Complexity Addiction

"I'll turn him into a flea, 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 *evil laugh*, I'LL SMASH IT WITH A HAMMAH! It's brilliant, BRILLIANT, BRILLIANT, I tell you! Genius, I say!... Or, to save on postage, I'll just poison him with this."

- Yzma, The Emperors New Groove

A character (usually the villain) comes up with a ridiculously elaborate plot that is so meticulously planned out that it can't possibly fail...

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

There's a simple... um... explanation. This character has a Complexity Addiction. They are Genre Blind and addicted to trying Xanatos Gambits. They simply can't help but make an overdone, overblown plan.

Maybe they're insane. Maybe they're Ax Crazy. Maybe they're bored. Maybe they view it as being artistic. Maybe simple plans aren't as amusing or as evil or are just too boring for them. Maybe they consider their enemies worthy opponents and that only an equally worthy plan should be used to defeat them. Maybe they don't even know the reason. It's Funny, or it's Dramatic, or it's Cool; that's all that matters.

Expect a more Genre Savvy character to point out the existence of a simpler solution, often something along the lines of "Why Don't You Just Shoot Him?". These characters frequently suffer from Bond Villain Stupidity.

Compare to Idiot Plot, in which the plan requires everyone else involved to be an idiot, and works anyway. See also A Simple Plan, where a very simple plan should have worked but goes horribly awry.

Contrast Combat Pragmatist.

See also Didn't See That Coming and Cutting the Knot. Additionally, see Rube Goldberg Device for machinery built by people with a Complexity Addiction.

Anime & Manga

 * Aizen from Bleach has a bad case of this, but ends up subverting it. 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.
 * He didn't know he could do that in the first place. He only learnt of it afterwards, when he went off to study Kisuke's research, possibly for days, because he realised that Ichigo might actually be able to save Rukia. He did, but if he hadn't the plan would have worked, and as far as he knew when he set it in motion it was the only way. The possibility that Urahara might have another way of retrieving the Hyugoku may or may not have occured to him anyway, but since he already knew one way to make it work, he didn't see the point in looking for another that might not even exist.
 * It's true he does suffer from this... at the same time, he failed to kill a number of targets his plan would leave dead (with no sign that he'd been responsible), failed to flawlessly cover his tracks (the Soul Society should have been completely unaware of what had really happened and been blindsided when he was ready to attack from the outside), and was forced into just grabbing the MacGuffin and making a clean getaway. His original plan had a lot of advantages over direct action; the opposing Gambits simply were effective enough that those went unrealized.
 * The Hueco Mundo arc is where he really succumbs to it. Aizen builds up an entire 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.
 * It's actually starting to shape up that the entire arc was just him biding time and making damn sure he wasn't beaten before the MacGuffin fused with him.
 * There is one other thing he got out of it- he sealed Yamamoto's powers with Wonderweiss. Arguably, the good guys suffer from this too. Rather than just have their two or three captains cut through the fodder to save time, they decided to do a Good version of Sorting Algorithm of Evil, just so that the lieutenants would get some screentime.
 * Mazinger Z: In one episode The Dragon Baron Ashura captured The Hero Kouji and Mazinger-Z and gave him the "join-us-or-die" choice. After the Kouji's predictable answer, Ashura sentenced him to death, and instead of shooting him, Ashura's Mooks started a bunch of giant power saws and drills to cut Mazinger-Z to pieces. To be fair, Kouji was inside Mazinger-Z and they could not get him out, so they could not just shoot him.
 * Madara from Naruto also seems to have a pretty bad case. He can become intangible at will, warp people into a pocket dimension, and can teleport himself (or others) wherever he likes, but when it's time to capture the protagonist, he'd much rather delegate the task to less capable subordinates or start a ninja war than simply use his own powers to easily capture the protagonist when he's asleep or off-guard.

Comedy

 * A recuring Mitchell and Webb sketch featuring the superhero characters BMX Bandit and Angel Summoner. The sketch would always begin with BMX Bandit outlining some overly complex plan, primarily involving BMX based stunts, to deal with the current problem, to which Angel Summoner would reply, "Or I could just summon a horde of angels to sort it all out."

Comics

 * Justified for the Joker, 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 out right, "Why Don't You Just Shoot Him?" (and may be the Trope Namer for the trope).
 * Batman villians have this like it's contagious. The Riddler, despite "going straight" for a while, 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.
 * When the entire Spider-Man Clone Saga in all of its insane permutations was finally revealed to have been masterminded by Norman Osborn (who had been faking his own death for years, to boot), for the simple purpose of driving Peter nuts.
 * Well, we can safely say that he succeeded in that...
 * In Superman's Pal Jimmy Olsen #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 murial 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 Super Dickery and treat Jimmy like crap without explaining why until Jimmy backs out of the trial.

Films
"Jason: You just asked for it?"
 * As the page quote implies, Yzma from the The Emperors New Groove (and the Spin-Off series The Emperors New School) has an affinity for making complex plans to destroy Kuzco, which of course never work. Kronk lampshades this at least once.
 * In the Tim Conway/Don Knotts movie The Private Eyes, 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 got brought up.
 * Austin Powers spoofs this trope as it commonly appears in spy films. Dr. Evil is notorious for making his plans to kill the titular character exceedingly complicated, such as in the first movie where he ties Austin and Vanessa to a pole 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 defeatable guard stationed there. Dr. Evil's son, Scott, is usually the one who calls him out on these things and states much easier ways to kill Austin.
 * In The Bourne Identity, 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.


 * The James Bond villains are bad enough to name a whole separate trope - for instance, instead of simply killing Bond they beat him up and leave him in a somewhat easily escapable cell, leave him in the middle of an alligator farm, and of course, shoot a mook that failed them instead.

Literature

 * Voldemort's biggest flaw (besides underestimating The Power of Love) is wanting everything he does to be as epic as possible, regardless of practicality. Take arguments pro and con elsewhere.
 * This kind of thing is parodied in Sluggy Freelance 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 Batman Gambit 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.
 * This seems to be the generally accepted MO for the Yendi in novels set in Dragaera.
 * A major aspect of the White Court of vampires in The Dresden Files 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 in a Xanatos Gambit is viewed with admiration. So, it's institutional Complexity Addiction.
 * Oddly enough, there's a practical reason behind this, making it a (somewhat) justified trope. White Court Vampires do this to limit their accountability and culpability for their actions, which is important, since 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.
 * In PG Wodehouse's Jeeves and Wooster 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 The Adventures of Huckleberry Finn might be the Ur Example. 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, just because that's how prisoners in the books he's read escape. He insists doing it the easy way "just ain't proper."
 * Tom Sawyer takes the whole thing to psychotic extremes, when he is in fact overjoyed to have taken a bullet during the escape, as it adds to the adventure. What's even BETTER, is that at the end of the failed escape, Tom reveals that Jim had been granted his freedom all along, and he had neglected to inform them of this so that he could conduct the whole escapade in the first place.
 * In the Miller's tale of The Canterbury Tales, 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 Older Than Steam.

Live Action TV
""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?""
 * Many of the killers on Monk and 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.
 * Shawn even Lampshades this in a recent episode...

""He'd get dizzy if he tried to walk in a straight line!""
 * One episode of Monk had the killer in a coma for a year while the thing happened. How did he do it? With a bomb that was stuck to the bottom of the mailbox with a special type of glue that would hold out for a year, meaning it would be delivered in a year, 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 the murderer.
 * The Master in Doctor Who, especially the Anthony Ainley incarnation. As the Rani once summed him up:


 * In Angel Jasmine's plan while possessing Cordelia gives the impression of being massively overcomplicated. 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 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.
 * This is Nate Ford's shtick in 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 sufficiently skilled that his plans usually work. This is helped by his 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 rigamarole 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.
 * Barney on How I Met Your Mother puts way too much thought and effort into just about everything. When he wants to see whether he or Ted is the better Casanova, 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 Gambits 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 had not 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.

Tabletop Games

 * Warhammer 40000: Tzeentch, being essentially a god of Magnificent Bastards, acts almost exclusively through Gambit Roulettes, 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.
 * Well, Tzeentch is the god of ambition. Actually winning, and thus having nothing more to strive for, would if anything be more devastating than Failure Is the Only Option.

Theater

 * Cleopatra from Antony and Cleopatra, 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. Some of his allies seriously complain about the over complexity, wanting to simply use brute force instead.

Video Games

 * Mephiles' plan from Sonic the Hedgehog 2006 could have ended so early if he just, but he had to overblow the whole plot, making the entire plan completely useless.
 * Or he could even have just.
 * Hell 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.
 * The Lich King in World of Warcraft has a truly epic case of this. He comes up with a plan to  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, you 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
 * Also worth noting from the above,  appears to be in the Lich King's subconscious. Meaning
 * Dwarf Fortress 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 ? Why use a few cage traps when you can build a pressurized-magma Wave Motion Gun? 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 gladiatorial combat and deranged death traps are extremely popular as well.
 * Any feature, intended or not, someone will find a way to weaponize. 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 come back as violently vengeful ghosts, which we can turn against our enemies! Or setting up an elaborate gate and lever system to keep both Noble politics interesting and the population of Carp well fed?
 * 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 lets use strengthened doors and an invasion from Hell to flush the fortress of pesky kobold thieves?
 * Another example from the Sonic the Hedgehog Universe is the Game Gear game Sonic Labyrinth a game where Sonic has to solve puzzle mazes by collecting 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 manual scenario Eggman snuck into Sonic's house while Sonic was sleeping and stole his Sneakers to send him on this crazy quest.
 * In Superman for the Nintendo 64, Lex Luthor captures Superman and puts him into a virtual reality environment, challenging him with tasks such as flying through rings. Given the quality of the game, he may have been going for a Fate Worse Than Death angle here.
 * Heroic example: Professor Layton, 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 Luke in the most confusing way possible. It's a good thing Luke is almost as good at deciphering messages as Layton.
 * FEAR has an example of an aversion in the NPC AI. The AI in the game was universally praised for being intelligent and tactical - it seemed capable of flanking the player and otherwise taking advantage of poor positions. In reality however all the AI knew how to do was move from cover to cover to avoid getting shot at by the player. It was the design and layout of the levels that created the illusion that they were attempting something intelligent.

Web Comics
"Antimony: I suppose this calls for... an even more convoluted scheme!"
 * Order of the Stick:
 * Nale has this as modus operandi, to the point where all his plans are regularly described as "needlessly complicated" by other characters. Case in point. Apparently, he inherited this from his mother (although she didn't rear him). Even his class (multiclass Fighter/Thief/Sorcerer specializing in enchantment spells) is pretty much the same as a Bard (his twin brother Elan's class) but more complicated.
 * Xykon is the opposite of this trope, having a 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 thousands upon thousands of Hobgoblin soldiers.
 * In Girl Genius 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. Just so. Similarly if you ask a Spark to make a coffee machine, you end up with this. Though to be fair, it does make perfect coffee.
 * Heck, you don't even have to ask! They're so obsessed with building or improving new and crazy machines just to make them more complex, some even work in their sleep
 * 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, all in order to toughen him up and sparking either red or black romantic feelings. 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.
 * In Gunnerkrigg Court as a result of her time in, Antimony developed a case of this.

Web Original
"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 Evil Overlord List, item #85:

Western Animation
"Number 2: I'll be blunt. Your web page has stumbled upon our secret plan. Homer: That's impossible. All my stories are bullplop. 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."
 * In the theatrical Recess: School's Out film, the Mad Scientist character builds a tractor beam in order to move the moon. His evil plan goes something like this:
 * 1) Use a tractor beam to move the moon.
 * 2) This will change the seasons, making it winter all year long.
 * 3) With summer gone, schools will eliminate summer vacation.
 * 4) Children will spend more time in class, becoming better-testing students.
 * 5) 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, there are just so many things wrong with that plan that it wraps past funny and goes into tragic. The first step alone would have catastrophic consequences.
 * TJ flat out tells the villain that removing summer won't remove summer vacation, but the Big Bad just replies, "I can try."
 * The Simpsons' "The Computer Wore Menace Shoes" (during a parody of The Prisoner):

"Cecil: At last, I'm going to succeed where my brother failed in killing Bart Simpson! Bart: By throwing me off a dam? Isn't that a little crude for a genius like you? Cecil: You know, you're right. If anyone asks, I'll lie!"
 * Subverted in another episode when Sideshow Bob's brother Cecil is about to kill Bart by throwing him off a hydroelectric dam:

"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."
 * In an episode of 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 Thanksgiving Day 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 Thanksgiving Day never happens, and therefore the Thanksgiving Day Parade will not exist to keep him from crossing the street. He opted to try to alter centuries of history, possibly creating a Butterfly Effect that would cause the city he wanted to conquer to never exist in the first place, just to remove a temporary traffic obstacle.
 * Perennial Hanna-Barbera villain Dick Dastardly is the king of this trope. In his first appearance on Wacky Races 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.
 * 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.
 * The character on which Dastardly is based, Professor Fate from The Great Race, is almost certainly also where he gets this tendency; Fate spends the entire race cheating, much like Dastardly, 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) probably matches how Dastardly would think, as well. Fate celebrates the victory for a moment, then lapses into a huge tantrum because, even though he wanted to win, he wanted it on his terms (which meant that he wanted to win 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.
 * Also The Perils Of Penolope Pitstop kept seeing the titular character getting captured and put into overly rediculous 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 The Amazing Chan and The Chan Clan, 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 Played for Laughs.
 * On Phineas and Ferb, 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. Of course, it's often lampshaded.
 * Arguably, Phineas and Ferb are prone to this as well. For example, in "Picture This", Ferb has left his skateboard in England:

"Ferb: ''"
 * For Phineas and Ferb, it's literally an addiction—Phineas goes into withdrawal when they're forced to climb a mountain the normal way, with no inventions. Ferb holds up a little better, but that doesn't mean he likes it.

"Shego: OK, let's get this Operation Too-Complicated-To-Actually-Work started!"
 * Most Scooby Doo villains succumb to this, and 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.
 * The best example of this is probably the Scooby Doo Mystery Incorporated episode "Mystery Solvers Club State Finals": the villain (revealed to be  , of all people), goes into excruciating detail about how he carried out his plot, which turns out to be an overly-complicated way of . This could be justified by the fact that the whole episode is just a fever dream Scooby's having, but still...
 * Strike that—the best example is from the following episode, where the Villain of the Week's plan is even more complicated, and even more pointless. The Gang lampshades this.
 * Note that 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.
 * Dr. Drakken from Kim Possible suffers from this. His sidekick, Only Sane Woman Shego, lampshades this repeatedly.

": You're not in any position to be calling the shots Steven; I'm the one holding the gun. Steve: Sure, you could kill me with your gun... but are you willing to try something much more elaborate and unnecessary?"
 * American Dad has this down to the Gary Oldman accent:

"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?"
 * Dr. Two Brains from Word Girl 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 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.

Real Life

 * Apparently this occurs in Real Life in not necessarily evil endeavours. There is even a rule called the KISS Principle: Keep It Simple, Stupid.
 * One notable situation is any sort of technical profession such as software engineering and other types of system design. It can be amazingly easy to over-optimize or overly-design complex systems when the end user/end result would never be able to tell the difference (and there is no difference internally other than personal satisfaction).
 * A common failure of military planning throughout history. If you have the option to use a sledgehammer and win, or to construct elaborate plans that will achieve the same results, you should use the sledgehammer. It's safer.
 * Study the planning of the Imperial Japanese Navy in WW 2, especially at Midway, but pretty much any operational plan they put out. Marvel at the widely spread, mutually unsupporting 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.
 * So we could say that their strategical overthinking resulted in their navy's... oversinking.
 * Most Conspiracy Theorists refuse to state any comprehensive theory in full, since they are almost inevitably laughably complex and likely to fail. Take this summary of the most common 9/11 myths. Please note that since that was posted, the Truthers' theories have actually gotten somewhat more complex.
 * It's been theorized that there's a psychological reason for the conspiracies. The human mind does not like to accept the fact that large scale atrocities can be achieved by simple means. For example, there's no way the president of the United States could have possibly been killed by just a guy with a rifle on the the roof of a building—never mind that the President is still just...a guy...