. As Temple Fugate, he has a chain pocketwatch, a wristwatch, and at his office he has a grandfather clock and another clock at his desks.
* In ''WesternAnimation/TheFairlyOddParents'' episode "Back to the Norm", Crocker joins forces with Norm the Genie to defeat Timmy Turner. Rather than follow Norm's simple advice to, say, wish Timmy be sent to Mars, Crocker keeps coming up with a number of elaborate booby traps [[HoistByHisOwnPetard which keep backfiring onto Crocker himself.]]
* In ''WesternAnimation/RegularShow'''s "Steak Me Amadeus", [[spoiler:the Capicola Gang's]] plan for revenge on the park workers is printing fake Amadeus dollars (coupons to buy steaks at "Steak Me Amadeus") and sell them to Pops who would give them to the rest of the workers. When they want more cheap steaks, they would set up a meeting to exchange more Amadeus dollars and then ambush them. Their whole plan is dependent on the gang's desire for affordable steaks and apparently they didn't bother to take in account that if the park workers use these counterfeit coupons they would get trouble with the police and get arrested and won't have the chance to meet them. Rigby lampshades it:
-->'''Rigby:''' Dude, that's really weird.\\
'''[[spoiler:Capicola Gang Leader]]:''' Well, it worked, didn't it?
* Pretty much every plan come up with by the Legion of Doom in ''[[WesternAnimation/{{Superfriends}} Challenge Of The SuperFriends]]''. This was probably due to there being thirteen members and wanting everyone to seem like a participating member. It didn't help that the show's version of The Riddler had no purpose but to tip off the heroes how to beat the current scheme.
* In ''WesternAnimation/{{Wakfu}}'', [[spoiler:Qilby the Traitor]] tried to accomplish his goals with a rather complex plan that really wasn't necessary. Adamai even points out that [[spoiler:Qilby could have used the Eliacube to retrieve his sister's Dofus without relying on Yugo]]. He claims that he couldn't do it on his own because he was no match for the Dragon Phaeris. A claim that rings hollow when he and Phaeris actually fight and he proves to be an even match. In the end, Yugo calls out the villain on devising a needlessly complicated scheme when he could have easily defeated the heroes from the very beginning and claims that he did this because [[spoiler:he can't bring himself to actually kill his fellow Eliatropes or the Dragons. Deep down, Qilby just wanted to convince them to join him so they could all be friends again.]]
* In the season 2 premiere of ''WesternAnimation/MyLittlePonyFriendshipIsMagic'', it's made very clear that if Discord wanted to disable the Elements of Harmony, the only stuff that can beat him, all he has to do is swiftly touch each of the mane six to invert their personalities and make them unfriendly to one another. But that would be too boring for him, so he decides to lure them into a hedge maze, [[DivideAndConquer divide them]] with hedge walls, give them lectures on how [[VirtueIsWeakness how the elements they bear are either weaknesses or hyprocritical]], THEN hypnotize them to make them unfriendly with one another.
** The episode "Applejack's Day Off", shows Applejack has gotten to be this way with some of her chores, reflexively doing things to circumvent problems she fixed a while ago. Due to wanting to follow Applejack's instruction list to the letter, Twilight and Spike don't even manage to finish feeding the pigs by the time she and Rarity get back from their hour at the spa.
* In the ''WesternAnimation/GravityFalls'' episode "Double Dipper", Dipper lays out an elaborate plan (which later gets more elaborate, with the help of his clones) to ask Wendy to dance because [[CannotSpitItOut he's too nervous to simply ask her]] [[StatingTheSimpleSolution like Mabel suggests]]. Her tone gives the impression that this is a regular thing for Dipper.
* Lampshaded in ''WesternAnimation/{{Futurama}}'' by Robot Devil: "Ah, my ridiculously-circuitous plan is one-quarter complete!" Said plan being a ChainOfDeals that started by taking Bender's ass-plate in exchange for a horn nose. Bender uses the horn nose to deafen Leela, whom the Robot Devil offers a pair of robotic ears to so she can hear Fry's Holophonor opera. She agrees on the condition of giving him her hand [[spoiler:[[ReadTheFinePrint in marriage]], which allows the Robot Devil to negotiate the return of his own hands from Fry, who had won them in a game with the Robot Devil]]. Hilariously, a later episode reveals that going through this was unnecessary anyway, the Robot Devil has multiple replacement bodies anyway therefore he could have switched out Fry's hands for one of the ones from the extra bodies easily enough.
* [[CorruptCorporateExecutive Leonardo Leonardo]] suffers from this in the pilot of ''WesternAnimation/ClerksTheAnimatedSeries''; he's got a 63-step plan that starts with building the Quicker Stop across the street from the original Quick Stop; the final step ends with a pleasure dome [[SerialEscalation launching into space and nuking the Earth from orbit]].
* In ''WesternAnimation/DuckDodgersInTheTwentyFourthAndAHalfCentury'', Dodgers explains to the Space Cadet his route for finding Planet X, a convoluted path even he finds too confusing, judging from his reaction when the Cadet seems to understand it. Cadet suggests instead that they follow a series of planets that have been conveniently alphabetized.
* This is MC Pee Pants' MO in ''WesternAnimation/AquaTeenHungerForce''. His very first evil scheme is to release a rap single to get people eat tons of candy before instructing them to visit a warehouse and use their hyperactive sugar rush to power a giant drill to bore into the center of the earth, releasing demons onto the surface to partake in a diet pill pyramid scheme. And they get never any less overly complicated than that.
* A running gag in ''WesternAnimation/LesShadoks'' is the title characters' ridiculous and nonsensical so-called "proverbs". Among one of the most popular is: "Pourquoi faire simple quand on peut faire compliqué ?", which is a parody of the French counterpart to "Why make it complicated when it can be easy?" Guess what it means? "Why make it easy when it can be complicated?"!
* The [[AdaptationalPersonalityChange new version]] of Flintheart Glomgold ''WesternAnimation/DuckTales2017'' comes up with utterly ludicrous, overcomplicated plans, which is not a great personality trait alongside holding grudges eternally and obsessive hatreds. His plan to get rid of an annoying bore in "The Infernal Internship of Mark Beaks" involves disguises, sharks, volcanoes, a cruise line buffet, and a ''teddy bear''.

[[folder:Real Life]]
* Study the planning of the [[UsefulNotes/KatanasOfTheRisingSun Imperial Japanese Navy]] in UsefulNotes/WorldWarII--especially at Midway, but any operational plan they put out. Marvel at the widely-spread, mutually-unsupportive forces they apparently tossed onto the map at random. Overthinking plagued the Japanese at nearly every level during the war. After it became plain that the Zero fighter plane was becoming outclassed, the Japanese realized they needed a replacement. Japanese scientists and engineers indulged in over 40 different prototypes, each as implausible as the last and taken immediately back to the drawing board as soon as a newfangled improvement occurred. In the interim, the aging Zeros and their pilots were cut to ribbons by Hellcats and Corsairs.
** The military-industrial complex of ''every'' sufficiently large participant in the war had many instances of this trope up until considerably late in the war. Only those which happened to have better percentages of competent teams and officers and/or enough resources to afford countless costly mistakes managed to pull ahead.
** The celebrated admiral Isoroku Yamamoto in particular had a reputation for making plans that were elegant, yet still complex. Often, he pressured his superiors into accepting said plans by threatening to resign.
* George Washington had a problem with this. He was at his best when he was forced to improvise and think on his feet, at his worst when he had time to come up with cumbersome, overly-elaborate battle plans. Made him [[StrategyVersusTactics a better tactical general than strategic general]].
* Tony Hawk mentioned in ''Film/TheBonesBrigadeAnAutobiography'' that he wanted to do as much tricky skateboard maneuvers as he can, despite being criticised for it. The most prominent example being his evolution of his [=McTwist=]: First he did a [=McTwist=], then moved on to one foot [=McTwist=], then body varial [=McTwist=], until it ended in an ''ollie'' [=McTwist=], as in doing a [=McTwist=] with no hands grabbing the board!
* This is all too common among Database designers. There have been examples of what would be a simple database of just user [=IDs=] and addresses, but it had 45 tables, not counting the audit and archive tables.
** This is all too common among large corporations and institutions which have been using computers ever since the days of punch-cards, and which have often expanded to take in new and subsidiary companies which have brought their own legacy systems as part of the package. Instead of being sensible and rationalising things with a barnd new system addressing the new needs of the company from the bottom up, it is common to see patch after patch applied and [[RubeGoldbergDevice makeshift remedies introduced]], in order to take fifty years worth of overlapping and often incompatible systems and make them work. One major British bank which is prone to regular collapses of its automated banking systems and its ATM network is notorious for this and its IT systems are a model of Byzantine complexity and Heath-Robinson makeshifts. Similarly, a major telecommunications company in Britain has internal IT systems which are fiendishly overcomplex to use, anything other than user-friendly, temperamental, and prone to frequent embarrasing crashes. RuleOfCautiousEditingJudgement applies to naming the guilty parties.
** Some legacy database software is still based on command-line editing and positively arcane to use, to the point that companies don't even bother trying to teach new employees. Rather than replace it, corporate policy is to build interfaces on top of it -- meaning that anything not included in the interface still has to be done at the bottom level. Things get even worse when time moves on and jobs are deskilled, frequently leading to multiple layers of increasing abstruseness as one delves toward the core. Once the last remaining guru is promoted or resigns, a company may end up with costly emergencies and errors (ranging into six figures) because no one left understands the mess.
* In a very dark example, the [[SerialKiller Zodiac Killer]]'s reign of terror was marked by complex mathematical riddles, obscure clues to his identity mailed to the police, and endless hidden messages. His victims were selected by how they met mathematical patterns and geometric patterns drawn on the map instead of, for instance, personal bias or true hatred. The trail of death was the Zodiac's way of proving his mental superiority, so the complexity was more important to him than the murders themselves.