Difficulty-wise, The Lion King on SNES. This game shattered my childhood.
I could never get through the 2nd ostrich riding sequence in the 2nd level as a kid. The rest of the game was fine, though, once I used the level select to skip ahead. Turns out, it was because my eyesight was shit and I couldn’t even see the correct obstacles on screen (I was trying to avoid the branches, but no it was pink hippos and bird nests the whole time, so my timing on the double jumps was always off). Replaying the game a couple years back when Disney re-released it alongside Aladdin, I found it still tricky, but doable.
The game was fun to some degree, just required an unfair time investment. The final fight was a memorably bad experience though. I was like eleven years old when I made it to the end and swear I spent almost a full hour clawing at Scar before I figured out that I wasn’t actually doing damage.