Spelunky: Speedlunky
The whole premise to Spelunky is that the world you explore is randomly generated based upon certain biomes (cave, jungle, etc). Now, couple that randomized layout with having to beat the game in one sitting or using shortcuts to skip levels of the game. Doesn’t seem too challenging, right? How about beating the whole game in under eight minutes? This trophy is so hard to unlock that not even 0.7% of players have finished the challenge.