What's the worst forced failure trophy you've seen/tried to get?

[da-Noob123]

As already mentioned the 100 deaths in Alien Isolation was one tedious grind having followed a guide for a one run platinum, getting those 100 kills was brain numbing. 

 

Kingdom Come Deliverance has a few in the  base game and in the DLC. Virgin, Henry has a hard enough life as it is and to be celibate on top of it, I'm sorry Henry I'll make thus run a quick one. Merciful - basically except for one story mandated kill you can't kill anyone, how am I supposed to be a knight in shining armor if I have to run or hide behind others in every battle. Last but maybe most amusing, You Had One Job - instead of showing a gambler the error of their ways by getting them drunk and taking all their money,  you need to get blackout drunk with the gambler.

 

All I can think of right now but I'm sure there are others.