The 22 most frustrating video game bosses of all time (and how to finally beat them)

in #gaming7 years ago (edited)

Great video games usually have great bosses, too--ones that offer a fun, exciting, and balanced battle. Some bosses are naturally harder than others, but a few definitely deserve the notorious reputation they've earned over the years. If you've spent any time at all playing video games, you probably know exactly what I'm talking about. These bosses might be super-difficult or take a ridiculously long time to beat. Or maybe it's an extremely boring fight, or the encounter is poorly designed, buggy or just doesn't work right. These are the bosses you fight until you can't feel your thumbs, the ones that make you want to tear your hair out, the ones that make you scream, "JUST DIE ALREADY!" as you launch your controller across the room. You've been there. You know the pain, the misery, and the frustration. 

In no particular order, here's my list of 22 of the most frustrating video game bosses of all time. Where appropriate, I've also included links to strategy guides to help you finally beat them. If there's one you think I missed, be sure to share your thoughts in the comments, or hit me up on Twitter!

Yiazmat - Final Fantasy XII

Over the years, the Final Fantasy franchise has given rise to some ridiculously hard bosses. In 2006's Final Fantasy XII, that boss is Yiazmat. This legendary dragon has over 50 MILLION health points. Yiazmat's insane amount of HP should be your first clue that you're gonna have a bad time. Just to illustrate how ridiculous that number is, a player going up against Yiazmat for the first time might have a party that average just 6k to 10k HP.  On top of that, Yiazmat has some special abilities that make him even more frustrating. Once you get him down to 25 million HP, all of your attacks are capped at just under 7k damage. If we do the math, that means you'll have to hit Yiazmat another 3,571 times (at 7k damage each hit) just to kill him. 

In a traditional turn-based RPG, that would be a mind-numbing slog. Thankfully, FFXII has a more "real-time" combat setup, and a unique (for Final Fantasy) Limit Break system that lets you string together attacks into devastating combos. That makes the fight with Yiazmat a little bit more reasonable--but these "Mist Chain" combos rely entirely on timed button-presses. If you're good at that sort of thing, Yiazmat might take you an hour to beat, but most players will need a good 3 hours or more to finally kill him off. If you're feeling nostalgic or if you're just a glutton for punishment, there's no need to dust off the PS2 to try Yiazmat again. In late 2017, Square Enix released an HD remastered version for PlayStation 4: Final Fantasy XII: The Zodiac Age.  Be warned: Yiazmat is just as much of a bastard this time around, so make sure you check out a strategy guide first.

Whitney and her Miltank - Pokémon Gold & Silver

Okay, so a Pokémon gym leader probably wasn't what you were expecting when you opened this post, but Whitney from 1999's Pokémon Gold & Silver definitely belongs here. The Goldenrod Gym Leader is a Normal-type specialist, and you might be expecting an easy fight when you face her. However, one of her Pokémon can turn this battle for the Plain Badge into one of the most "udderly" frustrating fights of the entire franchise. After Whitney's Clefairy goes down, she brings out her secret weapon: a deceptively-cute Miltank who is about to ruin your entire day. 

This particular Miltank of Doom™ has moves which will turn this seemingly easy match into a protracted battle. Get in a lucky super-effective hit? Miltank will heal itself with Milk Drink. Manage to get ahead of Miltank in HP? It uses Stomp to make your Pokémon flinch and miss a turn. Have male Pokémon on your team? Miltank will use Attract to make them refuse to attack. Most importantly, Whitney's Miltank knows Rollout: a Rock-type move that will hit you with ever-increasing damage for FIVE TURNS. If you don't get handed a quick defeat by this cute little cow, it's likely that all your Pokémon will eventually run out of PP. Next time, bring a MysteryBerry or two to refill PP in a pinch, and check out this strategy guide for some more tips.

The End - Metal Gear Solid 3

He's over 100 years old, has false teeth, falls asleep a lot, does this really creepy thing with his eyes, and owns a weird animal that rides everywhere on his shoulder. He also has the skills to kill you in any number of ways--if he wanted to. No, I'm not talking about not your crazy Great-Uncle Murray. I'm referring to Cobra Unit's legendary sniper "The End" from 2004's Metal Gear Solid 3. The sniper duel with The End is a frustrating test of your skill, stealth, patience, and endurance. Until you have a few MGS3 playthroughs under your belt, slow and steady is the only way to win this race. The End is a camouflage expert, and can spend days or even weeks in the same position while lying in wait. His pet parrot keeps an eye out for enemies while he sleeps. What's more, an unknown parasite infection gave him unnatural longevity and the ability to get nourishment from the sun's rays. That's right, this tough old sonofabitch uses photosynthesis to survive and has a parrot as his spotter. What. The. Hell. 

As you've probably gathered by now, letting your guard down for a moment or trying to rush this fight is a bad idea. Underestimate The End, and you'll end up with a tranquilizer dart in your butt and a one-way trip back to the Graniny Gorki jail to start over. You're going to need some finesse if you want to track down The End while staying out of his extremely accurate sights. There are some cheats available (like sniping him early, using the Konami Code on the map, or making him die of old age), but you should at least try to beat him the old-fashioned way the first time. It's pretty thrilling when you finally manage to pull it off. Defeat him non-lethally and you can even earn his special camo and modified Mosin-Nagant sniper rifle. If you're a MGS3 virgin or trying a harder difficulty, plan on spending a couple of intense hours holding your breath. I don't mean that figuratively, either. No, you'll actually be afraid to breathe--lest you miss the tiny auditory clues that indicate you're getting close to "the end" of this boss fight. Here's a strategy guide if you need some help.

Mike Tyson - Mike Tyson's Punch-Out!!

Next on my list, we're kicking it old-school with 1987's Mike Tyson's Punch-Out!! for the Nintendo Entertainment System. It's been more than 30 years since Mike Tyson himself laid his claim to the "most frustrating" title, and he's still a strong contender today. The biggest problem with the final bout with Iron Mike is how unpredictable he is. Unlike many of the other fights in Punch-Out!!, Tyson's moves are extremely hard to anticipate and the "tells" he gives you are often purposefully misleading. Every hit he lands on you during the first minute and thirty seconds results in an instant knockdown. On top of that, he's huge compared to your character. His size, speed, and powerful attacks will leave you with very little chance of even landing a punch on the heavyweight champion. 

Unless you get a lucky TKO on him in the second round, the only way to beat Mike is usually to spend hours fighting him over and over until you've memorized all of his moves (and the order they usually come in). His attacks might seem essentially random, but there apparently is a pattern if you know what to look (and listen) for. At the 2016 Awesome Games Done Quick speedrun event, two amazing gamers actually managed to beat Punch-Out!! while blindfolded. You can watch the full video here, or skip to the Tyson battle. Still stuck on Iron Mike? Here's a strategy guide that might help you finally earn that champion belt.

Boss Rush/Yami - Ōkami

I think many people would agree that Ōkami is one of the best action-adventure games of all time. After an underwhelming (but critically praised) initial release for the PlayStation 2 in 2006, Ōkami has gone on to become massively successful and has been ported to several other platforms. Most recently, an HD remaster of Ōkami was released for PC, Xbox One, and PS4 in December 2017. The graphics may have been given an upgrade, but one thing definitely hasn't changed: how hard the final boss is. In Ōkami, you face a "boss rush" at the end of the game. This means you have to fight all the bosses you beat earlier in the game, beating them again one after another, before you finally face the last boss of the game. 

If you can successfully make it through this boss rematch gauntlet, you'll go up against Yami. A couple of things to know about Yami: he's the machine-like Lord of the demons in Ōkami, and he is extremely powerful. How powerful? Oh, I don't know--he just killed nearly all of the Gods long ago, thus setting up the story of the game. Does that answer your question? Sure, Amaterasu (your character) is a goddess, but that means precisely zilch if you don't have the skills to win--and you won't, at least not to start with. Amaterasu loses all of her powers just before the fight begins, and you must earn them back one-by-one during this long boss battle with Yami. The demon also shifts through five different forms and phases, which all offer up their own unique challenges. When all is said and done, the boss rush and fight with Yami will probably take you a couple of hours or more to finish. Need help? This strategy guide should get you started. 

The Rebel Flagship - FTL: Faster Than Light

In the 2012 roguelike spaceship simulator FTL: Faster Than Light, you go up against a number of challenging encounters during your travels through eight different sectors of space. Unquestionably, the hardest of these enemies is the extremely powerful Rebel Flagship. The Rebel Flagship acts almost like a traditional video game "boss," as it changes abilities and strategies in each phase of the battle. What's more, the AI controlling the Rebel Flagship is pretty damn smart--meaning you'll really have to think fast and stay on your toes during this fight, which occurs entirely in (pausable) real-time. The Flagship also has unlimited ammunition, which stacks the odds even higher against you. Also, death is permanent in Faster Than Light. If your ship blows up or all the crewmembers die, you have to start the game over from the beginning. Sounds totally unfair and rage-inducing, right? That all depends on your mindset.

Here's what I'm trying to get at: YOU WILL NOT BEAT THE REBEL FLAGSHIP ON YOUR FIRST TRY. You might not even be able to beat it on your tenth try--even in normal difficulty. Just accept the inevitability of your repeated failures now, and you'll have a much better time enjoying the challenge of taking the Flagship down. FTL is all about making good choices about upgrading your ship from the start of the game, and learning how to effectively fight and switch tactics on the fly. If you are still stumped by this enemy spaceship, check out this strategy guide for some tips and tricks.

Nyx Avatar - Shin Megami Tensei: Persona 3

Some games like to pit you against the same boss multiple times in a game, making them harder each time you meet for a rematch. The Zelda game series is a prime example of this. Seriously, how many times have we defeated Ganon/Ganondorf so far? I know, I know...there's all sorts of different timelines and dimensions involved there, but you still know what I mean. The 2006 RPG Shin Megami Tensei: Persona 3 takes a page from Zelda's book by having you go up against the demon Nyx twice in the same game. The second time around is the final fight of the game, and the female Nyx takes an avatar in the form of your male classmate Ryoji--who has some dark secrets of his own. 

Nyx is the manifestation of Death, and Ryoji has a definite melancholic streak hiding under his flirtatious (and sometimes perverted) surface. The fight with Nyx Avatar is a life-and-death battle with an emo demon who wants to end all of existence--but who is also totally in love with you. Pretty heavy stuff, man. Beyond the emotional conflict Persona 3 is so good at, the fight itself is no walk in the park--it can easily take an hour or more to finish. Nyx Avatar goes through fourteen different phases during the battle, and her final form can be extremely difficult. She can reflect your attacks and deal major damage, and can even use a Charm spell to make an infatuated member of your party give her a full heal. Give this strategy guide a look if you need some help beating Nyx.

Sephiroth - Kingdom Hearts I and II

The mysterious swordsman Sephiroth made his first boss appearance back in Final Fantasy VII. He was no pushover in FFVII, but Sephiroth got even harder when he returned for both Kingdom Hearts and Kingdom Hearts II. Thankfully, the boss fights with Sephiroth in the KH games are optional. Even maxed-out players who have the powerful "Ultima Weapon" will find Sephiroth is still extremely hard to beat in Kingdom Hearts. You'll need a well-practiced strategy and lots of healing elixirs in your bag. Seriously, bring as many elixirs as you can stuff in there. What's worse, every time you die facing Sephiroth in KH1, you have to watch a long cutscene before you can try again. If you have a PS3, just get the HD version of the game instead: Kingdom Hearts HD 1.5 Remix. The fight mechanics and difficulty are the same, but at least you can skip that torturous cutscene. 

In Kingdom Hearts II, Sephiroth is back with his big-ass sword Masamune and more brutal moves to punish you for attempting to beat him. He keeps the most devastating skills from Kingdom Hearts (like his "Heartless Angel" one-shot attack) and also adds new ones to his repertoire: like some nasty little black orbs of pain that home in on you like evil torpedoes of doom. DOOM! At least if you beat him in KH2, there is a shiny new keyblade waiting for you at the end of the ordeal. The original Kingdom Hearts doesn't give you a damn thing for defeating Sephiroth--except maybe some early-onset arthritis from all the rage-filled button mashing you'll do.  Here's a strategy guide for beating Sephiroth in Kingdom Hearts, and one for beating him in Kingdom Hearts II

Abyssion - Tales of Symphonia

Much like Sephiroth in the Kingdom Hearts series, Abyssion from the 2003 roleplaying game Tales of Symphonia is entirely optional. To fight him, you'll first have to suffer through a mission that will leave you seriously questioning the intelligence of your party. After the group first meets Abyssion, he sends them on a seemingly altruistic quest. Paraphrased: "Hey guys, go fetch these *cough* cursed *cough* weapons for me, I'm totally going to lock them away forever to keep the world safe." He conveniently forgets to mention that these weapons (called the "Devil's Arms") can turn anyone exposed to them completely insane, but that's just a minor detail: just "don't listen to the voices," and it'll all be fine. You dutifully trot off to recover the Devil's Arms from the places where they were already hidden safely from the world. Throughout it all, only one character even expresses any concern about collecting cursed weapons to deliver to a complete stranger. It's a lot like watching a horror movie where a bunch of teens make some really stupid choices that get them killed. 

After you go collect all nine Devil's Arms for Abyssion--SURPRISE!!--he turns on you and takes the weapons for himself. Who could have predicted that? *eyeroll* You finally begin the boss fight, where he uses the Devil's Arms to turn your own skills against you. Just collecting the weapons takes quite a bit of time, but the boss fight with Abyssion is a true slog--one that will likely take an hour or more to finish. If you're really determined to beat Abyssion, then this guide should help you out. My advice? Do yourself a favor and just go watch Candyman or Evil Dead instead.

King K. Rool - Donkey Kong 64

Just like Ganon in Zelda and Bowser in Mario, King K. Rool has been the long-standing big bad of the Donkey Kong franchise. His first appearance was in 1994's Donkey Kong Country. In that boss fight, K. Rool pulls some truly nasty moves and even tries to fake his own death after Donkey and Diddy beat him. I can't be the only person who gleefully thought they had beaten him when I saw his fake "Kredits" start to roll, only to die instantly when he jumped up and started attacking again. This wouldn't be the last time the crocodilian trolled gamers in a boss fight. In 1999's Donkey Kong 64, King K. Rool fakes you out with a cardboard decoy of himself in the second-to-last boss fight, then appears for the final battle as his boxing alter-ego, Krusha.  

Did you just spend hours playing DK64 and getting comfortable with the game's mechanics and strategies? Too bad! Krusha K. is here to take everything you learned and throw it right out the window. Instead of a traditional boss fight, you face K. Rool in a strange boxing match punctuated by overly long cutscenes. To beat him, Donkey and the other Kongs have to do things like shoot themselves from cannons, drop the stage lighting on his head, and make him slip on banana peels--yes, really. Each "round" lasts three minutes, and you have to K.O. him in that time or he will be fully healed (while your health stays the same). If he beats any of the Kongs, or if you don't knock him out with each one of the team members in 12 minutes or less, the entire fight resets and you have to start over. Now that's just...Krool. Here's a guide on how to beat him if he's still got you stumped.

Mael Radec - Killzone 2

Okay, so the boss fight with Killzone 2's Helghast commander Mael Radec may not take as long as some of these others, but it's still extremely difficult--and will feel like an eternity while you're doing it. In a first-person shooter, any fight that lasts more than 10 minutes straight can be intense, but the 30+ minute battle with Mael Radec is enough to inspire a heart attack. The fight is essentially a "bullet hell," where you fight off waves of Helghast soldiers that appear rapidly, show no mercy, and get successively harder with each new wave. If you make it to the guys with rocket launchers, then congratulations!--you're about to die. 

If the elite Helghast troops don't blow you sky-high with their rocket launchers, then Mael Radec himself will come finish the deed. He's a combat expert, and Radec will gladly and easily kill you from a distance or up-close and personal. As if his specialized fighting skills weren't enough, Radec also gets a couple of items that can really turn the tide against you: a cloaking device and a teleporter. Unless you've got a your back to a wall, prepare for your demise when Radec inevitably appears six inches behind you for a pop-up stabbing. It will take a lot of time and practice with this boss fight to get your tactics and timing all just right. Need help? Check out this Mael Radec guide.

Ornstein and Smough - Dark Souls

I'm guessing that most gamers reading my list immediately looked for a Dark Souls entry. To be honest, the DS franchise is so filled with nightmarishly difficult boss fights, I could probably have populated this entire list with just various Dark Souls bosses from over the years. However, I had to pick just one battle...and I ended up deciding on the boss fight with the odd couple of Ornstein and Smough from the 2011 original, Dark Souls. Ornstein is an agile and lanky guy who loves to run you down with his spear if you're too close to him, and strike you down with bolts of lightning if you're further away. His partner in crime Smough looks like an armored Pillsbury Doughboy with a disturbing pair of man-boobs, but don't let appearances deceive you. This waddling warrior is faster than he looks, and he will promptly smash your head to a pulp with his big-ass hammer if you don't keep one step ahead of him. 

Don't bother fighting them simultaneously, it'd just be wasted effort: once you kill one of them, the other boss gets a full heal and also absorbs some of his dead buddy's powers. Who you take down first really depends on your character spec and what reward you want. Make sure to look up the loot for each scenario before you start this fight. The last thing you'll want to do after successfully beating Ornstein and Smough once is having to do it again because you screwed up the order.  Bringing Solaire along can help make the fight easier (Praise the Sun!), but all the jolly cooperation in the world won't save you from certain death if you don't have a good plan when you step through the fog. Here are some tips and ideas to formulate your strategy.

The Bloat - The Binding of Isaac: Rebirth

The Binding of Isaac: Rebirth is not an easy game, and many of the bosses can turn into a maddening roadblock if you aren't careful and learn from your mistakes. That said, "The Bloat" is easily the worst of the worst, and he's not even one of the game's final bosses. Bloat is so despised by most TBoI players, there is even an entire Subreddit made for the sole purpose of hating him. The Binding of Isaac is a roguelike dungeon game that somewhat randomizes levels as you play. Unlike a "normal" boss, Bloat has the chance to appear in several different spots throughout the game, and he can even pop up more than once if you're really unlucky.

Bloat's most devastating attack is what I call his 'eye beams of blood' move--which comes without warning and can easily one-shot you if you get hit by its extremely deceptive damage beam. His eyeballs also float around the room and will damage you if you wander into their path. There's even a "Champion" (read: ultra-difficult) Green version of Bloat, which adds new moves to his already punishing attacks. Just like in Faster Than Light, death is permanent in TBoI--so you'll have to start the game over from the beginning if The Bloat kills you. If you're still struggling to beat this blob of terror, here's a guide that may help.

Spider Guardian – Metroid Prime 2: Echoes

Much like Bloat, the most difficult boss in 2004's Metroid Prime 2 isn't one of the final bosses of the game. That title actually goes to the Spider Guardian mini-boss, at least in the original GameCube version of the game. On the Wii edition, this encounter was a little bit watered down--but still hard. Unlike most of the rest of Metroid Prime 2's gameplay, Spider Guardian and other similar mini-bosses hold down the fort inside mazes that you navigate in your "ball form."

For the Spider Guardian fight, you have to avoid the boss and its passive damage field while it speedily navigates around the labyrinth. In contrast, you're just a stupid pinball that has to painstakingly jump around the maze and try to drop bombs in the spider's path. This sounds fairly simple (if awkward), except that you also have to perfectly time those bomb drops if you want them to actually damage the boss--and there are four freaking phases of this bullcrap you have to get through.  It definitely takes a lot of practice to get through this one, but this short guide may help you figure it out a little bit faster.

Fontaine - Bioshock

Some people might disagree with me on this one. In the overall scheme of things, neither 2007's Bioshock or the boss fight with Fontaine are particularly notorious. However, I think Fontaine deserves a spot because the fight with him offers up a significant difficulty jump right at the end of the game. After you finally corner the duplicitous Fontaine, he injects himself with some gene-altering material (called "ADAM") that turns him into a superpowered monster, a la X-Men. His new powers make him a pretty terrifying foe, especially when compared to the rest of the game. Fontaine is lightning-fast, and his quick attacks give you very little room to defend yourself--let alone strike a counterblow. Even worse, there are multiple phases of this intense battle with no opportunity to save during it--and no nearby resurrection points if you die.

If you somehow manage to bring his HP down far enough, he'll be returned for a few moments to a recharging station--where you'll have to stab a syringe in his chest and try to drain out some of the ADAM that gives him his powers. Don't linger too long, though--he will soon break free and start attacking again with a different set of moves. You have to keep this pattern up until you successfully drain all of his mutant juice (it should take three syringes) to defeat him. If you've been having problems defeating Fontaine, this excellent visual guide might be helpful (it does contain some spoilers at the end, though!).

The Nameless King - Dark Souls 3

Okay, I know I said I was picking just one Dark Souls boss--but I can't really leave this one out. In 2016, Dark Souls III was released, and it offered up a whole new slew of insane bosses in keeping with the franchise's tradition. Among these, I think The Nameless King stands out above the crowd as one of the toughest boss battles of all time. The Nameless King is an ancient god of war who rides a storm drake and carries a lightning-charged spear into battle. During the first phase of the fight, The Nameless King is mostly airborne and you have to focus on taking out his dragon while avoiding the King's long-reaching attacks and gouts of flame from the drake. Another big factor in the difficulty of this fight is the camera angle; while on his dragon, The Nameless King takes up essentially your entire screen. This complication and the mist-covered ground make it hard to see, let alone dodge incoming attacks. 

If you manage to bring down his mount, The Nameless King will put the beast out of its misery with his spear--absorbing some of the drake's powers. Phase two begins, which is even more difficult. Much like Ornstein from Dark Souls, The Nameless King is very fast and can impale you in a heartbeat with that spear--each swing can easily wipe out 50% or more of your HP. If you get too far out of melee range, he also can call down lightning from the heavens to just fry you where you stand. Here's a pretty comprehensive guide to beating The Nameless King with some different strategies based on your character class.

Lord Kazzak - World of Warcraft

Back in the early days of World of Warcraft, it used to be possible to kite outdoor raid bosses pretty much anywhere on the same continent. Once players figured this out, a few promptly started a new trolling tradition that would go down in WoW history: taunting the raid boss Lord Kazzak from his spawn point in The Blasted Lands all the way to the Alliance capital, Stormwind City. In retrospect, that act alone is impressive: the trip to Stormwind probably took at least an hour, all while keeping Kazzak on your heels and managing not to die. Once they got the demon lord to Stormwind, they turned him loose among the players and NPCs in the city. Lord Kazzak had a passive debuff that healed him 25k HP anytime it damaged someone, and he got instantly healed 70k HP anytime he killed a player or their pets/totems. After a short while, he started spamming gouts of Shadowbolts in all directions.

Basically, this meant that Kazzak became invincible within a few minutes of reaching town. Literally thousands of players and NPCs must have fallen to him during that time period, and even those wielding legendary weapons couldn't bring him down. Kazzak's terrifying rampages would sometimes go on for hours, until a GM finally showed up to despawn him entirely. Blizzard eventually got tired of the issue (and player complaints), and wrote a patch that chained outdoor bosses to their spawn points permanently. This may be cheating a little because he's no longer a playable boss, but I will always count Lord Kazzak's little Stormwind vacays among my craziest WoW memories.

Yellow Devil - Mega Man

This boss ties with Mike Tyson as the oldest on my list. Yellow Devil was the penultimate boss in 1987's Mega Man for NES. Unlike many of the other bosses I've mentioned, Yellow Devil doesn't have insanely overpowered attacks or even multiple phases. No, this Mega Man boss is rage-inducing simply for the mechanics of his fight, which require extremely fast reflexes and a good sense of timing. Immediately after the fight begins, Yellow Devil splits into 19 fragments that race across the screen towards you before reassembling. If you're old enough to remember dial-up internet, it's kind of like watching a photo download a few pixels at a time--if those pixels could kill you. 

These pieces of Yellow Devil fly at you at different heights, and you must dodge and jump over them at breakneck speed and in the correct pattern. Get hit by just one, and the stun/knockback will usually mean the end of your run. Once reassembled, Yellow Devil shoots a bullet at you out of his single eye and then starts fragmenting again. He can only be damaged in that extremely short timeframe where he is whole, has already shot his bullet, and hasn't started fragmenting again. We're talking about a fraction of a second where he's actually vulnerable--and you have to dodge his attack while also getting off your own. No strategy guide for this one, it's just a matter of practicing it over and over to get your timing just right. However, if you want an easy way out, this video shows a bug/cheat that works for many people.

Duriel - Diablo II

If you've ever spent any time playing Diablo II, you'll probably agree that Duriel is hands-down the most enraging boss in the game. Not Mephisto, not Baal, not even the title character Diablo himself can top the frustration caused by the tanky maggot king that rules over Act II. This fat bastard is deceptively fast, he casts freeze spells that slow you down, and his boss chamber is really small. These factors combined make for a truly maddening boss fight where you are forced to scramble around just a few steps ahead of Duriel as you ineffectually try to launch counterattacks at him. If you don't manage to cast a Town Portal before he kills you, have fun on the loooong desert walk back to his location. 

He might be frustrating for regular Diablo II players, but those playing in hardcore mode truly understand why Duriel is called the "Lord of Pain." Death is permanent in Hardcore mode, which means many HC characters have ended their campaign in shallow graves at Duriel's chamber. Even worse, Duriel is notorious for the lag at the start of the fight. Oftentimes, you'll zone into his room only to find that you're already dead. If you're still struggling with Duriel, these tips might help.

Sans - Undertale

He looks like just a happy little skeleton, and Undertale's in-game info is quick to tell you that he is the game's "easiest enemy," but you really don't want to tangle with Sans. To access him as an enemy, you'll have to fully commit to the game's brutal "Genocide Route." If you do, you'll have to fight Sans as the final boss of the game, and he is ridiculously hard. In a way, Sans is a lot like Krusha K. Rool in Donkey Kong 64. Their boss fights are not similar in the slightest, but they both force you to completely discard everything you know about the game if you want to win. Sans turns absolutely everything you learned while playing Undertale on its head, and uses it all against you. He'll also steal the first turn and use some other pretty cheap tactics to try to win. 

Sans' description claims he can only deal 1 damage, but don't let that fool you, either. This actually means Sans can cause 1 HP damage per frame, which translates to 30 HP damage per second. You can't dodge, your attacks all mysteriously miss, and Sans will attack you through your UI and menu. If you actually manage to make it through his absolutely bonkers set of attacks, Sans will pull one final gambit: dragging out his last turn for nearly 15 minutes in hopes that you'll quit out of boredom. When you look at things from his perspective, it all kind of makes sense. You've done some truly evil things to get to this point, so maybe you're the final big bad and Sans is actually the hero of Undertale. Whoa...anyway, here's a really great strategy guide to get you started. 

Alma - Ninja Gaiden

As any self-respecting Ninja Gaiden fan will likely tell you, the fight with Alma in Chapter 9 of the 2004 Xbox reboot is possibly the hardest in the entire series. That's not to say the older Ninja Gaiden games didn't have hard bosses, but Alma is just on a totally different level. She's fast, agile, and extremely deadly. Watch out for her pink fireballs, which blaze across the room as they home in on your location. If that fails, Alma will just pick up huge pillars of stone to casually crush you or use a tractor beam to pull you in and smash your face on the ground. The space you fight her in feels large--it is a cathedral, after all--but Alma actually gives you very little room to maneuver.

Alma's fight also appears in later ports of the game: 2005's Ninja Gaiden Black and 2007's Ninja Gaiden Sigma. In Black, Alma gets a couple of demon sidekicks to help out (not that she needs it) and can shoot more pink fireballs at once. The demon lackeys were dropped for Sigma, but the horrible camera controls for this PS3 version of the game are nearly a boss fight all on their own. No matter which version of Alma you battle, it's probably going to end in a lot of frustration until you finally get the hang of her fight. Here's a strategy guide with some good tips. 

Absolute Virtue and Pandemonium Warden - Final Fantasy XI

As I started with a Final Fantasy boss, it's only appropriate that I end with two more: the mega-bosses Absolute Virtue and Pandemonium Warden from the MMORPG Final Fantasy XI. Absolute Virtue was first introduced into the game in 2004. Guilds struggled for years to find a viable strategy for defeating it, because every time someone succeeded the game developers would patch Absolute Virtue to remove "bugs" (and that method of beating the boss). Flash-forward four years, and players still didn't know how to beat it. In 2008, Square Enix ended up releasing a vague "hint" video showing some devs beating Absolute Virtue--which was completely unhelpful to players. One lead FFXI employee estimated it would take 18 hours or more for a guild to take down Absolute Virtue. Yes, really.

The next FFXI megaboss to be released--Pandemonium Warden--was just as bad. In 2008, a top guild battled Pandemonium Warden for 18 hours straight before giving up. They fought the boss through twenty different stages without taking any breaks, and had to end their attempt when players started getting physically ill. One player in the guild estimated that finishing off Pandemonium Warden would have taken another 2 to 5 hours. Two weeks later, Square Enix finally responded to player outcry over these bosses and drastically watered down the difficulty of both Absolute Virtue and Pandemonium Warden. They also set a 2-hour limit that forces the bosses to despawn if a battle drags that long. Even with the changes, it took another five months before a guild finally beat Pandemonium Warden for the first time. Although you can still play FFXI in 2018, I'm not including a strategy guide for these two--the change in player level caps has made them all but trivial encounters today.



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World of Warcraft alone would be worth a top list of most frustrating, yet most rewarding boss encounters. I just remembered Blackwing Lair back in the WoW Classic days, when it took us more than 100 tries each for the first two bosses (Razorgore and Vaelastrasz). 40 raid/guild members staying up all night, rezzing over and over again.

Oh, no kidding! My "toughest" classic list has gotta be AQ40, getting attuned for Kara (ugh black morass!!), actually running Kara, and getting killed so many times by the elevator in Coilfang reservoir (technically BC and not vanilla but close enough). Thanks for reading!

WoW required players to have some nasty skills those days. Now everything is just mechanic, you can do anything you want with just one or two addons and lacking the proper skills.

It's definitely easier and more accessible these days, but I think a lot of the changes have been for the better. Learning talents from a trainer, leveling up weaponskills, and other things like that were just a lot of grinding. Blizz is a lot better about offering new and exciting content (even between expacs) to keep people interested and having fun. I remember in BC when we spent months bitching about the wait for Wrath, it took a while before they finally added the Isle of QuelDanas to shut us up. They seem to have a better handle on the amount of time to wait before adding new content, these days.

I personally like it better until BC, after that the game grew in it's story, but some things just stopped to appeal to me and after wrath I just lost close to all interest (besides as I am from Venezuela it became nearly impossible to continue paying the monthly fee)

If you ever decide to come back, look into the WoW token system. Basically it's a token you can buy with gold that is worth 30 days of gametime. The price is set by Blizzard, and it fluctuates but averages around 100k on my server at least. My husband plays enough that he's pretty easily able to pay for tokens for both his account and mine just with the gold he makes selling trade mats and other stuff on the AH. I don't think we've actually paid real money for our subscriptions in several months.

Talking about skill and AQ40, an old (2006) example of my former guild doing C'thun tries (sorry for the bad video quality):

I have a really soft spot in my heart for AQ40. The Paladin tier set from there is the first one I owned because our guild had it on farm after a few months, and it's just such a cool-looking zone. I still solo farm it occasionally, and can remember when I still had problems soloing the Twin Emperors. The fight with C'thun and the fight with Yogg-Saron (no lights) in Ulduar are some of my absolute favorites of all time. I think Ulduar was the last raid Blizzard designed that really captured my imagination. The raids in MoP and WoD were okay, but nothing really excited me about them. Some parts of Siege of Orgrimmar were okay, like the part with the water cyclone boss. Fighting Huolon? in the other MoP raid was fun too, the one that drops the floor out from under you.

I'm still leveling in Legion so I haven't tried any raids there yet. Got my demon hunter to 110 a couple of days ago, and now i'm working on my pally main.

I haven't returned to WoW yet. Maybe I will with the next expansion. Actually, I also liked playing Icecrown Citadel in WotLK. Especially, I liked to battle of the two flying ships, where destroying the other one was the task.

ICC is pretty great too, but I think I just got burned out on it after awhile because at one point I was running it on 3 characters a week solo trying to get the Invincible mount to drop. It is a good raid, though!

Thanks for sharing, some of these are definitely more frustrating than others! But a serious gamer should have no difficulty in eventually beating some!

Thanks for reading! The nostalgia bug hit me hard while writing this up, I'm seriously considering going digging in boxes for my old copies of Diablo II.

Sounds like an excellent time! Old is gold!

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I didnt know whitney and miltank was so annoying in the game too haha i need test pokemon silver and gold someday :) good post btw

Whitney is in HeartGold and SoulSilver too, but I think her Miltank's moveset is slightly different in that version. Except Rollout, it still has that--of course.

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Great read! Definitely some fun and frustrating bosses on this list from some really really great games.

Another great addition would be Orphan of Kos from Bloodborne. With it changing it's moveset 2 or 3 times thoughout the battle it made it difficult to predict, especially fighting him blind. Took me 2 dozen attempts or so to finally take him down! :P

Thanks for reading! That does sound like a great fight! I don't have a PS4, so I haven't had a chance to check Bloodborne out yet. Maybe this year!

If you get a chance I would definitely recommend it! I'm a big fan of Dark Souls 3 as well and it's a toss up which I liked more. :)

Man I totally agree with Alma (Ninja Gaiden) and Duriel (Diablo II)... Also, I did the Grazzak luring a few times myself, it was fun AF but I bet not everyone had hat much fun...
This was a really good post that made me remember those fun old days, thanks a lot

When this was going on, I was still a little baby paladin on Windrunner, probably didn't even have mounted training yet. I remember being in Duskwood or maybe southern Elwynn Forest when a group brought Kazzak through on their way to SW. I couldn't have been even level 20 yet, but I watched with fascination and followed (from a safe distance!) as they brought him into town. It was pretty hilarious to watch the players in town scurry away like a kicked anthill. Thanks for reading!

Wow what a fabulous read thankyou for sharing with us . I have followed and upvoted you , hope you can pop by and read some of my post , stay in touch x dee

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