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.