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For me it's either Metal Gear Solid or Granturismo in '99. I can't quite remember which order but both were beaten early in the summer of '99 and many games came in quick succession after that. If it was GT it would have taken at the very least 12 months and if MGS it would be no less than 9 months. Before beating these games seeing credits was an impossible task, not just the skills of a nine year old but until the memory cards allowed for the saviour of progression it was a demoralising process going right back to the start. 

Did you manage to beat games before the advent of save data? Did you use some kind of password instead or did you just git gud?