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Aizen from Bleach 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.
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.
When she first used Resurrección, Harribel displayed the necessary speed and power necessary 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 water powers and his ice powers, evidently attempting to set up some sort of 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.
Mazinger Z: In episode 39 The Dragon Baron Ashura captured The Hero Kouji and Mazinger-Z and gave him the "join-us-or-die" choice. After 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 (it must be mentioned that Dr. Hell and Count Brocken were waching the scene and Brocken told he would just shoot him). To be fair, Kouji was inside Mazinger-Z and they could not get him out, so they could not just shoot him.
Obito from Naruto has 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, and has been capable of doing this for the past twenty years. At no point before the start of Shippuden did he ever consider capturing not only Naruto but any of the other eight demon hosts that are necessary for his plan. And even then, when he decides it's time, he sends in a bunch of far less capable subordinates or starts a ninja war rather than simply use his own powers to easily capture the hosts when they're asleep or off-guard. There is also the fact that he infiltrated his own organization by pretending to be a harmless fool for seemingly no reason.
Tobi's one saving grace is that he's following the directions of the real Madara. He doesn't really know how to plan, he's just doing the best that he can in the meantime.
Miki as The Bully and a Jerk with a Heart of Gold, displays this when at episode 3A when she insists on fighting the Worthy Opponent 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.
This blog argues that this was Mercurymon's Fatal Flaw in Digimon Frontier, 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".
Transformers Masterforce: Hydra. Oh, dear God Hydra. In a Henshin Hero 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.
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).
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-ManClone 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.
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 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.
Silver AgeSuperman had a severe Complexity Addiction, thanks to his story breaking power level. 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. Sure, Superman could just destroy the aliens - but that would take two pages.
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 Dark Avengers, 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 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 Marvel Comics pre-Annihilation cosmic narrative, whether they were Thanos, Adam Warlock, the Magus or the Goddess, used incredibly byzantine plans, often with a relatively mundane goal in mind (in The Infinity Gauntlet, for example, Warlock's strategy was aimed at getting Thanos to raise his hand at a specific moment so the Silver Surfer 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 The Avengers #169, multimillionaire Jason Beere learns he is dying, and out of It's All About Me 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 neutron bomb 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.
Lucius Malfoy in Child Of The Storm. While, as yet, he hasn't put a foot wrong, 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 the author. There is a reason that this fic has the single longest entry on the Gambit Pileup page, and the above could be a tacit acknowledgement of this by him.
Yzma: Ah, how shall I do it? Oooh, I know... I'll turn him into a flea; a haaarmless 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, (crazed laugh) I'LL SMASH IT WITH A HAMMER!
TJ flat out tells the villain that removing summer won't remove summer vacation, but the Big Bad just replies, "I can try."
Films — Live-Action
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 brought up. Then again, Lord Morley never could get anything right.
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.
Jason: You just asked for it?
Present in Captain America: The Winter Soldier with the HYDRA plan to assassinate Nick Fury. The Winter Soldier has a weapon capable of destroying the armoured car, his 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.
Word of God says that this is exactly Schultz's fatal flaw in Django Unchained, and he ends up getting killed because of it. It's amply demonstrated: He 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 the guy they're dealing with figures it out thanks to his Hypercompetent Sidekick 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.
Heroic example in 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 (and conspicuous) but functional one. Or just book passage on a transport, or 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.
Emperor Palpatine in Return of the Jedi develops a frankly ridiculous plan, 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 Palpy was more interested in getting Luke on-side than in actually winning the battle, and kept pursuing his overcomplicated plan even after it became apparent the Rebels were not playing ball.
Walter deliberately tries to avoid this during the "handoff" scene in The Big Lebowski, preferring to beat Bunny's location out of her kidnappers instead of paying them the demanded ransom. Turns out there is no handoff. The kidnappers want them to simply drop the money off. Walter doesn't take the news well.
In Now You See Me, 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 Jack Reacher, who explain it as "We make it messy now so it won't be messy later."
Back to the Future 3: In 1885, Buford Tannen thinks Doc Brown owes him $80, and plans to kill him on Monday if he doesn't pay up. Doc and Marty can't just use the time-traveling Delorean to escape because it's out of gas and can't accelerate to 88 miles per hour. So they come up with a complex scheme to hijack a steam locomotive, boost its engine power with chemically-infused logs, and use it to push the Delorean up to 88 mph across a bridge that hasn't been built yet into the future. It never occurs to them that it would be far simpler for Doc to just apologize to Buford and pay him the damn $80. Then Marty manages to defeat Buford and get him arrested, eliminating the threat to Doc . . . and they go through with the locomotive-hijacking plan anyway, even though it's now completely unnecessary.
Albeit slightly justified, as even if Doc Brown doesn't need escape, the plan is still needed to get Marty back to 1985.
Loki from Thor really enjoys jerking around the people nearby him but never stops to think if there's a better way to handle his schemes and ends up making mistakes that could be rectified if he'd just avoid doing certain things.
Mafia hitwoman Salino of The Sting is pretty much this trope (even when 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 Love Interest... 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 The Dark Knight Saga 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 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.
Harry Potter: Voldemort's biggest flaw (besides underestimating The Power of Love) is wanting everything he does to be as epic as possible, regardless of practicality. This is even noted in-canon.
It got ridiculous in Goblet of Fire, where he arranged everything so that Harry would be forced to participate in the Triwizard Tournament and rigged the events to help him become the champion, just so that he would touch the cup (which had been turned into a Portkey), and get teleported to a graveyard where Voldemort and Wormtail were waiting for him so that they could use his blood to restore Voldemort's body. All in spite of the fact that Harry was too young to participate and could have died (thus destroying any chances of Voldemort being able to get his blood, as well as the opportunity to have his revenge by killing him himself), or that (initially) Harry had no interest in taking part in the event, so for all Voldemort knew, the kid might not even have made an effort to win. And even if Harry hadn't died, someone else winning and touching the cup might have given away Voldie's plans, or at least exposed Barty Crouch Jr. And worst of all, Voldemort could have turned just about anything into the Portkey. And even more ridiculous, Voldemort explicitly said that any wizard who hated him would've made the potion work, he just wanted Harry Potter's blood. So really, the entire book's plot was all because of Voldemort's huge ego.
And then there's his refusal to use random objects as his horcruxes. Or store 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 said 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.
A more deliberate example would be Oliver Wood's various incredibly elaborate Quiddich play plans, which tend to take multiple diagrams to explain (with said diagrams already enchanted to have the lines move around).
This seems to be the generally accepted MO for the Yendi in novels set in Dragaera. For example, in the novel 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 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 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 The Plan 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.
Part of the reason for this behavior is that, although White Court vampires have Super Strength, Super Speed, a Healing Factor, More Than Mind Control capabilities and so on and so forth, they are still considered lightweights in the supernatural community. They can be dangerous in a fight, but are physically outclassed by many, many other creatures. So, they turn to The Plan to avoid any actual confrontation.
Further, it should be said some of them have no qualms admitting a human or wizard is a Worthy Opponent if they can successfully manipulate a White Court Noble into doing what they want.
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.
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.
The Assassin's Guild in 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 has no compunctions about fighting dirty.
In Somtow Sucharitkul'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 Ozma Of Oz (And the film adaption Return to Oz), 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 Batman Gambit in the Kim Newman short story "A Shambles in Belgravia", an Alternate History where Irene Adler approaches Professor Moriarty to steal some 'intimate' blackmail photographs of herself from the Ruritanian 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 Without Remorse. 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.
In Twilight, the Cullens end up with three 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 lookout, one of whom who could see the future and the other of whom could read minds, all against two vampires, with the third having defected), they decide to split themselves up so that Esme, Rosalie, Edward, Emmett, and Carlisle go on a wild goose hunt after one of the vampires while Alice and Jasper take Bella first to her home in Phoenix and then plan to take her to other major cities.
In Crescendo, all 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 "It Amused Me."
The 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.
Live Action TV
Burn Notice: 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, 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.
The Invisible Man: 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?
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.
"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?"
"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.
The Master in Doctor Who, especially the Anthony Ainley incarnation. As the Rani once summed him up:
"He'd get dizzy if he tried to walk in a straight line!"
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 plan to kill the Doctor seemed needlessly 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 52nd century.
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.
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 The 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.
And, the short-arc plan "The Robin," where he had to eliminate Robin's current boyfriend, enlist her office Frenemy, use a Batman Gambit 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: "Hope she says yes."
A minor plot point in the Season 2 finale of Sherlock: In an aversion of Hollywood Hacking, 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.
Morgana from Merlin has this to the point of Villain Ballnote See the recap of Castle of Fyrien for one. Best summed up by this quote from the TV Tropes Lancelot du Lac recap page. Oddly enough, in this episode it actually worked 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!
Some of the UnSubs of Criminal Minds 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 King Arthur-themed scavenger hunt to catch him and save his victim, who was also his daughter.
While the Goa'uld of Stargate SG-1 attempted to be this, they came off as just a bunch of Large Hams what were Too Dumb to Live. Ba'al, on the other hand, actually had this. In the DVD movie Stargate Continuum, 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.
A recurring 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."
Everyone in 'Allo 'Allo! 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.
MacGyver: 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 Why Don't Ya Just Shoot Him?.
In one episode of The Big Bang Theory, Sheldon develops a game of three person chess, then starts adding new pieces, and new abilities, and it quickly 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!
Agents of S.H.I.E.L.D.: Victoria Hand in "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 Gambit Roulette 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 the later episode "Turn, Turn, Turn", Hand reveals that she's been evaluating Coulson to determine whether he Came Back Wrong, so the events of "The Hub" might have been a Secret Test of Character (though still an overly complex one).
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".
Calvin and Hobbes: As members of the secret club "G.R.O.S.S." (Get Rid Of Slimy GirlS), Calvin and Hobbes often come up with schemes to annoy and/or terrorize their neighbor Susie. 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 with "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.
Warhammer 40,000: 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.
Infernal Exalted 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 D&D's Dragonlance and Spelljammer settings have this. It's most obvious in the inventions 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 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.)
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.
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.
The board game Mouse Trap, where the Rube-Goldberg mechanism for catching the mice was so complicated that it rarely if ever worked.
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 guarentee! It's the craziest trap you'll ever see.
Mephiles's plan from Sonic the Hedgehog (2006) could have ended so early if he just killed Elise, thereby releasing Iblis, but he had to overblow the whole plot, making the entire plan completely useless.
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, 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.
The Lich King in World of Warcraft has a truly epic case of this. He comes up with a plan to 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, 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 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 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, Arthas' intervention appears to be in the Lich King's subconscious. Meaning 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.
Dwarf Fortressplayers 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 into the bottomless pits of Hell? 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.
With any feature, intended ornot, 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 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 killer 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 — let's 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 collectingkeys. 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.
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.
Many of the murderers in Ace Attorney 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.
Apollo: I've seen Rube Goldberg machines that were less complicated.
This also applies to Manfred von Karma's revenge for 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 Disproportionate Retribution.
People who play Aurora live by this trope, with the game being so complex any lesser person will go mad from frustration.
General Viggo from Fur Fighters 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.
Gilgamesh in Fate/stay night 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 (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, even though he is by no means the strongest or most skilled.
He is repeatedly stated to be the strongest servant (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 Umineko: When They Cry 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.
There's one particular scenario in Ride To Hell Retribution 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 awful PS2 FPS game "Daemon Summoner" has a dreadful stealth level which requires you to sneak on board a ship, and despite said ship 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.
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. They're so obsessed with building or improving new and crazy machines just to make them more complex, some even work in their sleep.
In Gunnerkrigg Court as a result of her time in the forest, Antimony developed a case of this.
Antimony: I suppose this calls for... an even more convoluted scheme!
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 killing him when he fails, all in order to toughen him up and spark 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.
Rose tends to attribute to those around her a complicated motivation when a simpler one may be much more accurate, as well 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's just really overly affectionate and happens to have the same interests as Rose does.
Caliborn takes this Up to Eleven. 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 Rage Quit.
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. As seen above, he inherited this from his mother (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 class does serve an additional narrative purpose: it allows him to be Lawful (unlike Bards) and therefore be more of an evil opposite to his brother.
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 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.
That's not to say his plans are stupid by any means. By creatively using a single spell he managed to destroy a very large chunk of the Sapphire Guard who were guarding the throne room.
In Tales of the Questor, 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 Roommates are no better. For example a simple installment of the custody battle between the Erlkönig and his ex Jadis involved Blood Magic, Shadow Archetypes, a magical mercenary doppelgänger, a cursed ring, an elaborate Dream Within a DreamLotus-Eater Machine, wrapped in several layers of symbolism, including planting ideas hundreds of years before, etc.... they both have a terminal case. (They are also incredibly 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 flawsnote still having slightly pointed ears, a shadow that shows his true form, using "Figlio Perduto" as ringtone, going with the alias Lord ErrolKing, etc. which either means he is leaving clues so this trope, or the proof that he is reallybad at disguises.
Chaos in El Goonish Shive actually deliberately makes her plans unnecessarily complex, largely because the alternative is too boring for her.
Voldemort's tendency toward this kind of thing in Harry Potter 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.
xkcd brings in someone with one of these for "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 Concession it turns out that what Joel thought was a carefully planned out Xanatos Gambit, had too many loose ends. 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.
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 Doctor Horribles Sing Along Blog feels that "killing is beneath him", and, as a result, uses non-lethal weapons such as the freeze ray. At first, anyway...
Accord of 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 a twenty-three year plan to end world hunger.
Tom Collins in Demo Reel 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 Sanity Slippage and ends up with a beatdown from Rebecca, Donnie and Karl.
In Avatar: The Last Airbender, Evil Chancellor 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.
"The Computer Wore Menace Shoes" (during a parody of The Prisoner):
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.
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 stuffing ballots (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.
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 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 Penelope Pitstop 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 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.
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.
Ferb: If we hadn't been able to invent something soon, I was going to scream.
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.
In the Scooby-Doo! Mystery Incorporated episode "Mystery Solvers Club State Finals": the villain (revealed to be The Funky Phantom, of all people), goes into excruciating detail about how he carried out his plot, which turns out to be an overly-complicated way of getting rid of his team so he can stop being a sidekick. This could be justified by the fact that the whole episode is just a fever dream Scooby's having, but still...
In the following episode, the Villain of the Week'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, somethings 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.
Shego: OK, let's get Operation Too-Complicated-To-Actually-Work started!
The Affably Evil Señor Senior, Senior insists on sticking to code of classic villainy on principle, 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 an 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 masking as poor) that nearly succeeded. And when Kim was about to catch him his son Señor Senior, Junior succeeded with another simple plan: 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.
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 Rube Goldberg Device 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.
Dr. Two Brains from 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 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?
Batman: The Animated Series 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 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 Regular Show "Steak Me Amadeus", 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. Capicola Gang Leader: Well it worked didn't it?
Pretty much every plan come up with by the Legion of Doom in Challenge Of The Super Friends. This was probably due to there being thirteen members and wanting everyone to seem like a participating member.
In Wakfu, Qilby the Traitor tried to accomplish his goals with a rather complex plan that really wasn't necessary. Adamai even points out that 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 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 My Little Pony: Friendship Is Magic, 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, divide them with hedge walls, give them lectures on how how the elements they bear are either weaknesses or hyprocritical, THEN hypnotize them to make them unfriendly with one another.
Study the planning of the Imperial Japanese Navy in WW2, especially at Midway, but 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.
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.
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 a better tactical general than strategic general.
Tony Hawk mentioned in The Bones Brigade An Autobiography that he wanted to do as much tricky skateboard manoeuvres as he can, despite being criticised for it. The most prominent example being his evolution of his McTwist: First he done a McTwist, then moved on to one foot McTwist, then body varial McTwist, till it ended in an ollie McTwist, as in doing a McTwist with no hands grabbing the board!
The Toady One, maker of Dwarf Fortress, has said he wanted his game to simulate reality down to the quantum level. Fans told him that a game about mining and building would be fun and popular, as long as he threw in some basic graphics and simpler controls, but he demurred. Then Minecraft came out and became one of the most popular games of all time...
Many people claim that the U.S. Common Core school curriculum is this. Showing very complicated ways to solve extremely simple math problems, even taking up a full page to solve an addition problem. Even parents that have degrees in high level math have no clue how to solve simple problems the "Common Core" way. Probably best explained by this viral post.