Great Wolf Sif because I can’t bring myself to kill a loyal pupper who is trying to save me.

MCP from the Intellevision version of Tron.

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!”

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.

Radagon and Elden Beast at rune level 1. The area of effect attacks and the tracking projectiles are brutal. I was able to get a strategy that clobbered Radagon in <1 minute without taking any hits but it required really intense concentration and timing. Not being able to practice just the Beast was the worst part, I hated having to slog through Radagon every single time to attempt it.

Also Sister Friede at level 1 is a strong contender. I don’t remember which took me longer to complete.

In Chrono Cross, when entering Time Fortress Chronopolis, you immediately encounter the PolisPolice. This isn’t framed by the game as a boss encounter, but it is.

There is a design problem with this boss that you probably wouldn’t see in a more modern RPG. To survive its big attack, you need the White Plate to absorb white-based magic attacks. You get the White Plate by stealing it from the Sky Dragon. If you already fought the Sky Dragon and forgot to steal at the time, you are hosed. The game doesn’t let you go back and redo that, and the PolisPolice encounter is about 2/3rds of the way through the game–very late to be starting over again.

I replayed that encounter 20 times before I finally lucked out on the attack cycle to keep the party alive. Then I encountered the actual hardest boss: a disc scratch that prevented the game from continuing towards the very end.

It’s been a long time since I played so my memory may not be totally accurate, but the final boss in fatal frame 2. I rage quit it because it was a one hit kill, and before you get to them, you had to walk down a long hallway avoiding other enemies. It was like 5 minutes of work to get to the final boss only for him to hit you once and you have to start all over. So infuriating. The rest of the game was so much fun.

Inner Agent 3 from Splatoon 2: Octo Expansion

What an absolute nightmare. They play like an online cheater. It’s just back to back sub and special weapons. There’s almost no room for error. I gave up after like thirty tries because the reward just wasn’t worth the stress and frustration.

Okay, i’m gonna name one that might raise some eyebrow.

Halflight, Spear of the Church from Dark Souls 3 Ringed City. I know i know, but i can explain. I’m doing a knife only, no summon run, i mainly use Brigand Twindagger for everything, and occasionally Bandit’s Knife for anything susceptible to bleed, and it’s quite a good run, beating anything with varying difficulty, and even Demon Prince were defeated with a knife, then comes Halflight, Weeb of the Church. Technically it isn’t a hard one because it’s basically vs an npc invader, but the difficult came from the constantly spawning Guardian that’s also do healing and also using a knife, and also the long reaching and parrying weeb sword of Halflight. I couldn’t get past this one no matter how much i try, it’s the most difficult “easy” fight i’ve ever did on this run, where the second most difficult one is…Deacon of the Deep.

So this is dumb but there is a Mummy game, as on the movie, I think on PS2. You could play through as either O’Connell (Brendan Fraser) or Imhotep (he was fun but pretty overpowered). I don’t remember there being a difficulty setting but I could be wrong.

I beat it with Imhotep but never could beat it with O’Connell. I want to say the final boss was the Scorpion King. I tried so many times.

The only thing I can figure is I didn’t load up on as much ammo, grenades, equipment, etc. as possible and never went back to try differently.

The striders towards the end of Half Life 2 episode 2.

Lavos. :(