Crash goddamn Bandicoot: The Wrath of fucking Cortex and the stupid Water Elemental Boss.
I wasted a week, before finally giving up, of my life along with a Controller which may or may not have deserved to be smashed to pieces for making me lose, because it was obviously not my fault. sarcasm, derp
Although I was like 8 at the time it still got me so frustrated I think I managed to explode the rest of my emotions, resulting in the apathy of the now. Thanks for that Crash, you dick.
Totally got my revenge at the age of 13 though when I managed to beat it first time through.
Totally worth the years of extensive emotional issues I got from that game..