Most bosses serve to test your mastery of a game’s mechanics while propelling the narrative forward. But there are some that are so difficult, so insanely unfair that you have to wonder if their designers secretly hate video games and the people that play them.

Although these games are pretty old and some of them are only available in arcades, most of them are also available on PlayStation, so if you want to try your hand at them, make sure to get some PlayStation Gift Cards!

Now, if you’re a sucker for suffering with a sweet tooth for pain, here’s a list of some of the hardest video game boss encounters ever.


Mike Tyson

Punch-Out!! (Arcade/NES, 1984)

Mike Tyson made his video game debut as the final opponent in Punch-Out!! As one might expect from one of boxing’s most dominant heavyweights, he’s built like a brickhouse and hits like a truck.

Big Mike has a variety of punches in his arsenal that can put you in a world of pain, but none is deadlier than his uppercut. In fact, one good punch to the chin is all it takes to drop you to the canvas. You’ll need to be quick on your feet and on top of your game to stay out of range of those knockout gloves.

The Mike Tyson fight in Punch-Out!! is a test in focus and endurance that will try the patience of even the most zen gamer. There’s no room for error if you want to take home the championship belt. Mess up once and he’ll send you back to Glass Joe to start all over again.


Ornstein & Smough

Dark Souls (PC/PS3/Xbox 360, 2011)

Many of the bosses on this list are here due to poor design — unpredictable patterns, ridiculous stats, impossibly fast response times. That isn’t the case with Ornstein & Smough, though. This infamous pair may be absurdly difficult to defeat, but they’re also two of the most fun characters to fight in all of Dark Souls.

Everyone remembers the first time they came face-to-face with the swift-footed Ornstein and his big-boned buddy, Smough. Up to this point in the game, all boss encounters were purely one-on-one affairs. Ornstein and Smough aren’t afraid to balance the odds in their favor, going at you in a two-versus-one battle that will test your mastery of Dark Souls’ mechanics.

There are ways to cheese this boss fight, but where’s the fun in that? Just power through, learn their patterns, and keep going. You’ll die a lot, but that moment when you finally succeed in taking them out will have you feeling like a god.


Ruby Weapon

Final Fantasy VII (PS1, 1997)

Weapons are super bosses in the Final Fantasy series that provide an extra challenge to completionists and masochists who enjoy a bit of pain. There are two weapons in Final Fantasy VII that are guaranteed to ruin your day: Ruby and Emerald.

While the Emerald Weapon fight is by no means a walk in the park, the Ruby Weapon will take you to a whole new world of pain. It has a high defense stat, deals a ton of damage, and brings a set of killer abilities that makes fighting it complete torture. One ability is particularly grief-inducing: it literally removes two characters from the field at the start of the fight, leaving the last guy to face the red-plated devil alone.

Beating Ruby requires lots of very specific preparation to counter Ruby’s natural strengths and exploit its elemental weaknesses. You also have to follow a very specific set of steps if you want to have a fighting chance, including going into the fight with two party members already dead so Ruby doesn’t immediately toss them out of the fight.



Final Fantasy IX (PS1, 2006)

Ozma is an optional super boss in Final Fantasy IX that’s the bane of JRPG completionists. While there are plenty of baddies in this game that makes its final boss look tame in comparison, Ozma is the most frustrating because you can’t grind your way to victory.

Ozma has a variety of damage-dealing attacks that can tear your party to pieces in just a few turns, including Death, which kills a party member instantly, and Doomsday, which deals massive Shadow damage to everyone on the field (including Ozma, but what a handy coincidence that Shadow attacks heal him!).

Even with a fully-leveled party, his Meteor skill deals a random number up to 9999 in damage to the entire party. 9999 is the maximum HP a character can have in Final Fantasy IX. Yup, one bad roll of the dice can wipe your whole team in a single turn.

There’s no brute-forcing this fight. The only way to beat Ozma is to spend several hours completing related side quests, collecting Shadow-absorbing armor, and stockpiling Status Defense items and gear. With zero research and preparation, you’ll be seeing the Game Over screen in seconds.


The General

Kaiser Knuckle (Arcade, 1994)

Imagine a boss so hard that they used to hold an annual event in Japan where players would try to beat him. That boss is The General, also lovingly (hatefully?) referred to as Bootleg Bison for obvious reasons.

The General is the final boss in Kaiser Knuckle (known outside of Japan as Global Champion) and he’s notorious for cheesing his way to victories thanks to a ridiculously overpowered move set. For one, he can teleport in your face and choke slam you to the ground in an instant. He also has a ridiculously fast sliding kick, which he spams constantly to box you into a corner before using an unblockable throw to stomp you in the face. Oh, and all of those moves have absurdly low frame counts, allowing him to seamlessly transition from blocking and countering to knocking your teeth in with no stops.

Remember that annual event we mentioned earlier? Well, that was last held in 2015 because someone finally defeated him in 2016. Just for reference, Kaiser Knuckle was released in 1994, so yes, it took more than 21 years for someone to beat The General.



Silent Bomber (PS1, 1999)

This action-adventure game from the late-90s blends the excessive self-seriousness of Metal Gear Solid with Bomberman’s explosive gameplay, and it somehow works. Gamers at the time didn’t appreciate this quirky fusion, and I’d dare to wager you’ve never heard of Silent Bomber until right this moment. Well, consider yourself lucky, because that means you’ve never had to suffer through the extreme cheese-fest that is its final boss battle.

Benoit is not only fast enough to avoid most of your attacks, but he also deals ridiculous amounts of damage. On top of all that, he’s extremely unpredictable, with an attack pattern that’s frustratingly difficult to get a read on. You’ll just have to hope and pray that his random movements will somehow land him on one of your bomb stacks.

What makes the Benoit fight so frustrating is that the game to this point has been a largely flat, straightforward experience. While occasionally difficult, Silent Bomber doesn’t even try to give you more than a mostly inoffensive, moderately challenging experience. The final boss battle makes you feel like you’ve been training for months for the Aggrocrag then suddenly asked to scale Mount Everest.


We hope you find this list of the hardest video game boss encounters handy. If you’re the type who loves a good challenge, give these bosses a go and let us know how it went. These are just some of the many bosses that have left gamers stressed and defeated over the years.

What do you think is the hardest boss encounter ever? Share your thoughts in the comments below.

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