Metal Gear Solid 2 on European Extreme.

Played when I was 8, and was stuck on fucking Vamp for like a year until I finally beat the cocksucker. Then I was stuck on the Metal Gear Rays for probably a good 6 months. Then when I got to the final Solidus choke scene before the final boss I just couldn't do it.

When I was 26 I bought an old PS3 and played the HD Collection and finally did it. And of course it wasn't too bad. Feels good.