Shao Kahn stands as one of the most iconic, feared, and loathed bosses in video game history. Debuting in Mortal Kombat II as the game’s final boss, the imposing Emperor has remained a series mainstay for over 20 years. His popularity as an antagonist has been proven by the revolving door of villains to take his place following his downfall in Mortal Kombat 3. Despite the number of new, impressive adversaries, Kahn is still viewed by many fans, myself included, to be Mortal Kombat’s one true ultimate evil.

You don’t earn that title without making a few corpses along the way. The skull-wearing tyrant has committed an unfathomable amount of terrible deeds. Like some of the baddest of bad guys, he possess no redeeming qualities, making him the ideal adversary to want to punch continually in the face. Kahn is far from a push-over though. His capacity for evil is only matched by his extraordinary combat prowess. Putting an end to his reign is much easier said than done. In that way, he’s the perfect video game boss: easy to hate and incredibly challenging to defeat.

A guy with his track-record made it quite easy to compile a list of 20 mind-blowing deeds. Fishing the most worthy ones out of the ocean of blood he’s left was where the challenge lied. But whether it's forced marriages, killing fan favorite characters, or boasting seemingly insurmountable difficulty, here are 20 of the most eye-brow raising acts Outworld’s infamous ruler has ever committed.

20 Poisoning Onaga, The Dragon King

Believe it or not, Shao Kahn didn’t always have an iron grip on Outworld. He himself once answered to an overlord in the form of Onaga, the Dragon King, who reigned over Outworld long before it became fashionable. During this time, Shao Kahn served as an adviser to Onaga. Secretly, however, the budding ruler plotted his ascension to the throne because that’s what evil runner-ups do when their evil masters aren’t paying attention.

Shao Kahn knew he wouldn’t fare well against Onaga in a straight-up battle, so he opted to poison him instead. An underhanded tactic for sure, but just look at Onaga in the image above. Would you want to spar against that? The plan worked, and with the Dragon King out of the picture (for a good while, at least), Shao Kahn took the throne and began his conquest to merge all of the realms under his rule. Nothing like a good old fashioned back-stabbing to kick off a reign of terror.

19 Conquering Edenia And Merging It with Outworld

Shao Kahn gets his jollies from conquering other realms and merging them with Outworld. He’s the walking definition of a hostile takeover. Kahn has absorbed numerous worlds, but his most famous victory came when he took over the paradise-like realm of Edenia. Outworld won ten consecutive victories in Mortal Kombat which granted Shao Kahn the deed to the Kitana family doorstep. Now when takeovers of this sort occur, most people automatically assume it’ll be for the worse. But did Shao Kahn really ruin things?

Sure, he would enslave the Edenians, a culturally rich and generally peace-loving race. Then he ousted King Jerrod by killing him before the eyes of his wife, Queen Sindel. Kahn would also cause the overall deterioration of one of the most beautiful and prosperous realms in the history of, like, ever. Okay, so maybe things took a slight turn for the worse. Edenia would become remain pressed under Kahn's thumb for 10,000 years until Liu Kang came along and helped free the realm due to his triumph in Mortal Kombat.

18 Forcefully Wedding Sindel (Then Drive Her To Suicide)

Shao Kahn wed Queen Sindel in order to help legitimize his hold on Edenia. By that, I mean Sindel was forced into marriage with a ceremony that likely saw the “I do’s” replaced with the Emperor shouting at her to “FEEL THE POWER OF SHAO KAHN!”

Sindel was...less than pleased with this arrangement, to say the least. Between the loss of her realm, witnessing her husband’s demise, and the adoption her infant daughter by a tyrant, life became too much to bear. Soon after the marriage, Sindel took her own life. But like any good husband-by-force, Shao Kahn wouldn’t allow Sindel to escape him, even in death. He used his black magic to trap Sindel’s soul, preventing it from passing into the afterlife. Husband of the Year, ladies and gentlemen. Turns out he would have some grand schemes in store for the soul of his “beloved”. We’ll touch on that a bit later.

17 Kidnapping Kitana And Raising Her As His Daughter

Child abduction is generally frowned upon, but that didn’t stop Shao Kahn from stealing the infant princess of Edenia. He did so to further strengthen his claim of Edenia, but I like to think that he just has a soft spot for cute babies. Regardless, positioning yourself as the father of a child whose real pops you slaughtered is pretty bad form.

As Kitana very slowly grew older, she was increasingly brainwashed to view and adore Shao Kahn as her real father. As you would expect, Kahn withheld the information regarding the fate of her actual family. He would spend countless years manipulating Kitana, using her as his own personal assassin and protector. One can only imagine the vile acts he made the princess perform during numerous centuries. Despite her overwhelming loyalty, Shao Kahn still treated Kitana like the world's most attractive garbage pile whenever she didn't perform at a satisfactory level.

16 Green-lighting The Creation Of Mileena

So that horrifying visage of death you see above? You can thank Shao Kahn for that nightmare. Dissatisfied with his own adopted daughter, the Emperor opted to simply make a better one. If you can’t beat ‘em, clone ‘em! Shao Kahn gave his right-hand sorcerer Shang Tsung the go-ahead to create Mileena, a near-perfect clone of Kitana, but without that pesky conscious of hers.

Some of the princess’ good looks were left on the table as well. Mileena’s mix of Edenian genes with that of the grotesque Tarkatan (the race Baraka belongs to) resulted in her signature Street Shark-esque smile and mental instability. That sounds like a disaster, but Mileena was exactly what Khan desired: a loyal and ruthless killing machine that could pass as the princess– as long as someone wasn’t curious enough to ask what the deal with her veil is. Kahn spitting in the face of nature by commissioning the creation of his own monster mostly paid off. Mileena would prove to be a disturbing and formidable thorn in the heroes’ sides for many years.

15 Killing Johnny Cage 

Mortal Kombat: Annihilation is a terrible, terrible film. One of the myriad reasons for its sucktitude stems from the mind-boggling decision to murder Johnny Cage, i.e. the most entertaining personality from the previous film.

If you’ve never watched the movie (lucky), the opening minutes see Liu Kang and pals confront the newly arrived Shao Kahn. Cage, the Rhodes Scholar that he is, decides that charging at this new foe alone is the key to victory. That earns him a prompt (and heartbreaking) neck-snap from the disappointingly under-sized, live-action Emperor.

My world fell apart watching this scene as an MK-obsessed child. This would be like Darth Vader offing Han Solo at the start of The Empire Strikes Back. Just like that, the super cool guy is gone, and we’re left with a party of stoic sad sacks plus a weak comic-relief replacement in Jax. All thanks to that stupid jerk, Shao Kahn.

14 Relentlessly Taunting Players During Battle

“YOU WILL NEVER WIN!” “BOW TO ME!” “And who could forget the classic “It’s official…YOU SUCK!” Sometimes plain old mocking laughter gets the job done too. Before cyber-trolling became commonplace, Shao Kahn established himself as the king (or, I guess, Emperor) of spewing verbal abuse. He would easily rule the roost of many online multiplayer lobbies.

Some say the only thing worse than getting beat up is having to endure the insults of the person delivering the beating. Shao Kahn proves that statement accurate by making his excruciating bouts (oh, we’ll get to that) more unbearable with well-placed, demoralizing verbal jabs. He’s basically the jacked-up version of that arrogant friend you play fighting games with. You know, the ones who can’t stop filling your ears with tales of their supposed greatness. But unlike that friend, who you can silence with a swift punch to the shoulder, Shao Kahn can’t be quelled as easily. And yes, Kahn, I AM still trying to win.

13 Driving Players To Insanity With His Super Cheapness

Defeating Shao Kahn is hard. Like, really hard. Like, trying to dodge rain in a thunderstorm hard. In Mortal Kombat II and 3, the insufferable jerk spams those punishing Shadow Charges like no tomorrow. He also seems to possess an annoying precognition, knowing exactly when players will jump to immediately counter with the aerial variation of said Shadow Charge.

You’d think pitting two opponents against this beast would ease things. The two-player Mortal Kombat: Shaolin Monks debunked that theory by featuring what's arguably the most challenging Kahn fight ever. Other may point to the aneurysm-inducing ordeal that is facing Kahn in 2011’s Mortal Kombat as giving Shaolin Monks a run for its money.

Video game final bosses should absolutely bring the fight. Shao Kahn regularly crosses the line from “tough but fair” over to “GOD HELP ME, WHAT HAVE I DONE TO DESERVE THIS?” Any torture artists out there should strongly consider adding never-ending Shao Kahn boss battles to their arsenal.

12 Trying To Marry Sonya Blade

I had to do a double-take when I discovered this. So Mortal Kombat had a series of comics in the 90s published by Malibu Comics. In one story, Shao Kahn devises a new method to invade Earthrealm. In other words, the sky is blue. Although this time, his plan was to abduct staple Earthrealm defender Sonya Blade and marry her. The union would erase the borders separating Outworld from Earthrealm, giving Kahn an express ticket into our world.

This idea worked with Sindel to a degree, so I guess I can’t fault Kahn’s logic there. And unlike the late Edenian queen, who was basically told to just deal with her situation, Kahn opted to hypnotize Sonya into willingly giving herself up to him. Kahn clearly learned from his mistakes after what happened to his last wife. Of course, the entire ceremony devolves into a chaotic free-for-all before the marriage could be made official. But it's an odd little nugget of MK lore.

11 Providing Commentary For Every Battle

While not a WTF moment in the traditional context, discovering that Shao Kahn was the person announcing all of the fights blew my mind as a kid. Reaching him at the end of MK II and hearing him declare “You will die!” rather than the traditional fight intro was a combination of cool, creepy, and intimidating. I remember wondering if he would declare himself the winner during our confrontation. Turns out he preferred a hearty laugh instead. Figures.

Shao Kahn’s commentary is one of the neatest little touches of the older games that actually helped make him more threatening, at least to me. I had so many questions. How is he witnessing all of my matches if he’s not physically present? How could he know I was “superb?” Is he omnipresent? What if he’s watching me know, making snide comments about my actual shortcomings? Fighting him felt like facing the narrator of a story who decided to enter the tale himself at the last minute. It’s definitely one of the most surprising aspects of Shao Kahn’s character.

10 Merging With Darkseid

Mortal Kombat vs. DC Universe was a strange cross-over that saw Scorpion trade blows with Wonder Woman because why not? Perhaps the most bizarre thing to occur was when Shao Kahn involuntarily fused with DC’s top baddie, Darkseid. This union gave birth to, wait for it, Dark Khan because Shao Seid sounds very silly.

Throughout the game’s story, Dark Khan dwelled within the joined realms of Outworld and Apokolips, and used his power to influence the combatants with “Kombat Rage.” Those infected by this magic were driven mad by an insatiable blood lust and wanted nothing more than to cave in the face of anyone put in front of them. That’s a powerful ability, evident by how both sides mercilessly beat the tar out of each other. Though I doubt The Joker ever needed much reason to maim someone regardless.

Commanding that kind of power, Dark Khan was seemingly unstoppable. It took Raiden and Superman’s combined power to finally bring him down.

9 Possessing An Unhealthy Fetish For Slavery

Shao Kahn has no qualms about snuffing out the life of his enemies. But the Emperor appears to derive greater pleasure in keeping them alive and drawing out their misery. Even back in his first appearance in Mortal Kombat II, Kano and Sonya Blade are shown shackled next to his throne. Simply killing one of his primary foes would probably be a better idea (and I guess Kano too just for...having a weird laser eye), but why do that when you can have an attractive trophy? In 2011's Mortal Kombat, various fighters are once again shown to be imprisoned at his arena, including Tanya and Skarlet. Kahn really has a thing for chaining up women, going as far as to rip Jabba the Hutt’s gimmick by having his own version of a slave Leia (pictured above). If he doesn’t throw opponents in chains, those willing to serve are often made into subordinates. Honestly, that’s probably the better, less degrading, offer.

8 Escaping DC's Phantom Zone

After Dark Khan was toppled in MK vs DC, he reverted back into the two beings that forged him. Darkseid found himself cast into the Netherrealm. Shao Khan was doomed to the Phantom Zone.

For non-DC comics fans, the Phantom Zone is a prison dimension that houses big time Kryptonian criminals. Inmates aren’t wholly alive but aren’t quite dead either, so it functions a lot like a type of limbo than a traditional confinement. One of the dimension’s nifty effects is that it neutralizes the inhabitants’ powers, keeping them in check.

Thus, the Zone should have de-powered Khan. Unfortunately, his personal game ending revealed that the Phantom Zone had the inverse effect of supercharging the Emperor’s strength. This allowed him to break free of this prison. As if that backfire wasn’t colossal enough, his escape caused all of the Zone’s prisoners to escape, who showed their gratitude by swearing their allegiances to Kahn. Backed by an army of P.O.’d Kryptonians, Shao Khan launched a campaign to conquer the universe.

7 Breaking Tournament Rules By Invading Earthrealm

Liu Kang taught Shao Kahn his first lesson in humility by defeating him in Mortal Kombat II. Per tournament rules, Kang’s victory should have protected Earthrealm from an Outworld invasion. Ever the sore loser, Kahn would invade our realm anyway in Mortal Kombat 3. He’s a jerk like that, you see. If blatant rule-breaking wasn’t bad enough, he achieved this by resurrecting his dead wife to act as an undead loophole around the tournament rules. You know, Sindel, who took her own life because she couldn’t stand being enslaved by an evil tyrant. As if being miserable in life and being denied eternal rest wasn't enough, she got to become an evil pawn for the emperor’s gain. I'd argue that’s a fate worse than death. Clearly there are no depths this guy won’t sink to in order to get what he wants. Unfortunately for us humans, Kahn’s first order of business in Earthrealm was to…

6 Stealing The Souls Of Earth's Entire Population

We can also add genocide to Shao Kahn’s long rap sheet of atrocities. Upon his arrival, Kahn wasted no time absorbing the souls of nearly every person once he arrived. The “lucky” few who managed to escape this fate were hunted down by his extermination squads.

Obliterating humanity is undoubtedly appalling, but it's also a remarkable achievement in villainy. Think of all the bad guys in history who have aspired to wipe out or enslave humanity. How many of them pulled it off? Shao Kahn sits among the likes of Final Fantasy’s Kefka and Dragon Ball Z’s Majin Buu in elite club of evildoers who have actually managed to wipe out Earth–and in grand fashion at that. Raiden managed to protect the souls of Earthrealm’s warriors who went on to defeat Kahn and wholly reverse his damage. But never forget that for a brief moment Shao Kahn had undisputedly won.

5 Defeating Raiden

Raiden is the God of thunder and lightning (watch out, Thor) and protector of Earthrealm. He’s the ultimate voice of wisdom and sometimes acts as the get-out-of-jail free card when the forces of light find themselves in a pickle. Raiden has always been portrayed as an all-powerful being, to the point that it became tough to see him lose to anyone. But that’s exactly what Shao Kahn did. He bested the good guys’ biggest gun not named Liu Kang.

Not just bested, but pummeled Raiden to within an inch of his divine life. In Mortal Kombat: Armageddon, he’d so thoroughly trounced the God that he needed to resort to time-traveling in order to stop Kahn. Somehow topping Raiden wouldn’t be confined to just video games. Kahn outright killed him in the Annihilation movie, as well as beat him in the final episode of Mortal Kombat: Konquest TV series. Kahn doesn’t just have Raiden’s number, but his phone and probably his entire service plan too.

4 Transforming Into A Gross Hydra Thing

Hey, more terrible-ness from MK: Annihilation! Remember Animalities? If not, they were unique finishers introduced in Mortal Kombat 3 that saw the Kombatants go full-on Animorphs (remember that?) by transforming into various beasts and subsequently murdering people. Animalities became popular enough to earn them a key role in the second film (despite ultimately amounting to nothing).

Shao Kahn went beast-mode for the first time in series history during his climatic battle with Liu Kang. After the MK champ morphs into his signature dragon form, Kahn counters by twisting into what can only be described as a multi-headed meat-sack that could fuel a six-year old’s nightmares until they turned seven. The ensuing clash of monsters was as hideous as the beasts themselves thanks to the laughably poor animation and CG effects.

3 Winning Armageddon

Mortal Kombat: Armageddon was billed as the final chapter in the epic MK saga–the first one, at least. Every fighter to ever throw an uppercut engaged in a massive battle to determine the fate of the realms once and for all. The prize was Blaze, a God-like entity who awaited atop a pyramid for whoever survived the conflict. Defeating Blaze would grant the victor unspeakable power.

Guess who stood tall in the end. Yep, Shao Kahn, who ascended the pyramid after having outlasted three Gods, a Dragon King, an undead former champion, roughly 27 ninjas, and Mokap. Raiden was his final opponent, and we all know how favorable that turned out for the Thunder God. This was quite the comeback for Kahn when you consider that prior to Armageddon, the last time he was truly on top was Mortal Kombat 3. Unfortunately, ultimate power wasn’t quite all it was cracked up to be.

2 Driving Himself Insane After Conquering Everything

If you haven’t realized it by now, Shao Kahn has an obsessive compulsive need to conquer things. Realms, magic, personal relationships, the arts and sciences (probably). If you have it, odds are Kahn wants it. But at the alarming rate he consumed worlds, sooner or later he was going to run out of things to dominate. What would he do then?

Mortal Kombat: Armageddon poses this intriguing question in Shao Kahn’s arcade ending. After attaining Blaze’s power and more or less becoming a God, Kahn runs amok absorbing realms left and right. Since no one can oppose him, Kahn achieves his life-long goal rather easily. But it turns out that it was always about the journey more so than the destination. With no adversaries left to challenge him, Shao Kahn loses his mind, likely out of crippling boredom. What do you get the conqueror who has conquered everything? Some fresh challengers, apparently.

1 Constantly Evading Death In A Series Filled With It

Mortal Kombat is a lot like Dragon Ball Z in that characters perish and come back to life so often that it’s lost a lot of meaning. You know who hasn’t ever really died? The big bad dude wearing the skull helmet. Looking at all of his appearances, and taking canon into account, Kahn has only been defeated or repelled but never truly vanquished. Mortal Kombat: Deadly Alliance’s opening cinematic features a scene of Shang Tsung and Quan Chi supposedly killing Kahn. However, that was later revealed to be merely a clone.

The closest Shao Kahn has come to pushing up daises occurred when Raiden defeated him at the conclusion of the 2011 reboot. However, even that was a vague demise as the scene could easily be interpreted as the Elder Gods sentencing Kahn to eternal imprisonment, not a flat-out execution. How has no one ever killed this guy, even once? Hanging on this long in the overwhelmingly life-threatening Mortal Kombat universe is an accomplishment best summed up by saying W.T.F.