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"Just Exactly as planned": Light Yagami from Death Note, as a convoluted roulette finally pays off.
"Ha, loser. A true tactician doesn't know WHAT the hell he's doing until he's halfway done with it."

In a Xanatos Gambit, an especially cunning villain is able to trick the heroes into giving him what he wants. The Xanatos Roulette takes this one step too far. The villain is upgraded from "cunning" to "seemingly omniscient". The plan is ridiculously convoluted, often relying on events that are completely within the realm of chance -- yet it comes off without a single hitch (or so we're told; it's only in retrospect that we find out that pretty much everything that's happened in the series up to this point was part of one huge, overarching plot).

Basically, an attempt to make a villain seem impressive, stretched to the point where Willing Suspension Of Disbelief is broken. You really have to establish a character as The Chessmaster for them to be able to pull this off without arousing your audience's skepticism.

Often part of retconning in a new Big Bad, as it turns out everything up to then (including the supposed successes of the heroes against the old villains) is all part of their scheme. Also often the justification of the Omniscient Morality License; their control over events is supposedly total. Additionally, if a character messes with their own mind, getting their memories back almost inevitably becomes a Xanatos Roulette at some point.

May be parodied by having events obviously (and blatantly) be out of the character's control, and yet still have them take credit for it. Or, y'know, have the Xanatos Gilligan topple their Rube Goldberg plot with a poke.

Useful litmus test for distinguishing a Xanatos Gambit from a Roulette: If your first reaction on hearing the plan explained is "Dear God, that's brilliant!" it's a Gambit. On the other hand, if you inadvertently burst out "There is no way you planned that!" it's a Roulette.

When the main story is several of these folding out at once, you have a Thirty Xanatos Pileup.
Examples:

Live Action TV
  • Many of the terrorist plans on 24 are of this nature. For example, one plan in the fourth season involves kidnapping the Secretary of Defense, and threatening to execute him live on the Internet; using the traffic that generates as a mask for them hacking into every nuclear power plant in America; using that as a diversion for hijacking a fighter plane to shoot down Air Force One, then stealing the nuclear "football" from the wreckage; using the data in the football to intercept a nuclear missile being transported through Iowa; and finally, firing the missile at Los Angeles. The villains have no explicable way of knowing that the football would survive the impact, that the plane would crash close enough to their location for them to reach it before emergency crews, or that a nuclear missile would be on the road in the vicinity of their secondary team.
  • Subverted in Heroes: it appears the mysterious organization seems to be manipulating a ridiculous number of variables to come out at a dark future, but we eventually discover that things didn't turn out quite as they planned either...
    • Also, they specifically have a guy who can see visions of the future. Not to mention a little girl who can tell them exactly where any human being in the world is at all times. And a super-powerful telepath capable of reading people's minds over long distances and probing their deepest memories. And, initially, an agent capable of total *mind control*, being able to tell anyone she can talk to to do anything she wants them to do and then make them forget about it. All this makes the villains' prescience at least a *bit* more plausible.
      • Really, the dizzying array of assets the Company has at the outset of the series tends to make their *failures* less believable than their successes. As is frequently said about the RPG Exalted, with characters this powerful, if they haven't remade the world in their image by the end of the campaign, you must be doing something wrong.
  • An episode of Numb3rs centers around a dirty bomb threat somewhere in LA, which turns out to be fake; the actual point of the threat was to trigger the evacuation of the immediate area, so the crooks could break into a vault without interference. However, the plan requires that the FBI evacuate the right area, which was not revealed by the "terrorists" and which is only determined at the last minute through extreme deductive skill (and nearly incorrectly anyway). Had the FBI guessed wrong, the plan would have failed.
  • Parodied neatly in the Doctor Who Comic Relief spoof, The Curse Of Fatal Death. The joke here is that the unexpected roulettes become so expected that it is funny when they stop happening.
    • The basic idea is that each is using his time machine to bribe an architect to set a trap, or UNSET a trap. It is up on youtube, but unfortunately a direct link would result in them taking it down.
  • In Angel, Jasmine claims that virtually everything that's happened in the series up to the point of her arrival on Earth was the result of her manipulation. She may have just been trying to be impressive, though.
  • The main antagonist of the seventh season of CSI pulled this one off; she somehow managed to pinpoint the exact position a cat would die in a month ahead of time, among other things.
    • Actually, all the character had to do was know where the cat slept, or alternatively killed the cat directly herself.
  • In an episode of Scrubs, JD and Elliot are "even" after a series of events that would take too long to explain, and start to argue over whether they still are after he steals her Heterosexual Life Partner Molly. With the two of them having set up a "romantic evening," he accidentally crashes his scooter headlong into the hospital wall; hitches a ride with the janitor, who, being the janitor, takes him into the desert; gets Turk and Carla to pick him up, only for her to leave them both behind when Turk says he'd sleep with Molly; and runs all the way to her apartment, only to find her leaving, with a note that reads "now we're even." Cut to the all-powerful Elliot laughing herself silly.
  • Benjamin Linus from Lost may be one of the all-time greatest chessmasters. When he is introduced in season 2, an extremely elaborate plan to free himself and take some captives while getting rid of one they already had goes off without a hitch. (This plan, to put it in perspective, involves an assassination, catching himself in a net, and getting the father of a child he had already kidnapped to kill two of his friends. This is without counting the fact that he talked his way out of getting shot on numerous occasions.) In season 3, he steps it up a notch by somehow managing to force Jack to perform an operation on his spinal column. This may be one of the only times where Ben's plans don't work too well, as Jack slits his kidney as a level to force the Others to allow Kate and Sawyer to go free. Ben survives, and seemingly without doing anything at all manages to destroy several chances for survivors to escape the island, thanks to John Locke. He is also revealed to have orchestrated the destruction of at least 40 people in what is known as "the purge". By season 4, it is absolutely impossible to tell what he's planned and what he hasn't, especially the people on the freighter, who claim they are there solely to find him.
    • This was even more impressive back in Season 2, when it was still believed that the Others were a type of "sticks and grass" civilization of savages.
  • Many of the schemes in Veronica Mars verge into this territory, most notably the plan to kidnap her boyfriend's baby, which had as linchpins one character opening a letter addressed to someone else, her phone being tapped, and the sheriff driving all the way to Mexico without looking in his trunk.
  • Mission Impossible did this weekly for years.

Anime
  • In Bleach, much of Sôsuke Aizen's ridiculously longwinded plan relies on this. To be fair, though, it is shown many times that he had a whole string of backup plans. He switched to them one by one as Ichigo and company increasingly upset the normal functioning of Soul Society, until he finally resorted to walking up to them and taking the MacGuffin. It was probably his original plan not to be discovered until much later. Also, he was actually pretty much omniscient up until the entry of the ryoka, given that he had the entire Gotei command under mass hypnosis and all.
  • Yuuko of xxxHolic and Tsubasa Reservoir Chronicle seems to be aware of all "effects" to all "costs" via Wishes and manipulates them together to affect the future in ways mere mortals can't possibly predict. Things get complicated when the villain of Tsubasa Reservoir Chronicle does this too, often with the same costs and effects. Yuuko's one limitation is that only other people can initiate Wishes, and she has to be a Literal Genie to get the result she wants.
  • Death Note: Three words: 'Just as planned' (or "exactly as planned" if you go by the official translations). Actually, the entire series is a giant chain of interlocking Xanatos Roulettes; one of the main attractions of the series is watching them unfold and, occasionally, crash into each other. A lot of them don't really make much sense and only work because characters seem to forget what happened several episodes ago and take supernatural weirdness and freak occurrences at face falue, but don't pay much attention to basic forensic evidence.
  • Dartz, the leader of the Doma Organization in Yu-Gi-Oh, used this to recruit his followers; except for Mai, Haga, and Ryuzaki, all of his servants' past troubles that eventually lead to their joining the Organization were orchestrated by Dartz himself just so he could inflict a rage against humanity in them and use More Than Mind Control to cajole them into signing up.
    • Furthermore, in just about every duel in the series, the opposing duelist is always thought to be a Chessmaster, no matter how competent (or not) the duelist actually is. If I had a nickel for every time a duelist said says something to the effect of "he was planning it from the start!" (with the only logical exception being Atemu / Yami Yugi because he can control destiny with his will), I'd be a very rich contributor.
  • Digimon: In season two, each villain appeared (and sometimes believed himself/herself) to be the Big Bad, only for it to turn out that another, higher villain had orchestrated everything from behind the scenes. It all leads to one ultra-Big Bad having used people to use other people to use still others, with no one Fake Boss aware of the next one's influence. The most wallbanging-inducing aspect of this was the one villain who did know she wasn't the top dog: her arc was about her plan to destroy seven Cosmic Keystones and cause The End Of The World As We Know It, which would have made it impossible for her boss to get what it turns out he wanted (not to mention leaving him slightly dead.) Somehow it's doubtful that this is what he had in mind, and the same goes for *his* boss, who wanted to Take Over The World, not destroy it and all others wholesale.
  • In the anime and manga Spiral: Suiri no Kizuna, the ability to ravel and unravel Xanatos Gambits and Roulettes is, although it's not stated quite so baldly, a superpower many characters possess. Most of them assert that everything in the plot is a giant Roulette planned by the protagonist's older brother.
  • In an episode of Galaxy Angel, one (fake) debt leads to the faking of a kidnapping plot by Ranpha and Mint - which leads to another fake kidnapping plot by Volcott - which leads to another fake kidnapping plot by his commander - which leads to that victim's family landing another fake plot - which somehow results in some random little girl and bear faking one... Which results in the original perpetrator falling ploy to the plot, leading him to increase the random on his plot. The story ends on an infinite loop, of course.
  • The titular character in the manga/anime Akagi used a Xanatos Roulette on the blind player Ishikawa that came out of nowhere so fast, that despite everything adding up, it is still hard to believe that everything was on purpose, especially considering his inner thoughts seemed rather random during the match.
  • The Fullmetal Alchemist manga revealed that every single military action since Amestris's founding was orchestrated by Father, who was using his Homunculi to move the army and gain land until Amestris was large enough to turn into a giant Transmutation Circle. This one's so insane it goes right back to brilliant again.

Comic Books
  • Christopher Priest's portrayal of the Marvel Universe superhero T'Challa the Black Panther resorted to this trope several times during the course of his solo series.
  • In the series Daredevil, Vanessa Fisk was the Chessmaster behind the sinister events that transpired within the first two arcs of writer Ed Brubaker's current run on the title. Every player acted and every scenario unfolded with near-perfect precision, the one hitch being the confrontation with Matt Murdock occuring earlier than planned.
  • In the original V for Vendetta, the hero seems to imply that he killed a man, knowing that this would drive his wife to assassinate Mr. Susan. Made bearable by the fact that V never brags about doing this explicitly, but rather only hints at it. Discussion here

Film
  • The main villain of Saw is the textbook writer on this. Not only does he manage to contrive up elaborate traps (some of which can easily be thwarted in the end), but he also can somehow pick out the best people to inflict these on, and figure out exactly how they're going to reach to further his aims. And his does this all the while being bedridden.
    • This Troper has great fun spotting the obvious escape route of the traps in these films- and was greatly saddened by the 'impossible' ones in the later installments.
  • Subverted in the Ocean's Eleven series. The plans of the main characters match this trope quite well, apparently requiring everything to interlock absolutely perfectly. However, they have to adjust the plans several times due to unexpected variables.
    • However, the heist in Ocean's Thirteen relies on a Xanatos Roulette within a Xanatos Roulette, with a third Xanatos Roulette thrown in for good measure. By the end of the film, the plan becomes so circuitous that it almost qualifies as a subversion itself.
  • In Wild Things, Suzie plots to kill the dirty cop who killed her ex-boyfriend. She does this by entering into a conspiracy with an heiress and a guidance counsellor, that both girls will cry rape against him, but Suzie will recant on the stand, opening up the heiress to a multimillion-dollar lawsuit, to be paid by her mother and split between the three of them. With this plan complete, the guidance counsellor approaches the dirty cop at Suzie's suggestion, giving him a plan to kill Suzie, frame the heiress, and split the money between the two of them, but the guidance counsellor only faked Suzie's death, giving the two of them the chance to kill the cop; Suzie then betrays the guidance counsellor and, presumed dead, gets away with the money. And as if that's not enough, in the final scene, the defense lawyer from the rape trial, chosen from the phonebook, implies that he was somehow in on it all along.
  • The Game. Although it's implied at the end that they had backup plans here and there, not to mention a detailed psych profile on Nicholas to figure out exactly how he'd react, it's hard to believe that CRS could control every detail so completely.
  • The terrorist plot in Die Hard 2 depends on a conveniently-timed severe (but not too severe!) snow storm on the day their leader was being transported. Perhaps there was a deleted scene featuring a weather machine.
  • Subverted in Mystery Men in an exchange between Captain Amazing and Casanova Frankenstein that culminates with "I only knew that you'd know that I knew. Did you know that?"
  • The movie Total Recall, the main character (played by Arnold Schwarzenegger) is on earth, when he discovers he's a secret agent, who has to go to Mars, so that he can contact the leaders of the rebellion, but ends up accidentally betraying them. When he meets the Big Bad, played by Ronny Cox, he lampshades the impossibility of everything happening exactly perfect.
  • Eisenheim's plan in The Illusionist to fake his love's death and blame it on the Crown Prince of Austria has too many elements to have been coordinated and pulled off as masterfully as it was.
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  • The main villain, whatever his real name may have been, in Swordfish. More identities, schemes and deceptions than you can shake a stick at; neither the characters or the viewer are informed much regarding his real plans.
  • In Men In Black II, it is revealed that 25 years ago, "Kay" wiped his own memory but left himself a convoluted series of clues to follow. The whole plan would have fallen apart if a particular video store, diner, or bus terminal had been torn down in the last two decades, or if Agent Jay hadn't forcefully pulled him out of retirement.
  • The entire plot of Fracture requires that the correct cop be called into the scene of a murder, recognize the victim as the women he was having an affair with, and then attack her husband. Furthermore, it required that he not kill her husband, but be sufficiently angry to not notice that the husband was switching their guns. In spite of his otherwise brilliant planning, the husband failed to even realize that shooting someone, being found innocent of attempted murder, and then having life support withdrawn, constitutes a count of murder totally seperate from the initial crime.

Literature
  • Many of the elements of Smerdyakov's plan to kill Fyodor Karamazov in The Brothers Karamazov were obviously beyond his control. The book offers a good example of a Chessmaster attempting to manipulate events and people he realistically doesn't understand fully. The kicker though? He still pulls it off with a bit of improvisation.
  • The Count Of Monte Cristo has the Count executing a plan for revenge that's unspeakably convoluted. It would take a near-miracle -- or the Count's sheer charisma -- not to botch at several key points in the plan. Moreover, he is helped by his enemies having accumulated a number of skeletons in their closets in the intervening years. This is one of The Oldest Ones In The Book.
    • Similarly, Gankutsuou, an anime based off the book.
  • Used more realistically in Evil Genius, a young adult novel by Catherine Jinks. Although the hero, Cadel, is very good at manipulating people, when he attempts a Xanatos Roulette, it gets out of his control very quickly, leading to the death of several characters.
  • The Shadow Lord in the Deltora books made it clear: "I have many plans. Plans within plans..." And indeed, by the beginning of the series, he had them set in place so that he was prepared for any conceivable contingency. Except dragons.
  • In Harry Potter and the Deathly Hallows, it is revealed near the end that almost every major event that has taken place in Harry's life since about the halfway point of The Half-Blood Prince (in other words, for about a year and a half) was orchestrated or manipulated by Snape and Dumbledore, with the ultimate purpose of Voldemort's destruction. The reason they never told Harry any of this is because the plan involved Harry's supposed death, and it was vitally important he face it without any fear or doubt, and then discover it to be fake.
  • While we're on the subject of Harry Potter, the plot to get Harry kidnapped in Harry Potter and the Goblet of Fire is ludicrously convoluted. Basically, the villains want Harry to touch an object which will teleport him to their presence. Any object whatsoever could have been so enchanted. So instead of enchanting a teaspoon and sending it to him for a birthday present, they capture a (presumably well-guarded) trophy, arrange through convoluted means for Harry to enter the tournament for which said trophy is a prize, in spite of the fact that he's underage and shouldn't be allowed to enter anyway, arrange for him to win said tournament, in spite of the fact that the other competitors, being older, are generally substantially more competent than he is, and even then, the plan actually succeeds only by the most incredible luck.
    • This troper- being a diehard Harry Potter fan- would like to point out that a lot of the simpler plans wouldn't have worked thanks to the wards against various types of magical transportation that protect Hogwarts and most of it's grounds. Admittedly, the plan didn't need to be quite THAT complicated.
      • The critical element that makes this plan at least *kind* of make sense is that the Triwizard Cup is such a valuable and prestigious artifact that it's the one thing even Dumbledore wouldn't feel the need to run through some kind of security check to see if it's a Portkey. Of course, this doesn't really make sense -- for something as high-profile as this, wouldn't an at least routine check be necessary? -- and, more importantly, this is never stated outright in the books itself -- it comes entirely from Fan Wank and eventual Word Of God from J.K. Rowling.
  • In the Young Bond book Double or Die, a teacher at Eton is kidnapped and only has enough time to send a letter confirming his resignation and send his last crossword to 'The Times'. In this, he manages to get clues to Bond and his friends about what's really happened to him, where they can go to find more information and that a friend of his is coming to Eton. This teacher probably attended a school where Light was the headmaster and Jigsaw was the art teacher.
  • Successfully executed by The Chessmaster of The Assassins Of Tamurin, but without pushing Willing Suspension Of Disbelief, due to the years of effort she puts into it and the fact that she's crazy.
  • Plans within someone else's plans within your own plans within Children of Dune. Leto fakes his death in order to seek that last vision his father had (before also faking his death), only to be anticipated by his grandmother who insisted on having him tested for the signs of ancestral possession (through overdose on the one thing which will will cause him to be, of all things), which was also anticipated by his already-possessed aunt (by having an agent set to kill Leto [regardless if he passed or failed his grandmother's "education"] pointing out the alleged "instructions" from the grandmother being perfectly forged by the aunt) which was again anticipated by Leto by his timely symbiosis with the dominant species on Dune (sandtrout, which grow to sandworm), escaping his captors to meet with his father and onward into the fulfillment of his earliest prescient dreams culminating into the death of his aunt, the death of his father, the loss of his humanity and total control over the universe, its future and beyond. ALL the books from the original saga are in the more or less same vein.
  • And Then There Were None by Agatha Christie involves a terminally ill judge who not only wants to kill 10 people who got away with a crime, but to do it in a certain order ( From least horrible crimes to most horrible.), and to make the deaths fit a silly nursery rhyme that he happened to like. So many things had to have gone right ( If Vera Claythorne did not die last, or if she shot rather than hung herself, or if someone had seen Wargrave after his "death", or if Wargrave's psychological warfare on Claythorne didn't work and she did not commit suicide, or if Armstrong was less gullible then Wargrave thought, or if a sea storm had not sprung up, preventing any rescuer from reaching Indian Island, or if Wargrave's body had not rotted enough for the time of death to be uncertain, etc.) that it was almost impossible for everything to work. With the occasional plothole ( Lombard's gun was handled by Lombard, but only Claythorne's fingerprints were on it. Also, the police did not notice the nursery rhyme written on one of the walls, which pointed out how Armstrong died.), added into it, it all makes this one of the most silly Xanatos Roulette this troper has ever seen.
    • The Film Of The Book does away with the silliness with the result that Wargrave's plan ultimately fails, and Claythorne and Lombard survive.
    • After the Funeral is much in the same vein. Miss Gilchrist's entire plot to steal Cora's Vermeer painting hinged on every single member of the family not recognizing their own aunt at Richard Abernethie's funeral and believing that Richard had indeed been murdered. Even when one takes into account that none of the family members had seen their aunt in a long time, it still doesn't explain why they didn't notice that Miss Gilchrist - with whom they spent several days in the same house - looked almost exactly like the 'Aunt Cora' they had recently seen at the funeral. It also stands to reason that after Cora's death (the real Cora, that is), one of the family members would have to identify the body at the morgue, where the deception would thus be exposed regardless. Miss Gilchrist's plan to poison herself so as to appear innocent could also have colossally backfired.
  • Executed almost unwittingly by Cassie in the final Animorphs books when she surrenders the morphing cube to the Yeerks, depriving the Animorphs of their biggest advantage. End result: A whole bunch of Taxxons see what it can do, get frustrated with the fact that Visser One will never let them use it, and team up with the good guys so that they can undergo voluntary Mode Lock and escape their eternal inexpressible hunger.
    • Even more importantly the morphing power gives the Yeerks the ability to overcome their own nature as parasites, negating their need to go about enslaving other races in the first place, and eventually leading them to make peace with their long time enemies, the Andalites, and the rest of the galaxy.
  • The book Small Favor from The Dresden Files features a subversion. Harry considers the enemy's plot to be so complex it simply should not be possible, until Murphy points out that Harry really IS that predictable, and that the villains stood to gain by doing what they are doing, whether or not Harry acted as planned.
  • One fan interpretation of the Star Wars Expanded Universe is based on the idea that The Empire was instituted because Palpatine knew the Yuuzhan Vong were going to invade.
    • This troper has heard that it was one of the Sith in the Knights of the Old Republic that foresaw the Yuuzang Vong threat.
      • That is somewhat accurate, Koto R II explicity says that Reven forsaw the invasion of something called "true sith" and saw a hardened Sith empire as standing a better chance then the republic would when they invaded

Western Animation
  • Futurama parodies this in its (at the time) final episode -- the Robot Devil brags that his "ridiculously circuitous plan is one-quarter complete".
  • Parodied in The Aqua Teen Hunger Force Colon Movie Film For Theatres; antagonist Walter Mellon reveals that he created the Aqua Teens, Dr. Weird, and the Insanoflex so that Frylock and Dr. Weird would ultimately become enemies and fight to their deaths, whereupon he would inherit their houses and use the land to build a gym. Frylock then informs Mellon that they rent.
  • The Pixies' "thirty-seven year plan to take over Fairy World" in the Musical Episode of The Fairly Oddparents is so hilariously convoluted it possibly defies description. After it ultimately fails (for apparently not the first time), they wonder if they should try a six-week plan this time.
  • Homer Simpson's mother plotted to destroy a missile silo owned by Mr. Burns. This plot relied entirely on her dying at exactly the right time, Homer finding her video will on the right day, everyone using what they left her in precisely the right way (and Lisa stealing her crystal earrings), and Mr. Burns leaving a cinder block and chain near the cell Homer was trapped in.

Video Games
  • In the Marathon games, AIs who have gone Rampant tend to make these kind of plans.
  • City Of Heroes has a Doctor Doom-esque villain named Nemesis who takes this to an extreme in almost every encounter. In a single story arc, he tricks the hero into defeating some neo-fascists that looked like they were going to take over his infrastructure, just to save himself the bother; predicts that your contact will believe Nemesis' real plan was to take over the neo-fascists' robot army and send you to prevent that, while he proceeds with a kidnapping; and wraps it all up by having you supposedly kill him - even though, as a superhero, you may have never killed anyone else before (and indeed are explicitly prevented from doing so by the game mechanics), and despite his well-known use of countless robot doubles. Your Contact actually comments on this, noting that his death should have been impossible, speculating that Nemesis's real objectives were twofold, first to throw the heroes off his trail by faking his death, giving him breathing room to implement more plots, and second and most importantly, to get ahold of the technology from the kidnapped person to enable him to create perfect mechanical duplicates of his own mind, resulting in the annoying prospect of having to deal with an endless supply of super-intelligent mechanical jackass villains. Finally, many heroes might have preferred Nemesis's power-base to be taken over by virtually anyone that wasn't quite so good with the Xanatos Roulette. (It should be noted that this is far from Nemesis's most convoluted scheme. This editor cannot even remember all the details of many of them.)
    • Oh, it gets better when you find out that he engineered the Rikti war.
    • Apparently, he invented time travel as well. Still, his Paper Thin Disguise leads to some doubt: Nemesis never moves that openly. So, is he genuinely apologetic for unleashing The End Of The World As We Know It or is this a part of an even more elaborate scheme? Perhaps more importantly, how do I know I'm not a Nemesis Automaton? How do you? In one enjoyable villain arc, he does briefly convince you that you actually are.
  • The Metal Gear series is rife with Xanatos Roulettes, but Metal Gear Solid 2 takes the cake, though, with a plot so staggeringly convoluted that the bad guys reveal they didn't really have a goal. It was a test run to see how good they were at manipulating events. Surprisingly the bad guys are still in control long after they reveal their plot. Only the previous game's player character and his dead brother's arm have any freedom. It's a symbolism thing, honest.
  • Bian Zoldark from Super Robot Wars: Original Generation tried this. It was subverted by the fact that he was able to do it while still in control of his organization, but once he died as part of his master scheme, his own group fell to factional in-fighting and nearly doomed it.
  • In Super Paper Mario for the Nintendo Wii, the real final boss Dimentio has been orchestrating events all along as part of the Quirky Miniboss Squad so that after the hero's prophesied defeat of the Big Bad Count Bleck, he could take over the world destroying power, channel it through one of the heroes, Luigi, and destroy and recreate the universe. This plan is so complex it involves sending the heroes to hell (or ending their game in the Never Say Die terminology) so they can meet up with one of the future party members to fulfill the prophecy to defeat Bleck. How he knew they'd be able to leave the afterlife is not explained.
    • Actually, everything was foretold by the Dark Prognosticus, so Dimentio knew everything that was going to happen.
  • In Chrono Cross the entire plot is the result of multiple sides manipulating each other into doing their bidding. But it turns out, the manipulators are also being manipulated. And so are the manipulators of the manipulators. Now throw in Time Travel and AlternateUniverses and you see how overcomplicated this actually gets.
  • In Command & Conquer 3, Kane initiates a massive world war with the express intention of provoking GDI to utilize their Ion Cannon on the Temple Prime, detonating a Liquid Tiberium reserve hidden underneath the Temple. This was done in order to lure the Scrin to Earth, so that Kane could capture one of their Threshold Assembly towers to gain access to their technology. There are a number of events that take place during the game that actually threaten Kane's Xanatos Roulette, and much of the Nod player's missions involve fixing these things so that Kane's plan actually works.
  • The entire underlying plot behind Fire Emblem: Path of Radiance is a twenty-something year-old Xanatos Roulette centered around Lehran's Medallion and channeling power into it by thrusting the entire continent into a war, so that Ashnard could release the Dark God.
    • And in the sequel, Radiant Dawn, it is revealed that Ashnard was but a pawn in an even larger roulette, orchestrated by none other than Lehran himself, who turned out to be Sephiran, the Prime Minister of Bengion, and a major ally in Path of Radiance. He wanted the "Dark God", Yune (who's actually rather nice, if a tad rude) to be released, only because this would also wake up her sister, Ashera, the Goddess of order, who would then cleanse the world of all life.
      • In addition, Ashnard's method of seizing the throne received a retcon into one of these. In Po R, it was assumed he had just killed everyone in his way, but in RD it's revealed that he had made his father sign a blood pact, then had it invoked to wipe out the entire royal family.
  • In Jade Empire, Master Sun Li, the Glorious Strategist, pulls off a twenty year Xanatos Roulette to put himself in power by training the main character so that only he knows how to kill him, yet keeping him loyal, letting him kill the emperor after baiting him to that point, and then killing the main character and taking the throne.
  • Onaga's manipulation of Shujinko to revive him in Mortal Kombat Deception can certainly qualify.

Web Animation
  • Parodied in the Homestar Runner toon DNA Evidence, wherein Strong Sad is "revealed" to have been at the root of an absurdly complicated chain of events.

Web Comics
  • At the end of the "Professor Madblood and the Doppelganger Gambit" arc in Narbonic, Helen claims the whole chaotic sequence of events was her plan. As the series goes on, it's hinted that she plans a great deal more than typically believed - Artie at one point suspects everything about him was engineered so that he could save Helen's life at one crucial, impossible-to-predict moment. Of course, Helen is a megalomaniac (albeit an extremely cute one), so some or all of this could be from her own self-aggrandizing.
  • From Daily Victim by Dave "Fargo" Kosak, the features "Okay man, listen up: I've developed a 32-step program designed to get my hot girlfriend into cosplay," where the focus character tries to get his girlfriend to like dressing up without realizing that she's being manipulated, and "My 6-month plan to get my hot girlfriend into cosplay has colossally backfired", where his plan has worked too well, and he needs to wean her off of her obsession via an equally circuitous scheme.
    • And then there's the system administrator who always has a backup plan: "You see, you never want to fake a major organ failure to hijack an ambulance to a concert where you falsify medical documents and sneak into the trunk of your friend's car in a Spider-Man costume unless you're PREPARED for the eventuality that someone might get hurt if the car slams into a deer."
  • Near the end of It's Walky, a We Can Rule Together speech by Penny and (presumably correct) extrapolation by Alan reveal that Dargon founded SEMME in the seventies specifically to gather abductees and Martian technology, the former to be given just this We Can Rule Together speech, the latter in anticipation of SEMME's eventual disbandment and the resultant scattering of Martian technology to military centers around the world. The latter event, by the way, was thirty years later and contingent on an HA caper they couldn't possibly have predicted, itself following his death and resurrection. If either Dargon or Penny had lived long enough, we might have seen what, exactly, they planned to do with the world's military infrastructure destroyed.
  • The entire Bird "conspiracy" in the webcomic Kevin And Kell. Too long to explain, but it implies giving somebody super powers, Time Travel, The Y2K bug, and locking an odd couple in a room.
  • Dominic Deegan, with his limited ability to see the future, plays The Chessmaster in almost every arc, manipulating events to a more ridiculous degree each time. By the Snowsong arc, he's stepped into Xanatos Roulette territory even considering his powers, albeit mitigated by some minor setbacks.
    • The mindgames the Travorias play on one another throughout the series would count as Xanatos Roulettes...except that they nearly always fail.

Tabletop Games
  • The chaos god Tzeentch, also known as the Architect of Fates and the Great Schemer, is the Warhammer and Warhammer 40K god of xanatos roulettes and literally lives for pulling the strings of reality in increasingly implausible and intricate ways -- in fact, because such scheming is such an intricate part of its being, Tzeentch is virtually incapable of doing things straight. Even the other gods step carefully around Tzeentch because of this, which is probably just what it planned anyhow.

Real Life
  • Religious bigot and all time champion nut-case Jack Chick believes that Satan is using the Catholic Church, the Jesuits, and the Alexandrian Bible to win the Muslims and the Russians to his side and claim victory at the Battle of Armageddon. He also claims that all of this is specifically mentioned in The Bible. Okay then...
  • Religious bigot and nutcase Pat Robertson attributes 9/11 to God utilizing Wahabbi Muslims to execute an attack on New York with commercial jetliners so as to deliver a message regarding his (God's) displeasure at American tolerance of homosexuality. Um...yeeeah.
  • The sheer number of Roulettes/Gambits attributed to "the Jews" (sometime encoded as "New York money men") simply boggles the mind.
  • The revenge of The 47 Ronin falls into this category due to the plot hinging on Lord Kira not dying from other circumstances in the interim.

Other
  • Spoofed in an episode of the Frantics' sketch comedy show Four on the Floor. Burglars are breaking into an office building. As they close in on the safe that is their target, the ringleader accurately predicts a series of improbable events including the night watchman having a fatal heart attack, a flying priest passing the office window, and a door-to-door dynamite salesman happening to be in the area. Each time, the leader smirks and tells his cohort, "Just like I planned it!"
  • On the Reunion episode that aired immediately after the final episode of Survivor: China, season winner Todd implied that everything that had happened during the show, up to and including who was selected to be on the show, was all somehow part of his master plan.
  • This troper believes that the purple and pink unicorns of the Charlie the Unicorn fame went through some pretty crazy convoluted schemes just to steal from Charlie. In Charlie the Unicorn 2, the fact that they get sucked into a strange vortex and find an amulet to return to the alleged “Bo-nana King”, have a somewhat gratuitous Spanish conversation to a giant block Z, ride a giant sneaker, arrive at the Temple of the Bananas, then perform in a sing-a-long accompanied with a chorus just to discover that Charlie was the Banana King all along is a completely outrageous chain of events seeing how this was just used to distract Charlie long enough to rob him of his valuables. Then again, the pink and purple unicorns could just be obfuscating stupidity…or are they?.
  • In an article on creatin villains, the sample villain, the Fire King, infiltrates an elven noble's household, takes over the household, becomes the king's trusted advisor, starts a war, eliminates elements on both sides to prevent peace. The point of all this is to wipe out all the elves so that he can peform a ritual to absorb all the magical energy in the world, and conquer hell.