Astaroth (the final boss) in Omikron. I played the game when it came out in 2000 but I was young then and couldn't beat him. Then I played the game again twenty years later and it was surprisingly easy to beat...
this post was submitted on 14 May 2026
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Minecraft ender dregn
Same. I don't really play MC to "win" it, just fuck around and make things
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Doc Ock in the OG Xbox Spiderman game... can't exactly remember which one (probs for ps2 too). But if you beat it, you know exactly what I'm talking about. I couldn't stand that fight
Pandemonium Warden from FFXI.
The fucking Chernobyl mission in Modern Warfare was tougher than any boss I've ever faced
Oh man I have such vivid memories of carefully placing every trap at my disposal so they were maximally effective and wouldn't destroy each other, then running between tiny points of cover trying to do whatever I could to survive the hail of bullets coming my way.
I think I was eventually able to beat it on the hardest difficulty a few times, but that console has been dead for a long time so no way to check.
Only way for me to defeat it personally was to abuse a glitch that made the enemies miss their grenades allowing me to stay in the same cover instead of rotating
Otherwise, I saw no way to do that. There's just no cover on that level.
The final boss in Cuphead (the Devil). I was very near the end, battling his last form... and my character glitched out under a platform. He couldn't hit me and I couldn't hit him. Softlocked! I uninstalled the game.
Mario & Luigi dream team bros.
Bowser, end of the game. He just fully. Healed randomly if I recall correctly. Online I did not find any help.
After a few tries I ragequit, it was infuriating.
diablo 2, fighting diablo with golems and no cheating or souped up gear. i was using the fire golem to self-destruct and summoning him again and immolation effect on diablo while trying to avoid him, dont know which difficulty though. i remember taking an extremely long time to kill him. i ran out of materials to use for the iron golem which had the thorns effect.
My most recent play-through of Half-Life 2: Episode 2 ended in failure because I literally could not get myself together enough to fight
... despite multiple attempts. I now can't bear to play it again because those warning alarms trigger my anxiety.Spoiler even though old game
the Striders.
For a while I was convinced that having moved the game between PCs might have triggered some kind of anti-piracy protection and the battle was rigged to be impossible... but it's more likely that I just lost the reflexes and timing to be able to pull it off. Especially since I own a legitimate copy and was playing through Steam.
A similar story is true of the final battle in Quake 4, which I barely remember now. Pretty sure I was still on Windows at the time and I've been on Linux for the better part of a decade. It was also from a backup and wasn't through Steam, but I own a legit copy of the game and there are no in-game alarms that I remember so that might be on the reinstall and replay list at some point. Maybe.
I don't play that many but I generally 100% games I play. So... a bit embarrassing, but Dicey Dungeons. The later chapters are genuinely difficult & are more puzzles than roguelikes... so I just gave up at one point
If specific endgame challenges count, I've never beaten Dead Cells BC4 boss rush, or the fabled Noita 34 orbs run (was very close though). Oh and every other rhythm game if you count skill analyzers/Dan courses, but most players don't clear those
Ikaruga.
Not necessarily for any particular boss - but I enjoy shmups (Gradius, Thunder Force, Gaiares) and getting anything other than a "c" on a level is work. I've even seen videos of people 2 sticking the game (playing both players at once) and getting S on levels...
Combo of the Thunderbird and Dark Link at the end of Zelda II. The dual SOBs were impossible for me and everyone I ever knew until emulators and ROMs made it possible to save state and jump back in over and over.
The Jaquio.
Pokemon ZA Zygarde has been kicking my ass. Usually I'm the one who dies while my pokemon are just fine.
Longest: Sister Friede Never: Absolute Radiance (mainly because I ain't playing all the way through the Pantheon to face him again)
When I was a kid it took me several years of owning TimeSplitters Future Perfect to beat the story despite playing it literally every day. Id first seen the game when I was younger and watched my older cousin play it and the zombie house freaked me out so much that it would get my panic going when I got the game myself at around 13. It wasn't until I genuinely set down with the goal of beating it that I realizes it had not aged well at all in the high point of the zombie craze and was actually hilarious.
Easily my favorite game of all time and I can't wait for TimeSplitters rewind to get to it. I still have my disk and of all things, the spot I used to stop it at is exactly where it throws a disk read error on my reclaimed Xbox.
it took me a stupidly long time to beat shadow trap in borderlands pre sequel as athena. probably hardest boss fight ive ever beaten
Starfox adventure final space boss. After taking months adventuring my way through the game the space fight suddenly ramped up. Had no idea how to beat him.
Friend came over barreled rolled instintvly (I had never played the originals). Blew my mind.
Not a traditional “boss fight”, but Tropical Drive Westbound on Burnout 3 has a time trial that requires you to go full speed in an F1 car for 4 minutes without crashing to beat the time. Absolutely one of the toughest events I’ve come across in an arcade racing game.