I got creative and imagined how the "villainous enneagram" would be like, this is the fabulously ~evil~ result. I also attempted to find some good fictional examples - if you have other representatives, archetypes or more accurate ones, feel free to post them. I hope you like it (or find it vicious, in this case)!
Ronan The Accuser
Calm and collected rogue who is actually a brutal zealot. Will systematically destroy everyone on their crusade to be completely content - which will never be the case. Dangerous as they are convinced that they are not villains - the 1w9 thinks that what they do is actually right, necessary and good. Driven by a deep dissatisfaction. Annihilate everything they find unacceptable with their own system of justice, calling it a "sacred path of correction". Relies on ritualistic practice, has a church-like organization that backs them up. All of their allies and servants have to pass a rigorous testing program before they can join.
The influencer overlord. Their desire to reshape society is completely misguided - they make it their goal to brainwash billions of minions and enemies for their own good. Everyone is the same, throwing themselves on the ground before their master in perfected unison, chanting: "Our Jesus has arrived!". One of the most idealistic villains of the enneagram. Will condemn and wipe out everyone who does not love them. May forgive an enemy once... twice, even... but come for their neck the next time, killing them without visible remorse. Villain who can order around others the best. Obey or pay.
A charming villain of conviction with great stamina. Torments enemies because they are "heartless and flawed". Overprotective, holds you close until you suffocate - and it's your fault. Parental figure of their followers who are ardent and always say yes. Love is compulsory in their system - but not actual selfless love, just their version of it. Will convince everyone of their ideology by showing how much they "care" (=control). Will threaten to kill themselves should someone dare to challenge them. Even fellow villains believe that they are such a principled and righteous darling, which could not be further from the truth. They are consumed by resentment and a rigid will to puppeteer everybody. Favorite strategy: taking someone hostage.
Most manipulative, seductive villain. A brilliant and eager emotional strategist, and completely glamourous. Hides their uncompromising ambition behind kindness. Can get anyone to do what they want by making themselves a blank slate for all possible projections. Guilt trips entire institutions, no, nations (!) into submission and unconditional reverence. Knows exactly how to make their targets fall in love with them, since they can portray such a luscious dream. Strike once dependency is established. Distinguished by being able to create maximal attractiveness. Competitive in their evil Medusa/Adonis type of sexiness. Once enthralled and enslaved by the 2w3, there is no way back. Survivors of their treatment never fully recover emotionally.
Dazzling capitalist-exploiter-diva-in-chief. Utterly two-faced. Due to their excellent understanding of people and their wishes, they expertly "fake it until they make it" and then stab you in the back with the most charming, self-satisfied smile. On top of any villain hierarchy. Loved by friend and foe alike. They are so powerful since they understand the demands of their surroundings at an instinctual level. Their ability to persuade is almost innate. Master orator, has an elaborate program of propaganda that apparently caters to everyone's needs. Savior mentality. Comes as your greatest desire, leaves as your worst trauma. Switches between icy and compassionate. Portrays self as an admirable deity, makes you love it when they step on you. Knows how to get away with everything. Are terribly efficient and compelling without even trying.
Extreme hazard for society as they conceal their vain motives until it's too late. "The betrayal that is not seen is the worst" - That's the 3w4 villain in a nutshell. So apt at deception and creating an image that their rise to the top is almost inevitable. Their abuse tactics come out once they are in charge and everyone is powerless. Obliterates opponents by becoming their favorite person. Nothing's ever their fault. Tragic, narcissistic psychopath. If they have feelings, they are self-absorbed ones of agony- other than that, this villain is capable to set aside their emotions. Hence, they conduct the most gruelling missions that other enneagram villains would shy away from. Most professional rogue of the enneagram. Brag and sigh about how taxing it is to be so corrupt while sitting on their diamond throne, surrounded by slaves who serenade them.
The Phantom of the Opera
The worst villain of the enneagram. Outperforms every other evildoer out of sheer jealousy and ambition. Terrible emotional outbreaks. Operates behind the scenes and nobody knows. Are never who they seem to be. If blamed, they become the victim. Impersonates, schemes, tortures, kills their way to victory. May orchestrate a trap, illusion or an entire genocide. Aim to inflict their suffering onto others, and we all know that the 4w3's suffering is the greatest of all. Roleplays during torture, telling their victims not to be so sensitive since THEY are the ones who endure way more. Come up with the most unique methods, prepare for a nightmare. Nobody leaves their psychological cabinet of a twisted "romantic" fantasy without being as damaged as they are. They are so masochistic that they join their prey. For instance, a 4w3 villain would bury themselves alive with their arch enemy.
100% eccentric, defying every villain stereotype there ever was. Will also strive to out-evil others, just experimenting a lot more to "understand themselves". Sits in a remote bunker, pressing buttons to trigger self-invented chemical bombs and plagues to bring the planet into despair. Might imprison their favourite sufferers and turn them into fetish objects to cry about all night. Televises themselves as everyone dies: "See! That's how it feels like to live among you basic peasants! See how defective you are, it's not me! Now you know the truth about living. This is hell!". Continues until they are the only person left so they can finally feel special without competition. Writes a tear-jerking diary about how much it hurts.
The invisible one. Kind of like the 4w5, just with fancier weapon technology and a philosophic-scientific framework that justifies what they do. Superiority complex... they just love to be better than you. Connoisseurs. Blow up the world to prove to themselves how capable they are. Has spent years of research about their targets, know their opponents better than they know themselves. Might as well be the secret leader of HYDRA. Kills people from afar. Being a villain is like a laboratory job to them: "Let's see what happens!". A very, very private villain, with refined taste and lots of stylish methods that they have worked on perfectionistically. Their plans are so complex and failure-proof that even the MI6 gets into trouble. Brainiacs who love to play chess - just with humans, not pawns.
A complete mastermind of social psychology, observing detachement is their strategy. Keeps their distance but still manages to find out everything about their target(s). Sneaky, expert of all things espionage and robbery. The most covert and grounded villain, intellectually advanced and difficult to be figured out. Uses riddles and blackmailing. Have a perfected and constantly evolving knowledge pool of the world which they can exploit through loopholes. Into financial types of villainousness. THE hacker of the enneagram, take care of your million-dollar company. Knows all of your codes, not sorry about it. The coldest of them all.
Creates a patriotic power monopoly that nobody can take away from them. Infiltrates the system from the inside out, all while benefiting from the pitfalls of society. Strong bonds with fellow patriots, organizes everything in groups that they are in total control of. Reigns by dividing, the #1 person to cause a civil war. While the world is in flames, they chill out on a safe island with their friends, reading a book. Gives mixed signals which confuses their adversaries. An expert at knowing fear - can mirror it to their victim and indulge in their angsty fantasy coming true. Some of these villains are never actually in charge, but control the actual leader in a covert manner. The most evil advisor there is, their poisoned minds always ready to infect others. Unleashes zombies if necessary.
Enthusiastically overthrows the government as if it's nothing. The pinnacle of an army leader, becomes their ultimate luminary - the "best" one of his or her kind. Tanks are their cute toys, war is their favorite pastime. Sitting in the Capitol eating grapes while the Hunger Games go down, this is basically what a 6w7 villain does with much delight. Behind high walls, their vigilant hedonism can blossom while others suffer. Great capacity for sadism. Completely paranoid - therefore, has countless back-up plans and strategies, just in case. Their anxiety causes them to erradicate everyone out of distrust once they sense that something could be wrong. And they will, because these villains are intelligent without showing it.
Being a badass is soooo much fun, right. This type is a polished gang leader par excellence. Crushes their opponents under their expensive car or shoe. The type of villain to wear designer clothing. May stage a box-to-death fight between their captives just because it's so exciting. Best described as a Roman emperor who sees the world as a Colosseum. "Panem et Circenses for the people!!", they shout as blood is splattering from every side. If you hurt co-villains they care about and depend on, prepare for the worst. Will attack society through their insecure points, granting them eternal satisfaction. Shoot to thrill. Will act more scattered than they really are - in fact, the 7w6 villain knows EXACTLY what they are doing. Will play truth or dare, Russian roulette or a lethal drinking game with you.
Oh my... so much mischief. Has the most elaborate, messy methods of vengeance that he or she can enjoy. Just like the 5w4 villain, they have a bunch of sparkly mass destruction weaponry. You know, they just need to make their program of revenge a worthwhile one. Pretty much unstoppable when their adrenaline is going through the roof. Junkies who expose themselves to danger, similar to the 4w3. Exponential growth, they constantly challenge themselves. Kings and Queens of Horror. Highly dangerous due to their propensity for arbitrariness and explosive whims. Completely lawless and unpredictable. Has more creative shenanigans up their sleeve than you ever will. Wedding crasher. Will rain on your parade just to get a kick, and that won't go down in a very sophisticated manner. Fashion forward. Their flirts are deadly.
Pretty much the most openly defying baddie in this collection, the only good thing being that they seem more powerful than they actually are to hide their one weak spot. A raging ruler who blows every threat out of proportion, their Kylo Ren-like outbursts frighten their minions more than actual opponents. If they have minions, that is - the 8w7 villain is usually a DIY type. Wants to seize and/or destroy everything, "I do what I want and you can't stop me"-style. Is in charge or else. Very intense. Can sometimes surprise an opponent by showing magnanimous mercy. On the other hand, disrespects other villains, becoming a lone wolf. Antisocial². Torture involves bodily fluids, and that's just the tip of the iceberg. Controls others by attacking their beloved ones and having lots of fun with them. Hunter and prey games galore, obsessed about "meeting their match".
The matriarch/patriarch. Will sell your soul without blinking. CEO of Intimidation Inc., roasts everyone who even remotely behaves in an intrusive way. Strips enemies off their privileges to have it all. A quintessential extremist who marches through every obstacle - basically every science fiction badass ever. May encourage their victims to try harder. Might seem chill on the first glance but erupts in 0.01 seconds when provoked, literally out of nowhere. Hence, this villain is a legit time bomb. Always in defense mode, submitting as many people to their cult as possible. Signature weapon: a whip. Always part of the villain elite.
The scary guru. Has indoctrinated everyone with their mentality of "peaceful violence". Master of psychoterror, meditates before battle. A zealot like the 1w9 villain, just more ruthless - after adapting to their target on a spiritual level. Uses a conglomerate of psychedelic drugs and other questionable substances to get what they want. Smashes everything and everyone who causes them distress to create a "harmonious" world. Has chained their minions to their ankles so they won't leave him or her, but doesn't feed them enough so they can rebel and free themselves. Sacrifices humans to create an elexir to stay forever young and immortal.
The teacher type of villain. Gathers a large following with books and speeches that feign a harmless, accomodating stance. Once this gathering sticks to the villain like glue, they start a "counter-movement" that establishes a new, immaculate system. Everything that goes against this villain's set of values is punished through imprisonment and a "cleansing" of some kind. Each or their pupils is obedient, pure and meek. By any means, it is forbidden to upset the enlightened 9w1 villain through misconduct. Dangerous as they don't seem capable of doing evil at all. Lets others do the dirty work while they sit in their ashram. Makes sure you learn your lesson properly.