Top 10 Hardest Boss Battles of All Time

There are a plethora of difficult boss fights scattered throughout gaming’s history, but these are the hardest boss battles of all time.

Sephiroth (Kingdom Hearts)

Hardest Boss Battles of All Time

Near the end of the game, the Colosseum in Hercules’ world offers players of Kingdom Hearts the option to take on the Platinum Match challenge, a special boss fight reserved for the best of the best.

When they enter the arena, they’re greeted by a sigil forming in the sky from which a familiar a one-winged angel drops down. He stares silently at the player before unsheathing a massive katana, and then all hell breaks loose.

Easily one of the hardest boss fights in the series, the Sephiroth cameo fight acts as the ultimate test of the player’s skill and knowledge of the game.

Almost every attack Sephiroth sends out can decimate your life bar in seconds, and trying to use certain spells against him will have no effect at all or make him even more difficult to fight.

No one will judge you if you ended up passing on this fight and its admittedly minor reward, and for those who managed to overcome it, there’s little doubt they are decidedly skilled at the game.

Terramorphous the Invincible (Borderlands 2)

Hardest Boss Battles of All Time

After players have dealt with Handsome Jack and the monster he unleashes from the vault, one might wonder what their next challenge will be in Borderlands 2.

Sure, they could continue to wander the planet and finish outstanding side missions, but where is their next target to grind toward, and to unleash the utmost of their arsenal against?

The answer is, without a doubt, Terramorphous the Invincible, a writhing monster powerful enough to decimate even the most seasoned value hunters.

In addition to having a grossly large health bar and multiple forms with different status effects it can afflict players with, it is armed with several tentacles and attacks that come at the players in an endless barrage.

If it isn’t hurling boulders that inflict massive damage, it’s tearing through players’ shields with its spiked appendages. If those don’t work, then the monster’s laser tentacles will blast them from afar in what can feel like an assault from an army.

It’s not a huge surprise considering the mission it appears in is called “You. Will. Die. Seriously.”, but players who hope to 100 percent the second entry in the shooter RPG won’t walk away from this fight without using every single trick up their sleeve.

Steven Armstrong (Metal Gear Rising Revengeance)

Hardest Boss Battles of All Time

The story of Metal Gear Rising: Revengeance takes players to some pretty crazy places and pits them against some equally crazy and formidable bosses.

However, none could compare to Senator Steven Armstrong, the mastermind behind every war-fueling shenanigan Raiden has sought to end in his quest for revenge.

After his metal gear has been destroyed, he appears to be an easy target; that is, until he crushes Raiden’s sword in one hand, hurls him across the arena, and reveals he has enhanced his body with nano machines which grant him improved defense, reaction times, and impossible strength.

What follows is a battle that puts a player’s skills to the test, with every move making the difference between life or death. Every dodge has to be made within a split second of a hit landing.

Every parry has to be timed so that Raiden can escape the ensuing hail of blows, and every sliver of health taken from Armstrong must be carefully rationed so as not to trigger his counter moves too soon.

It’s a fittingly bonkers conclusion to a ninja hack and slasher set in the Metal Gear universe, but by the end of this fight, you and your frayed nerves will be happy to be done with this monster.

Dracula (Castlevania III: Dracula’s Curse)

Hardest Boss Battles of All Time

Castlevania is no stranger to difficult boss fights – in fact, we could write a whole list on all of the trails it has put players through over the years – but the final boss fight against Dracula in Castlevania III takes the cake.

After players make their way through every horror and abomination his castle has to offer, the blood-sucking count takes you on himself with a hail of fire balls and split-second teleportation.

Once players make it through this phase, they’re then greeted by a monstrous amalgamation of heads spewing venom and blood in every which direction.

If players manage to survive this, they then have to overcome Dracula in his most powerful form, towering over them as a hulking bat creature able to fire lasers in any direction.

It’s grueling, punishing, and more than enough to dry out players’ eyes as they try to make sure they don’t miss a single beat and get sent back to the beginning of the fight.

Luckily, the payoff is worth it, as no other boss in the series has a hope of giving you as much grief as this one does.

Sister Friede and Father Ariandel (Dark Souls 3)

Hardest Boss Battles of All Time

Marketed as the hardest in the series, Dark Souls 3 poses quite the challenge to players.

Not only does it return to the Estus Flask system of its first title, limiting recovery items to what the player can hold onto as they make their way through one hostile level after another until a bonfire is reached, but it also hosts a cavalcade of different bosses determined to rip out your entrails and send your soul to the great beyond.

And yet, after a few months, most had bested every challenge it had to offer, and were sure they could do the same with the game’s first DLC, Ashes of Ariandel.

Enter Sister Friede and Father Ariandel, the final bosses of the DLC and easily one of the hardest fights in the series.

Starting off as a solo fight against Sister Friede, who wields devastating speed and a razor sharp scythe, the battle transitions into a two-on-one brawl after she goes down, her father ressurecting her and then entering the fray to ensure an outcome in her favor.

Should players defeat them both, they then fuse into a stronger version of Friede, who now wields dark flame magic that stretches across the battlefield with every blow she launches at you.

No one would blame you if you had to take a break in between attempts at this boss, and fewer still would blame you for wrecking a controller or two… or ten.

Lou the Devil  (Guitar Hero 3)

Hardest Boss Battles of All Time

After making your way through the many gigs and cover tracks scattered throughout Guitar Hero 3’s story mode, you and your band are ready to strike out on your own and use the momentum of your popularity to rise to super stardom.

There’s just one problem: Lou, your manager, is the literal devil, and included a clause in your contract which stipulated that your souls belonged to him alongside your music and the profits from it.

Not taking this lying down, you and your band challenge him to a rock contest, with the more skilled walking away with all of your souls.

Normally, this would be the moment where you beat the odds, overcome the devil and reclaim your souls for an uplifting final accomplishment before the game ends.

Unfortunately, this only occurs after several dozens, or even hundreds of attempts, as Lou presents one of the most difficult boss fights in the series.

The higher the difficulty setting, the more precisely he hits notes and utilizes his star power, racking up a final score players can’t hope to equal if they make so much as one mistake.

It’s undeniably satisfying when you finally overcome him, but you’ll be feeling your hands and fingers throb for days afterward.

Cala Maria (Cuphead)

Hardest Boss Battles of All Time

Along with the fame it garnered for its rubber hose animation style, Cuphead earned quite the reputation for its difficulty.

Pitting players against boss after boss in an action platformer that would bring even old-school NES owners to bouts of frustrated yelling, it made it clear that only those with the patience and the skill to keep trying would see the end of its charming tale.

Where many hit what seemed like an insurmountable wall, though, was Cala Maria, a sea-dwelling medusa with a wide array of abilities that could grind players into dust.

Starting out as a siren able to summon sea creatures and ghosts of dead sailors, she adopts a different strategy after taking enough damage from the player.

This in turn leads to nearly screen-wide petrification attacks which freeze the player in place, many times just long enough for a volley of electric bolts to hit them from her electric eel minions.

Even if players manage to take down this form, it leads to a final chase wherein they have to wind and weave their way through a jagged coral passageway, still avoiding her petrification attacks if they don’t want to be torn to shreds.

It’s certainly possible to overcome her attacks, but that doesn’t make it any easier to get through that first time.

Orphan of Kos (Bloodborne)

Hardest Boss Battles of All Time

There’s something about From Software and crafting insanely difficult bosses for their games’ DLC. The final challenge players must face in the game’s The Old Hunters DLC, The Orphan of Kos is the antithesis of everything players have learned over the course of their playtime.

Erratic in his movements and a sponge for damage, he’ll have even the most experienced player on their toes throughout the confrontation as they try to decipher where he’ll try to strike, how quickly, and with what attack.

This only becomes harder in the second phase of the battle, where he unleashes electric and insanity-fueled attacks that can cover the entire screen.

If players aren’t careful, they could lose all their health to these moves in an instant, undoing every ounce of effort they put forth so far due to not reacting fast enough to his shrieks and tells.

To be fair, his end is a thematic one, revealing why nightmarish monsters descended on Yharnam in the first  and putting a suffering creature on the way to a reunion with its dead family.

Sadly, this was probably lost on players as they spewed expletives at the creature when it finally went down, so relieved it was finally over that they could care less what happens to it in the afterlife.

Mike Tyson (Mike Tyson’s Punch-Out!!)

Hardest Boss Battles of All Time

Picture this: You’re a young child in the ’80s who was lucky enough to get their hands on a Nintendo Entertainment System. It’s got all the latest games on it, not least of which the boxing game that everyone’s talking about.

You’ve struggled through countless bosses and memorized passwords so that you can make it to the final confrontation with Mike Tyson, and even if he’s the final boss, you think what you’ve been through has prepared you for this moment.

And then your face gets caved in after only 10 seconds.

This is how many a player remember Mike Tyson, a juggernaut of a video game boss that still stands as one of the hardest of all time.

Armed with instant kill straights, devastating uppercuts, and a flurry of blows only the most practiced gamer could hope to dodge, his arsenal of moves puts the rest of the game’s competitors to shame.

His openings for hits are equally difficult to read, leaving mere fractions of a second for players to react and deal even a minuscule amount of damage.

Even if players somehow manage to survive his initial assault and land some hits, the only way to defeat him is to knock him out, with a decision always handed down in his favor.

The payoff for defeating him is great, but that doesn’t change the fact that it’ll cost you a fair bit of time and sanity.

Pandemonium Warden (Final Fantasy XI)

Hardest Boss Battles of All Time

You know you’ve made your boss a touch too hard when it can’t be beaten in under 18 hours and taking it on causes players to become physically sick from the ordeal.

This was the case when Square Enix released the Pandemonium Warden on players of Final Fantasy XI after its original hardest boss, Absolute Virtue, was finally felled.

Unlike its predecessor though, the Warden was host to arguably impossible buffs and abilities that made it near impossible to so much as scratch it.

One guild attempted to do so for nearly a day straight, only for them to have to retire when several of their members reported they were experiencing physical ailments from trying to beat it for so long.

Square Enix later patched the boss to be less difficult, citing that they didn’t want to threaten the health of their players with a boss that posed such difficulty in overcoming, but it still serves as a foreboding ghost in the halls of video game history, looming over players as a boss fight so difficult it was deemed impossible.

That does it for our picks for the hardest bosses of all time! Which ones make your cut? Let us know down below.