Skip to main content

The 8 hardest bosses I’ve beaten throughout my video game career

God of War Kratos Shouting
(Image credit: Santa Monica Studio)

Elden Ring has inspired me. Not because it's one of the greatest games ever made (even though it is), but because there’s a particular moment I can’t stop thinking about: The game features a boss that trapped me in one place for hours with dozens upon dozens of failed attempts to defeat them.

As the minutes passed and my number of deaths increased, I realized this boss was rising in the ranks amongst the hardest I've ever fought. All of those bosses, in one way or another, broke me. They challenged my fighting spirit and forced me to play beyond the very best I could.

To celebrate Elden Ring's release, along with one of its bosses making me realize that I'm nothing but a victim to FromSoftware's malicious will, here are the hardest bosses I've ever defeated. For the sake of diversity, I’ll only be including one entry per game.

Keep in mind, this list is based entirely on my own experience. Some of these bosses were incredibly challenging due to the difficulty setting I was playing the game on. If you want to avoid spoilers for Elden Ring, don’t go to the bottom of the list.

8. Harbinger (Halo Infinite)

Halo Infinite on Legendary is a nightmare. And Harbinger is a huge part of that equation, as the player is forced to battle a wave of ruthless enemies before the start of each phase. As soon as you make a mistake, you're sent back to when the enemies start spawning rather than when the boss re-enters the arena.  

Harbinger Halo Infinite

(Image credit: 343 Industries)

This means you have a very slim opportunity to learn Harbinger's attack patterns and how to avoid them. Every difficult boss forces the player to learn, and considering Halo Infinite on Legendary results in many hits being a one-shot kill, the player's already small time frame to learn about the boss is made worse by the waves of enemies you need to defeat to get back there. Couple that with an energy blast move that is very difficult to avoid, and you’ve got a boss who took me hours of retries to bring down. 

7. Date Masamune (Nioh)

While Nioh can be challenging, I never retried a boss more than a dozen times. But Date Masamune, a fierce dual-wielding swordsman who commands the elemental spirits of water and wind, uprooted my expectations of difficulty for the game. This foe is relentless, as his attack patterns are swift and he possesses plenty of brutal abilities. One move in particular has him charge towards the player, and if his katana connects, he will lock them in an animation that deals an absurd amount of damage.  

Date Masamune Nioh

(Image credit: Team Ninja)

And once Masamune begins imbuing his weapons with elemental power, parts of the arena become difficult to traverse as puddles of damaging water remove the safety of maneuverability. And even when he’s done casting spells, his swift strikes and far reaching attacks make it impossible to relax for even a moment. It got so bad that I had to farm healing items, which made failure especially punishing. 

6. Darkeater Midir (Dark Souls 3)

Darkeater Midir terrified me. After a stressful journey throughout Dark Souls 3, I was ready to complete the game and move on with my life. I was right at the end of “The Ringed City” DLC, prepared to take on the final boss when I found an obscure path hidden within an illusory statue. Suddenly, I’m plummeting down a never-ending hole as a colossal violet dragon slumbers on the other side of a massive chasm. I could tell my fight against this creature would not be easy, but I did not anticipate the hell I was about to be put through.  

Dark Souls 3 Darkeater Midir

(Image credit: FromSoftware)

Darkeater Midir broke me. I got so frustrated with my first five-or-so attempts against him that I tried to change my entire build. But the issue wasn’t with my character. The boss boasts a massive health bar and high damage output, with ridiculous moves that will make anyone shout in fear. One attack in particular encompasses the entire arena in a long-lasting flame. The player cannot run or dodge through it, and if they don’t come up with a solution, they will die. I could only defend against this with a shield, and even then, it always did massive amounts of damage. And although Midir boasts a ton of health, he will take a lot more damage if you’re attacking his head. This pressures players into getting up close and personal, rather than hovering around his legs. And when Midir begins shooting laser-beams that erupt throughout the arena, you’re going to want to go home. 

5. Ludwig, the Accursed (Bloodborne)

Bloodborne’s “The Old Hunters” DLC is well-known for its difficult bosses and unforgiving areas, but Ludwig in particular is notorious throughout the Bloodborne community for his relentless brutality.  Acting as the first boss of the DLC, Ludwig has way too much health, hits like a truck, and refuses to give the player a chance to attack. I spent hours bashing my head against a wall as I fought Ludwig, forcing myself to master every move he had under his belt. 

Bloodborne Ludwig

(Image credit: FromSoftware)

Ludwig will jump off screen and smash down on the arena, spew acidic spit, charge towards you with the speed of Sonic, swipe across the ground in a large arc, and smash his hooves onto the floor over and over to crush your bones. Even when the player thinks they’ve made decent progress through the fight, Ludwig transitions into his second phase when his health bar is at the halfway point. Many believe this phase is a lot easier than the first, but when you’re low on Blood Vials and have no idea what abilities he has in store, it’s going to be frustrating when a glowing blade of light kills you. 

4. Sans (Undertale)

Undertale is a critically acclaimed wonder that nearly every gamer knows of, and it features multiple playthroughs that result in novel experiences. Many fans go so far as to say that getting to end credits is only the start of the journey, as there’s much more to discover before seeing the full picture.  

Sans Undertale

(Image credit: Toby Fox)

While Sans is friendly towards the player throughout the other routes, he is a boss within the Genocide Route. Toby Fox knew exactly what he was doing when creating this fight, intentionally making it as daunting and punishing as possible. Plenty of fake-victories will make you put your guard down, and Sans continues to mock the player with every death. He will count how many losses the player has accumulated, offering a few new lines of dialogue as they fail more and more.

This battle starts abruptly with Sans using one of his most powerful moves against the player, and if they don’t expect it, they will die immediately. There is an extremely slim margin for error, and further in the fight, he will go so far as attacking the player while they’re selecting action within the menu. For shame, Sans.

3. Sigrun, the Valkyrie Queen (God of War)

God of War 2018 on the "Give Me God of War" difficulty is the single most challenging video game experience I've had. This setting is not only immensely hard, but it cannot be reversed once the player begins the journey. It took me three years to finally beat this game, and the ultimate crowning achievement was my battle against Sigrun. 

God of War Sigrun

(Image credit: Santa Monica Studio)

Sigrun possesses the moveset of every single Valkyrie boss in the game, and each one will nearly one-shot the player. You'll need to master the wind-up patterns seen in all of Sigrun's attacks, as they require exact reactions. Some need you to dodge in a specific direction, others require a parry, another one makes you avert your gaze, and sometimes Kratos needs to toss his handaxe directly at the boss.

Her powerful moveset is made even scarier when the player's room for error is so low. You will die in one or two shots, and the bossfight is long. Sigrun's health bar is the largest in the game, so players have to fight this marathon while making few to no mistakes.

2. Emma, the Gentle Blade (Sekiro: Shadows Die Twice)

I spent four hours and 30 minutes over the course of a week trying to defeat Emma. This isn’t just because the battle is difficult, it’s also related to that particular playthrough, one in which I did not take Kuro’s Charm at the start of the game. This meant that l received damage while blocking, enemies had more health, and my posture broke faster. 

Sekiro Emma

(Image credit: FromSoftware)

Emma has incredible range, unpredictable attack patterns, and uses a grab attack that can melt the player's health. But the difficult part of this battle doesn’t only involve Emma; once the player defeats her, Isshin Ashina appears behind Sekiro, holding Emma’s corpse in his hands. And as he unsheathes his katana, the player will soon regret choosing this ending. Isshin’s fiery geysers encompassed the whole arena and when I got hit by one, it often resulted in an instantaneous death. And beyond that, his attacks are swift and deal high amounts of damage. It took me so long to overcome this boss, and once I did, I screamed out of joy. 

1. Malenia, Blade of Miquella (Elden Ring)

Not only is Malenia the most challenging boss in Soulsborne, but she easily sits at the peak of difficulty throughout my time with video games. Her hellish mechanics evoke hopelessness, and toss the player into the throes of despair.

Malenia yearns for perfection. With every attack she lands on the player, she heals up a significant chunk of the damage dealt. The player cannot brute force their way through the fight with health recovery or powerful Ashes of War. Instead, you have to learn every one of her ridiculous attack patterns and figure out a solution against them.

Malenia Elden Ring

(Image credit: FromSoftware)

Unlike nearly any boss fight I’ve battled, mistakes result in more than just lost health. Now, the player loses valuable progress within the fight. There have been times where I began this encounter, landed six or so hits, and got skewered once, only to see all my progress lost and her health bar return to max. This is absurdly punishing, as it turns the slightest failure into a massive setback. If the player does not master her moveset, there is no way they can deal enough damage to beat her.

And the fun doesn’t end there. Malenia possesses a charge-up attack that is impossible to stop. You can’t run away from it, you won’t have enough stamina to block against it, and rolling through every single hit requires the mastery of a Street Fighter tournament champion. She lands dozens upon dozens of strikes in a flurry that can immediately kill you, no matter how much health your character has. Even after 100 tries over the course of four hours, I still cannot avoid most of this attack, even though I’ve gotten a little better at rolling through some parts of it.

To top it all off, when players land the final hit on Malenia, they’re rewarded with a cutscene. In this cutscene, we see Malenia bloom out of a scarlet flower, fluttering her wings as she exclaims “You will witness true horror.” Yep, the fight only gets harder from here, with a slew of one-shot moves and the rot status effect constantly threatening to whittle the player down to 0 HP. Good luck!

Self-described art critic and unabashedly pretentious, Momo finds joy in impassioned ramblings about her closeness to video games. She has a bachelor’s degree in Journalism & Media Studies from Brooklyn College and five years of experience in entertainment journalism. Momo is a stalwart defender of the importance found in subjectivity and spends most days overwhelmed with excitement for the past, present and future of gaming. When she isn't writing or playing Dark Souls, she can be found eating chicken fettuccine alfredo and watching anime.