This is a tough one. Cloud's cross-dressing I feel is the most iconic moment, but on the other hand it's just a moment of the game. Chocobo Hot and Cold is grander in scale and pervades the whole game. It never reaches the highs of Cloud's cross-dressing but it provides a lot more substance. Storywise Cloud's cross-dressing is much better. It's a fantastic humorous episode whereas hot and cold hardly adds to the story at all. As a mini-game Chocobo Hot and Cold is vastly superior. Oh and then there's Triple Triad, well not that. Then there's the consideration that if I vote for the third place choice I might incidentally hand Triple Triad the win, which would be the worst. Have to think on it.