Not the worst but had some bad luck with Sleeping Dogs and Watch Dogs
Funny that both have Dogs in the title but I love dogs.
Sleeping Dogs buying all clothes but the trophy didn't unlock, used earlier save to get it again and didn't pop, gave up and year later got it on digital for like 5 bucks including DLC and play from scratch and finally got the trophy.
Watch_Dogs have that awful song search trophy, I spent like 12 hours trying to get the last song over two days but didn't find any and after that the game freeze and everytime I boot any game on PS4 it will freeze in 10 seconds, luckily changing the HDD fixed the problem. And then I continued to search the song and finally got it but guess what of course the trophy didn't pop. I had to play the game from scratch again after deleting the game data and save file.
The worst was Madagascar 3 game, it's not hard or anything but there's no guide for collectiblea and searching it myself gave me migraine.