That One Boss...

[The Heik]

...that turns a usually-smooth game into complete insanity.
...that just appears out of nowhere and spikes the difficulty so high that you are left speechless wondering WTF just happened.
...that no matter how many times you played the game, makes you his ***** in the first attempt at defeating him.

We all have That One Boss. For me, that's Sephiroth in Kingdom Hearts 2. Never playing the arena area much in KHI, I never faced Sephiroth before. I just come to the end of Hollow Bastion, and this one winged dude is waiting for me. I recognize olde Seph immediatly. The boss battle then begins. I try to attack, he blocks, and one attack from him kills me. Just like that.

I tried time and time again, to defeat him I had to grind to lvl.99, go to a GameFAQ to see what were the most OP moves, and create Ultima by going back and forth to collect the Orchaluims+.

AND EVEN THEN THE SON OF A ***** TOOK 27 TRIES TO KILL.

You think Sephi in KH2 was bad? His prior iteration was even more of an absolute BEAST, mostly because if you hadn't mastered each and every combat technique that the game taught you, he was going to make you pay for your laxity. He's especially dangerous compared to his newer version because you didn't get to use all the sweet movement tricks you get when you've levelled all of Sora's forms. Honestly, KH2 Sephi got so much more easy after I discovered that a high-level glide lets me skim around the ground and dodge 90% of his attacks with impunity. He was still a ***** to fight, but it was at least manageable after that point.

 

[Sack of Cheese]

Conan's last boss on Hard. That son of a virtual mother, he made me wanna hurt cute puppies!!
Also: Shao Kahn! SHAO KAAAHN!!

 

[Mossberg Shotty]

Have you played the DLC by any chance? It actually manages to make the Sif fight even sadder, which is saying a lot, really, since you are literally killing a wounded, limping dog by the end of the fight. When he swings his sword and then falls on his side, kicking his legs helplessly, I just feel really, really bad.

No, I haven't checked out the DLC yet, though I was planning to until someone told me that it was gonna alter some aspects of PvP that I would rather it didn't. I figured I would just wait for the second one to come out to scratch my Dark Souls itch, but I'm still kinda curious what happens in it, especially now that you've mentioned the Sif thing.

Ceaseless Discharge is so annoying. It's almost impossible to defeat him properly (by atttacking his arm when he smashes it down), and I can never manage to lure him into the pit near the fog gate. He just stands at a distance and spams the unblockable, instant-kill fire blast attack at me.

I'm kinda glad I didn't find out about the exploit that kills him by making him fall, cause it sounds like a pain to lure him into it. If it helps, the way I killed him was by decking my character out in fire resistant gear. It goes along ways toward winning the fight, you'll still take damage, but you won't get knocked down as much.

 

[bug_of_war]

Terramorphus in Borderlands 2. I played the Borderlands series single player so I always prepare to get flanked and butt fucked by enemies coming in waves. And god damn it, this fucking Thresher just bends me over and rapes me into oblivion. I first faced him as Zer0, and as I said he killed me quick. After 10 attempts at taking it down I came to the assumption that it must just not be possible as Zer0. So, I tried my hand at fighting it with Axton, figuring that I could use the dual turret rocket launchers to distract and damage the asshole. How wrong I was. The bastard crushes the turret before it can even take away 1/16th of it's health and then all the attention gets focused on me. Fuck you Terramorphus, and fuck you Gearbox for making me fight an enemy like that in open terrain.

 

[Callate]

Seth from Street Fighter IV. Teleport, grab, oh look you're dead. Repeat ad tedium.

I may not be the greatest fighting gamer in the world, but good Lord, man. On a modest difficulty with a preferred character I can get through everyone else without using a continue, only to get wiped a dozen times in a row by Seth.

 

[tonka7794]

that one boss for me we all know and love him nemesis from RE3 never stops kicking my ass. Its like watching that one movie you always jump at that one part

 

[Ix Rebound]

Shao-motherfucking-Kahn
This douche-bags got more health than kintaro, more speed than kabal, and more bullshit moves than noob saibot and spams moves faster than the road-runner on a caffine rush

Your x-ray moves are about as effective on him as a flys fart and if you somehow beat him in 1 round and get him to half health on the second, the game will pull a massive "fuck you" out of its ass and pin you to the side of the screen and wail on you with hammers and kicks, both of which knock you down and leave you dazed until your dead

 

[Moralio]

There are several bosses that made me pull my hair out and two of them are from the Megaman series.

Bass/Forte EXE. This guy has kicked my ass so many times in the Megaman Battle Network games that I've kept count and it was 2,000 times this asshole has killed me.

Another would be Omega Zero god I fucking hated this guy, he was the sole reason I rage quitted Megaman Zero 3 as a kid and when I heard the bastard is even tougher in Megaman ZX I said fuck that and never bought the game(managed to get Megaman Zero Collection and kicked Omega Zero's ass finally beating the game after 9 long years.)

Another would be Dark Link in Adventure of Link I finally got through that god forsaken dungeon, killed the goddamn Thunder Bird, and got the triforce of courage.

"BUT WAIT THERE IS ONE MORE CHALLENGE YOU HAVE TO FACE" the game said as a shadow of Link appeared, five minutes later I was killed and had to start the whole thing over again cue five minutes of boiling rage.

The next day I beat him by exploiting that glitch where you stand at the edge of the screen and crouch stab since Dark Link can't hit you and completed the game.

I heard beforehand that Sephiroth in KH2 was difficult so I prepared beforehand, got best weapon, maxed all skills and then I one shotted him at about lv 65. Then again Seph in KH1 took me at least 10 tries to kill...

 

[Ghaleon640]

Its been a long time ago, but there was some big boss near the end of Bomberman Jetters. I hit him in every spot, at every moment of its animations, I've searched every spot on the map... can't hurt him. I was too stubborn to look online and I sadly haven't gone back to give it another shot since all those years ago.

 

[King Aragorn]

Shao-motherfucking-Kahn
This douche-bags got more health than kintaro, more speed than kabal, and more bullshit moves than noob saibot and spams moves faster than the road-runner on a caffine rush

Your x-ray moves are about as effective on him as a flys fart and if you somehow beat him in 1 round and get him to half health on the second, the game will pull a massive "fuck you" out of its ass and pin you to the side of the screen and wail on you with hammers and kicks, both of which knock you down and leave you dazed until your dead

That's not the worst part is. The worst part is when he taunts you and you miss that window by 0.000000001 seconds, and he gets his godly invincibility armor on, he hits you, and does hi 50% damage X-ray.

 

[Ix Rebound]

Shao-motherfucking-Kahn
This douche-bags got more health than kintaro, more speed than kabal, and more bullshit moves than noob saibot and spams moves faster than the road-runner on a caffine rush

Your x-ray moves are about as effective on him as a flys fart and if you somehow beat him in 1 round and get him to half health on the second, the game will pull a massive "fuck you" out of its ass and pin you to the side of the screen and wail on you with hammers and kicks, both of which knock you down and leave you dazed until your dead

That's not the worst part is. The worst part is when he taunts you and you miss that window by 0.000000001 seconds, and he gets his godly invincibility armor on, he hits you, and does hi 50% damage X-ray.

I swear to god, i don't know what netherrealms studios was thinking making him that OP
if it was just kintaro sized health and damage but a regular speed character that would have been fine

 

[King Aragorn]

Shao-motherfucking-Kahn
This douche-bags got more health than kintaro, more speed than kabal, and more bullshit moves than noob saibot and spams moves faster than the road-runner on a caffine rush

Your x-ray moves are about as effective on him as a flys fart and if you somehow beat him in 1 round and get him to half health on the second, the game will pull a massive "fuck you" out of its ass and pin you to the side of the screen and wail on you with hammers and kicks, both of which knock you down and leave you dazed until your dead

That's not the worst part is. The worst part is when he taunts you and you miss that window by 0.000000001 seconds, and he gets his godly invincibility armor on, he hits you, and does hi 50% damage X-ray.

I swear to god, i don't know what netherrealms studios was thinking making him that OP
if it was just kintaro sized health and damage but a regular speed character that would have been fine

It's keeping up with the tradition, I suppose. MK was always the mother of all cheap bosses, and that was upped by 10 in MK2011.

 

[Kikyoo]

Let's see... Tone breakingly hard bosses huh? well a lot of the ones I'm about to say might not be like that, but they are some ones that pissed me the hell off.

First up is Deviljho. O. My. . Just wandering around the elite ranked quests, Hunting down a peco. O how cute he summoned another monster. What's it gonna be Rathian? Jaggi? I'm sure it won't be to-whaHOLYCRAPWTFISTHAT I've never seen one of those before! I wonder how O sweet crap on a pop stick did that fucker just take out 80% of my health with one attack!

The Deviljho changes the tone of Monster hunter when you get into the high ranks. It's not enough to be able to escape him, you've got to deal with him being in your way. And he is REALLY strong. You don't get a quest to fight him till you've basically beaten the game. I enjoyed the change, found things more exciting, but this guy is at the top of my list of game changing bosses.

Dr. Wily. This guy is un-fucking believable. It's not until Megaman 4 that he really starts becoming a huge pain in the ass, with the wily capsule, but it's a trend that sticks around. That last encounter with Wily tends to be one of the most hair pulling, teeth grinding, wall punching encounters in the game... O yeah and special props to the Yellow Devil. I didn't have a problem with him, but any badguy who makes retro gamers piss themselves has to be mentioned.

I'ma just do one huge blanket one with All the Disgaea secret bosses. These guys usually out level you by a ton. 400-4000 is the general pecking order. These guys are seriously a huge wall to climb.

Zeromus from Final Fantasy 4. If I have to put one RPG on a list, this one is it. He's watered down in a few versions, but if you play either the original Japanese version, or the DS remake, this guy is unfairly powerful. Doesn't use a lot of tricks, he does have one or two, but his big thing is he will nuke the FUCK out of you. That's basically all he does is blow you up!

And now from my own personal hole of misery and pain we have Megaman Juno, from Megaman Legends. I don't know why this guy fucks me over so hard, but FUCK this guy fucks me over... HARD. Even when I know his attacks and how to avoid them, he still takes multiple attempts for me to beat. Even tho I've fought the CRAP out of him, and can beat the entire game barely taking a scratch... Why this guy? It doesn't make sense. Someone help me feel better about this by saying that Juno kicked your ass too! T.T

And lastly... Malroth from the original Dragon warrior 2. He can kill you in 1 hit. He can heal himself back to full health. He can get multiple attacks a round. He will fucking DECIMATE you, even if you are at the max level the game will allow he can still destroy you!

 

[GregerFisk]

The first boss in Deus Ex: Human Revolution. It was not only hard (especially when playing non-lethal), it was also badly designed and didn't fit the game at all.

 

[XSTALKERX]

Manus father of the abyss. Seriously Dark souls is a fair game but that one boss in the new expansion is almost impossible to defeat. The sanctuary guardian? ahh no he was cake walk, Artorias? nah just time your moves properly, Gwyn? just counter and you'll be alright. But manus, that ************ is the most impossible, cheap ass boss ever, I remembered looking at my watch the first time a fought him, it was around 10 pm, I managed to beat him at 2 fucking am in the morning. After that I never went back and played the expansion.

 

[Adam Locking]

Nobody's mentioned Benoit from Silent Bomber yet? Potentially the hardest boss-fight of the PS1 era, or at least the one that sticks with you the most. Only going back about 3 years ago, he still always managed to crop up in these sort of topics, and usually before the end of page 1!!

More recently, Virgil in DMC3, especially at the top difficulty levels, yellow orb mode. I can manage it on very hard with no items and an 'SS' rank, but DMD is still kicking my ass.

 

[Dragoon]

Uh there's this one boss in Persona 4 who literally turns around and bitchslaps you in the face in I think the third dungeon. It really spikes the difficulty, partly because Black Frost doesn't work against him. Black Frost is stupidly good in the second and third dungeons but he falls off hard after that, think Drake Sword in Dark Souls type falling off. Really good to absolute bollocks in a second.

Ok fine i'll name it but spoilers

Spoiler

Shadow Teddie if you don't realise who i'm going on about. Shadow Rise was deceptively manageable then BOOM FUCK YOU SHADOW TEDDIE IN YOUR FACE!

He is the one reason I had to stop playing Persona 4 for a bit, I lost to him about 5 times in a row and I got a little bit angry so I stopped. Next time I tried though I did him first time so the break served me well, it was pretty damn satisfying.

Recently it would have to be

Spoiler: Metal Gear Rising spoilers

Senator Armstrong's boss fight, up until that point I had been breezing through the bosses but then he came and ***** slapped me down a peg. I loved the challenge and the music though, one of my favorite boss fights ever and it was so satisfying when I beat his ass.

 

[Pink Gregory]

As difficult a fight as Ornstein/Smough was, it was a damned fantastic fight.

I'm not all that good at Binding of Isaac anyway, but the bosses that always, ALWAYS wreck my shit are Monstro II and Peep.

Fuck Peep. Maybe they're too fast for me.

 

[Mister K]

I don't know if this bastard qualifies as a boss, but Father Kolgrim from Dragon Age: Origins.

This shmuck killed me about 12 times before I changed the difficulty to easier one. Hell, even optional dragon boss in the same location and final battle were not as tough.

If not, then King of Fighters boss. No specifications, pick the one you fancy, because they all are overpowered as hell.
Still, Rugal is sooooo goood:

 

[AgentLampshade]

The guardians in Persona 3 are way harder than the main story bosses. So far, at least.