Any game, any system, any time. Just make sure it's about what happened in the game. If you played something that caused a buddy to go shave his head and join a commune, that doesn't count. Add that as an aside, maybe, but this is the vidya board, son!
Glorious or god-awful. Serious or stupid. Rage-inducing or feels-inducing. Share yo' stories!
My first one:
A few days ago, I'm finishing playing my third playthrough of Dynasty Warriors 7 – Empires. I started as Lu Bu, got enough fame to rebel, stole Diao Chan as my wife and kicked Dong Zhuo's fat ass out of the ruler throne. (He later ended up as one of my subordinates. Why I didn't get the option to just kill him, and why he didn't try to take it all back, I don't know.) At this point in the game, I've steamrolled through pretty much all the other kingdoms. Only two more small ones remain in the south, both with two territories, Sun Jian's, and Meng Huo's.
Sun Jian decided it would be a good idea to try and capture one of my territories, cuz apparently he likes to throw his men's lives away. Needless to say, it failed and over half of his forces from the attacking province died. I could conquer that territory in my sleep. So I decided that now-Emperor Lu Bu would take a day off and let one of his other officers lead the charge. I chose Guan Yu, cuz dat beard. In this fight, I've got the enemy outnumbered about five to one. This means I start with all but two or three bases on the map and the battle should be over practically before it begins. There's just one itty-bitty problem.
I can't upgrade Guan Yu's weapons and he has the shitty starter ones.
Your character carries the army. If you struggle, they struggle. You bowl through the enemy, you'll crush them with only about 2% casualties. (This happened once and there's a trophy for under 10%.) DW characters attack power is pretty much dependant on having a good weapon. I had long ago maxed out my kingdom's weaponry level, meaning I could buy the fancy rapeface ones with elemental attacks, but apparently, that doesn't apply if I choose to play as another officer and I can't lend him any of mine!
What should have been a curbstomp turned into a struggle. Guan Yu barely survived after one of the enemies opened a dam and flooded the center of the map with him still there. (Surprisingly accurate to history.) He is unable to do much more than chip damage, even with his normally OP'd musou attacks, and his stats were just as high as the rest of my officers! I did eventually win with a sliver of health left and I took an embarrassingly high 37% casualities. I got the territory, but I learned to never trust my subordinates, even ones with the title "God of War."