Probably Monster Hunter World’s Fatalis. That’s the only fight I’ve ever had to genuinely grind for multiple days to beat. It was 100% worth it though, the feeling of bringing him down for the first time was unmatched.
Probably Malenia, but she’s beatable. Definitely had a tougher time learning her than Freide, Gael, Artorias, Manus, Fume Knight, or Ivory King etc.
For me it was Psycho mantis from Metal Gear Solid. The reason being that I didn’t understood English at the time, so it was literally an impossible boss. I got frustrated with it and abandoned the game, until I found a translated version of it and replayed it and he’s actually very easy if you know what you need to do.
Messmer the impaler from Elden Ring SOTE.
I love this boss, it’s not bs, just pure skill… Shame I lack any of it. Still beat him eventually.
Dunno if I ever beat Mike Tyson
Jake Paul, is that you?
Ornstein and Smough from Dark Souls. The series have plenty of difficult boss fights but this one is earlier than most and the biggest difficulty spike in the entire game IMHO.
Outside of the Souls games, there’s Lil’ Hunter from Nuclear Throne. I tried to beat this little trashcan SO many times and succeeded only once. It’s insane.
Also shout-out to Hush from the Binding of Isaac for almost giving me a heart attack when I was fighting it as the tainted lost. Never again.
For me, it was in Last of Us, >!when you walk through the door and get caught in the rope trap, then have to shoot the zombies upside-down.!<
I had to go through that entire animation over and over and over. It made me hate the game. I played a little bit more after finally making it through, but my heart wasn’t in it and I just stopped after a while.
Fume Knight from Dark Souls 2
MCP from the Intellevision version of Tron.
Great Wolf Sif because I can’t bring myself to kill a loyal pupper who is trying to save me.
Sword Saint Isshin is not the hardest fromsoft boss. IMO he’s not even the hardest boss in Sekiro. But he might just be the boss design GOAT.
Saving the VIP on Veteran at the end of Modern Warfare. I spent 4 hours, 4 HOURS trying to save that guy. Not a traditional boss but a boss nontheless
Maleficent in Kingdom Hearts 1.
Oh my god. I tried everything. Every potion combo, every magic combo, every adjustment of Donald and Goofy to make them heal or damage. Never beat her. And never beat the game.
And before that is the fight against Riku with that hours long unstoppable cutscene. “You’ll never take Kairi’s heart!”
I still have every single line of that “Kairi’s inside me” cutscene memorized, because it was so extremely long and was immediately before the hardest story boss fight in the game. I felt like I was throwing myself against a brick wall with how many times I had to retry that Riku fight.
In comparison, the second Maleficent (dragon) fight was a breeze. I spanked her in like two or three tries, max.
Most people agree that Hollow Bastion is where the difficulty actually spikes. Before then, most bosses won’t really give you any trouble as long as you’re properly leveled. But Hollow Bastion is what separates the “easy” section of the game from the “hard” section.
Having seen the game played, I know the difficulty stabilizes itself around that point.
The guy at the end of Hotline Miami was pretty tough.
For me it was Sword Saint Isshin from Sekiro. The ape already took me days to beat, but Isshin was weeks and hundreds of attempts. But it felt so fucking good - especially since it was easy to no-hit Genichiro by the end. God, he must have been pissed off.