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Getting the 999 score on the donkey kong dual screen handheld in the early 80's figuring out the counter goes back to 000 on even higher speed gameplay.
That took me some time.
Same goes for saving the Princess in a platformer on the Msx2, sadly enough can't remember the name of the game.

Changing codes in Dos so my strippoker girls start their games undressed.

Experiencing FF7 and Squaresoft's quality for the first time.

The opening of Xenogears and Xenosaga. Fascinating.