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My top three Hardest Platinum Trophies are:

Rock Band 4
Red Dead Redemption II
Cuphead

Cuphead was probably the easiest of those but beating all the bosses quickly and without getting hit on hard mode was certainly a choice. Did it, though. got the DLC trophies, too. the 25 hours I spent on that was a fraction of what I spent on Rock Band and Red Dead.

Rock Band required some insane trophies. Doable, but VERY VERY hard going solo.

One trophy required you get 1,000,000 points on a single song. Even the longest song in the game, Rush's 2112, I could only get 750,000 points. I did do that online.
One trophy required a TRIPLE awesome on vocals which normally requires 3 people with 3 microphones, but if you're very good you can do it with one on a handful of songs.
One trophy required I get 5-stars on every song in the game on Expert difficulty. LUCKILY this could be spread out over all four instruments and few songs were hard on all.
One trophy required I get gold stars (near perfect scores) on 30 songs from the base game. Again, any instrument. did it on Guitar.

One trophy required me to get something called 'Locked In', an in-game achievement you can only get by getting perfect no-miss combos on 5 songs in a row in campaign mode. The 'locked in' achievement can ONLY be achieved in coop. You HAVE To play 2 instruments or more so I taught myself to sing and guitar at the same time. And get perfect on 5 songs in a row. Something that can only be done on a handful of 'sets' in the campaign mode. LUCKILY this can be done on medium difficulty, but you still have to get every note 5 songs in a row and not miss any song cues, so picking songs that can be done on an instrument and are easy to sing (metal songs, usually, don't have pitch requirements and you can just shout into the mic) is a challenge.

There are a bunch of 'grind out this much money' and 'earn this many fans' trophies on the campaign mode. Most of the trophies came pretty easily.

But there was one more potentially NUTS trophy in the DLC. Luckily it wasn't required for the platinum. Absolutely brutal. That means get the equivalent of gold stars (A near perfect score) in brutal mode. Brutal Mode makes it so that instead of seeing the full note chart cascade down the screen towards your fret board for timing, the notes disappear near the top of the screen and you have to remember where they are because you still have to hit the right notes at the right time. It's basically forcing you to play the game blindfolded on the hardest difficulty and get 100% on a song. Oh....and in this mode you can fail. In the base game the default is that no-fail mode is turned on for parties and stuff. You can fail in Brutal Mode. you cannot turn no-fail on. Not like it matters; if you're gunning for 100% then I imagine it's not a song you'd fail at.

I did all of that. I'm not even that good at the game.

Red Dead took a lot more work and was more frustrating but to the average player it wasn't too bad. Lots of luck involved and lots of patience. the HARDEST trophy was 'Gold Rush' where you have to get the gold medal on 70 story missions. I....foolishly misread this thinking it was ALL missions so I was systematically replaying every mission to get the gold medal. SOME of these missions are absurd, like getting into a gunfight and coming out unscathed. As in, not getting hit. The rule isn't actually that you can't get hit, but functionally that's what it is because some missions have a 'beat the mission without using healing', and 'beat the level with xx% health or more' and they have to be done at the same time. Except dying and restarting a checkpoint counts as healing so if you don't do the ENTIRE mission from start to finish without getting hit, you can't achieve every requirement.

Some missions required you get 20 headshots. have 90% accuracy, etc. IT's all possible. I did it. but it's absurd in terms of requirements. One mission I remember was like 7 checkpoints long and one of them like 4 checkpoints in required you defeat one enemy without taking any damage. In a fist fight. Where he had a knife and even blocking meant you took damage. And you can't just overpower him because he has a knife. Basically I did that mission 50 times until I got lucky and tackled him before he took out his knife and I took him out. And every time I failed I had to do the whole mission over and over again which had absurd requirements front to back.

Fortunately as I said the trophy isn't as bad as I made it to be, which is why this isn't #1. Because you need 70 gold medals. There are I think 109 missions in the game. So those absurdly stupid missions I forced myself to do were optional.

There's also a tonne of luck and grinding. Filling the compendium (Documentation of every animal int he game) took me forever. Trying to find certain entries and finding perfect specimens and hunting them properly was like trying to roll three D20s in a row and all three got 20. Hard to find, even if you find it there's a slim chance it was 'perfect', and even if it is the chance of hunting it with the proper method and not missing your perfect mark by even more than a hair was TOUGH. well more like it just took forever.

Getting 100% in the game which is required for the platinum also had you get to level 10 in each of the different challenges. Like how in 'gambler' you had to win x many in a row or get four of a kind in blackjack. Some of those were skill based but most of them were absolutely down to absurd random chance.

Plus there was a solid 50-100 hours worth of grinding just in the online mode.

Dark souls I and III were also kinda crazy as far as the requirements were concerned. Dark Souls III in particular had you forced to go through the game 3 times to play for different countered factions to max out loyalty since you CANNOT do both factions in the same run through, and one of the rings you need to get required you to beat the hardest boss in the base game on NG+2. I didn't find the Dark Souls trophies THAT hard to get, just a lot of grinding and honestly not worth it.



My Console Library:

PS5, Switch, XSX

PS4, PS3, PS2, PS1, WiiU, Wii, GCN, N64 SNES, XBO, 360

3DS, DS, GBA, Vita, PSP, Android