Star Ocean 3/4 still has some of the most ridiculous trophies ever.

Do 77,777 Damage to super boss in one attack.

Halo is usually pretty difficult to 100%, you have a ton of achievements split across multiple game mods, MP, 2-4 player co-op, fire fight etc. Halo MCCs 700 achievement collection includes infamous achievements like Halo 2s Laso run which stands at a 0.04% completion rate on Xbox 😂 I have 545/700 and don’t plan on even attempting to 100% it, I actually don’t think I have the ability to even if I wanted to lol. 

I think the rarest plat I have is from a racing game (Sonic and Sega All-Stars Racing Transformed), but I don't feel like it was the hardest in comparison to some of the other stuff I've gotten.

I had a harder time on Trine 2 I think.

But the hardest plat that I tried to get but FAILED at getting?

Super Monkey Ball Banana Blitz HD. For me, that's probably the pinnacle of gaming difficulty. I don't think I'll ever be able to 100% that game.

Gears 2, a million kills

The ones that always irked me were the ones that involved online play. If I saw something like, get four kills while blowing up a tank, for instance, it was an instant "nope" lol.

I don't play enough console games or hunt trophies hard enough to form a comprehensive opinion, but I've noticed some sports games tend to have a lot of tough-looking trophies.

Games that force you to play a minimum of 2 to 3 playthru to get the platinum is a bit of a drag,

But if Ng+ is allowed while getting all your upgrades to get trophies makes the game fun at least

Red Dead from the poll but simply because it's so detailed and would amount to an insanely long experience. As for Racers, there's a Trophy in Porject CARS that has you fo a real time 24 hour race. The souls series are easy platinums if you are good enough to beat the game you won't have trouble getting the platinums, albeit they can get annoying as fuck looking for items, DS3 being the worst and not worth it.

The hardest platinums are skill based games, DMC: Devil may Cry the soft reboot was by far the hardest platinum I've achieved cause it took me to having to have perfect skill at the game on the highest difficulties, you can't power level your way through or take any shortcuts but rely solely on your own skill and the same with Sekiro as the odd bunch out of souls if you can even call it a souls like. You have to become skilled at the game or you're not achieving it. Thee hardest though, games like Super meat boy and the like where the odds are designed against you, you can't become skilled because it's trial and error based learning the whole way through, hands down the hardest to platinum and why so few have done so.

Oh and Divinity OS2, try beating that game on honour mode where it's the highest difficulty and you have one save I believe so you can't save scum qnd if your party dies your file is deleted in a 100+ hour game. I'd like to shake hands with anyone who has done that without exiting the game when things are going badly... hell, even if they did so it'd be congratulations worthy cause that'd be so frustrating. 

Oh, I'm gonna upgrade to PS5 before the end of the year and you mentioned double pops, is there a way to prevent this from happening if I want to play a ps4 game on ps5? Is it with all games. Will the platinum and trophy list just automatically fullfill once you boot the game?

Don't transfer the save file. That's how it recognises that you've already unlocked trophies afaik.

And I don't think it works with all games. You'd need to see which of your games would do this.