The Most Brutal Boss Fights of All Time

Oh, boss fights. Those climactic video game moments we all love to hate. Or, maybe more accurately, we claim to hate brutally difficult boss encounters, while secretly reveling in the feeling of elation that comes when we finally manage to succeed. Below is our list of the 11 most brutal boss encounters in video game history, and our thoughts on why they're so much more nightmarish than your typical level-ender.

Mike Tyson - Punch-Out!!

So you want to be the best video game boxer? Well, Mike Tyson’s Punch Out!! was one of the few avenues for home console pugilists back in 1987. And the gauntlet to be the best digital boxer sounded completely do-able at first: Beat down 13 opponents in the W.V.B.A.’s Minor, Major, and World Circuits to achieve the ultimate in bragging rights. At least, that’s what we believed until the fabled Dream Bout with the top man of the heavyweight-boxing world at the time, “Iron Mike” Tyson.

Living up to the pedigree of Tyson himself, Iron Mike was unstoppable and his tells – a small (sort of) hint system most of the boxers on the Punch-Out!! roster had – were down right devious. Tyson moved with incredible speed and unblockable power. It was the kind of strength that stomped out any hope for so many would be champions from the late ‘80s to today. If Punch-Out was the story of Little Mac, the little guy who could topple a goliath, then Tyson was the unpredictable champion who had few weaknesses to actually capitalize on. - Jose Otero

Pre-Nerfed C’Thun - World of Warcraft

Gathering a large group of people to take down any boss in World of Warcraft is a tough challenge itself, but there were a few fights that were seriously harder than the rest. C'Thun, the last boss in the Temple of Ahn'Qiraj and M'uru in Sunwell Plateau both have a solid reputation for being so absolutely brutal that Blizzard had to nerf them to even the playing field. While these two are probably the toughest, Yogg-Saron, Hard Mode Mimiron, and The Lich King definitely gave me plenty of trouble over the years. The encounters are all incredibly different, but each test your raid members' ability to work together to simultaneously dodge, damage, and survive everything that's thrown at them. - Leah Jackson

Gill - Street Fighter III

Even for a company infamous for putting rage-inducing boss fights in their fighting games, Gill was a standout “eff you” at the end of Street Fighter 3. Sure, way overtuned damage, and “psychic” AI are par for the course when taking on a Capcom fighting game boss. But the cherry on top, perhaps the greatest bit of developer trolling in video game history, was when you finally, after countless attempts, fully depleted Gill’s health bar…only to watch him rise again with full health and keep fighting like nothing happened. Everyone who played SF3 remembers the first time this happened to them, and the controller they inevitably smashed afterwards. - Vince Ingenito

The Twin Emperors - World of Warcraft

The Twin Emperors encounter in the Temple of Ahn'Qiraj from vanilla World of Warcraft were the epitome of brutal. The encounter was so difficult, in fact, that the prevailing wisdom was that no raiding guild had any shot at completing the dungeon if they couldn't beat the duo.

First off, as the encounter's name suggests, there are two bosses with shared percentage health. You needed two tanks, which isn't in and of itself all that complicated until you factor in the fact that one Emperor is immune to physical damage and the other is immune to magic damage. Since warriors deal entirely physical damage, they had no way of generating threat on the magic immune one so my guild had to use a warlock, which back then was the tankiest (read: not that tanky) caster class. Positioning was key. The Twin Emperors had to be more than 60 yards apart at all times because if they weren't, they'd rapidly heal each other.

Every 15 seconds the Twins would Blizzard the raid, so you had to continually move, and every 30 seconds the Emperors would teleport to each other, wiping the aggro meter entirely, so prior to the teleport the whole raid had to stop attacking to give the tanks enough time to re-position and attack the bosses or else you risked getting one shot. Lastly, the Emperors had an enrage timer -- you had to beat them in 15 minutes or else they'd go into berserk mode and do 10x their original damage. There was no way to survive it so you had to finish in 15 minutes.

Getting 40 people to work together on a boss of this complexity, to be geared enough to do the required DPS, and to not lose focus and accidentally fire off an ability when you weren't supposed to was a nightmare for any raiding guild. My guild, in particular, wiped for weeks before finally defeating the Twin Emperors. - Sean Finnegan

Grim Reaper - Castlevania

Most early Castlevania games are grueling gauntlets of satisfying difficulty punctuated by instances of blinding agony. Chief among these nightmarish testimonies to masochism is the Grim Reaper battle from the original NES title. The horror begins just to the right of the boss platform, where two durable Axe Knights hurl projectiles while waves of Medusa Heads close in from both sides of the screen. Assuming you somehow survive this onslaught, you walk left to face a flying Reaper hurling scythes that cover most of the screen. Simon Belmont can endure only four hits and has the mobility of deep-frozen molasses. Avoiding the blades while dealing the requisite damage to the Reaper is akin to juggling six flaming chainsaws with your elbows stapled to the side of your head. - Jared Petty

Alma - Ninja Gaiden

Ninja Gaiden is infamous for its extreme difficulty. It demands perfection. It severely punishes mistakes. It’s downright mean. And there is no better encapsulation of what Ninja Gaiden is all about than the Alma boss fight.

What makes her so brutal is that there are no gimmicks or hacks. No simple patterns. Instead, pure skill is the only way to win. She is incredibly quick, requiring your dodging skills be on a hair trigger. Her speed also makes her hard to hit, making the fight a high-difficulty double-whammy. Just staying alive is challenging enough, let alone doing so while getting in some hits of your own.

Many gamers try to figure out Alma’s “secret” after dying against her the first several times. The horrible truth is that there is no secret. - Justin Davis

Giygas - EarthBound

When I think back on the most brutal boss fights I’ve ever tackled in video games, they share a commonality of forcing me to think outside of the box. In no battle is this as apparent as the final encounter with Giygas in EarthBound. The alien invader is initially completely impervious to any and all attacks that your party has relied on throughout their entire journey. No swing of a Gutsy Bat, barrage of bottle rockets, or hail of Starstorm makes even so much as a dent in Giygas. That’s when you get clued in to the strange truth behind this battle – the only way you can succeed is by using Paula’s easily-missed Pray ability. By collecting the positive thoughts of the various characters you’ve met along throughout the world, you’re able to finally put down you’re terrifying nemesis. - Marty Sliva

Absolute Virtue - Final Fantasy XI

One of the most frustrating boss battles of all time is Absolute Virtue from Final Fantasy XI. There's a lengthy process a group has to go through before he can even be summoned, after which the fight begins. He had a ridiculous amount of health regen, but if your party could make a dent in him it didn't matter, as he could simply use a White Mage's special ability "Benediction" to fully heal himself whenever he got low. Aside from the heal, he had access to every other special class ability in-game, and proved to be so hard that Square Enix eventually had to implement a 2-hour time limit on the fight. - Leah Jackson

Solidus Snake - Metal Gear Solid 2: Sons of Liberty

My first few runthroughs of Metal Gear Solid 2: Sons of Liberty gave me a pretty good idea of Solidus Snake. In short, I thought he was a bitch. Here's the President with crazy Doc Ock arms trying to horn in on Liquid and Snake's brotherly relationship. Lame. But when I set off to get every dog tag in MGS2, Solidus on Extreme Difficulty became my Everest. He was all that stood in the way of me polishing off my final dog tag run, and he was merciless. If you haven't played it, imagine using guns and C4 for the entire game and suddenly having a boss fight where all you have at your disposal is a katana. You need to block, dodge, and cut -- and you need to do it flawlessly on Expert. I tried over and over again in my college dorm room cursing again and again. When I finally beat it, I didn't even feel relief -- I felt respect. Solidus had gone from being a bitch to being a worthy opponent and an excellent end cap to the game. - Greg Miller

Ornstein and Smough - Dark Souls

You can’t talk about brutal boss fights without talking about Ornstein and Smough. The guardians of Anor Londo attack you as a pair -- probably because they’re too cowardly for a fair fight. One is quick and wields a lightning spear. The other is massive, and he crushes you with butt stomps and his oversized hammer. Once you kill one the rest of the fight isn’t too difficult, but getting to that point can be maddening. While you’re dodging Smough’s hammer swing, Ornstein will dash across the room and impale you with his golden spear. I didn’t break a controller during my 50+ attempts at the fight, but I definitely came close. - Brian Albert

Xemnas - Kingdom Hearts 1.5 HD Remix

Unknown Man (Xemnas) is the worst. Wielding two lightsaber-like weapons, he is incredibly quick and deals a massive amount of damage. Even with my Ultima Keyblade, he is damn near impossible. I haven’t beaten him, and I never will. Unless you are an amazing Kingdom Hearts player, you will not survive for 3 minutes. Besides Ornstein & Smough from Dark Souls, this is the only boss fight I have encountered that has made me physically ill from rage. And they say this game is for kids. Lulz. - Eriq Martin

The 11 boss fights above are responsible for uncountable curse words and broken controllers. But they're far from the only brutal video game boss encounters out there. Honorable mentions include Ruby and Emerald Weapon from FF VII, Tabuu from Super Smash Bros. Brawl, Sephiroth (in his Kingdom Hearts incarnation), God of War's Zeus, Street Fighter IV's Seth, The End, Ozma... the list goes on on and on.

Which boss fights have caused you the most anxiety over the hears? Leave a comment below and let us know.