My greatest shame would be embarassing if I was alone, but it was made so much worse because I had an audience.
Back in early 2000s I was with several friends in one friend's house and we were playing SNES's Street Fighter. I think my friend only had one controller available that day because, different from our usual gatherings (where we would 2-play beat the hell out of each other), this time we were playing Story mode. We would each fight one enemy, two or three rounds, and whether win or lose we'd pass the controller to the next player.
It fell to me to take on Balrog (the boxer), which is most of the time a pretty easy adversary. Like expected I wiped the floor with him in the first round: I got a Perfect (zero damage to me, for those who don't know SF2 terminology ). Then the owner of the console pushed a new rule: whoever gets two perfects won't pass the controller.
I start round 2 imagining I will massacre Balrog. And I almost do, but he somewow got a hit on me in the middle of the round. Ok, I push him to the edge, then simply stop attacking. I let him win imagining I can get a perfect in the 3rd round instead.
I have trouble describing what followed. The 3rd round was a totally different fight. He came over to me, attacking nonstop, and easily avoided everything I threw at him. In just a few seconds I wasn't hoping for a second Perfect anymore, it wasn't even possible because I was already at 30% HP. I just wanted to get out of there alive. And even that was denied to me. I was utterly massacred by the most pathetic enemy in the game after letting victory escape me in the 2nd round by choice.
TheDudeLebowski: Desperados was indeed uncompromisingly difficult, which felt all the more more satisfying when beating it. I'm in the opposite camp: it's a favorite of mine.
Huh. I never thought Desperados was that hard... ok, there was one section I thought that. There's one mission in a Canyon where you have an extremely tiny window of opportunity to run and kill one enemy after another enemy turns away, and at the same time snipe a third enemy. But other than two or three cases like those it's perfectly manageable, you just have to keep slowly taking them out one at a time.