That is to say, you're playing a tough game and failing repeatedly. You try, and try, and try again but the game is proving to be quite the challenge. But then finally, you do it (whatever it was you were trying to accomplish)! Only to have the game spit your hard-fought efforts back in your face and laugh at you because you're a loser!
I had one such moment earlier tonight. After watching Game Grumps play FTL - and having recently joined the PC master race - I decided to hop on steam and see how much it cost. Coincidentally it was actually the daily deal and was on sale for $4. I picked it up and started playing, only to find that the game is actually pretty damn tough. It's an incredibly fun challenge, though, so I keep at it. I managed to unlock the 2nd ship simply by making it to my 5th sector, and I've been using that one ever since because I like it's drone-based combat. Still, numerous attempts at making it all the way to the final star system ended in failure. But finally, earlier tonight, I make it all the way to the end! I've got full shields, 2 combat drones, one ship-boarding drone, a full crew all well-trained in their stations, a glaive beam cannon, a pegasus missile launcher, and a lvl 2 ion cannon. Time to engage the flagship!
I go and fight the big bastard and feel really good about my set-up. My boarding drone manages to land in one of the weapon rooms and takes out the gunner then the weapons system. My other combat drones are continually harassing the ship while my ion cannon is keeping its shields offline so my beam cannon can rip it to shreds. Sure enough, I beat the crap out of it! Or at least so I thought...
Turns out I just blew a chunk off the ship and had to fight it again. Well...alright, my hull took no damage in the first fight, so lets go finish that bastard off! I move to engage the ship again and immediately get swarmed by drones while getting hammered by the ship's three remaining weapons. It's a brutal battle, but I manage to overcome the odds and destroy......the right side of the ship. Now I've got 6 hits till I'm dead and I have to fight this bastard AGAIN?!
So yeah, seeing as how each stage in the final fight is greatly more difficult - despite the fact that I had utterly destroyed 2/3rds of the ship - than the one before it, I got massacred in a couple seconds. Yup, the game just spit in my face and laughed at me after I though I had finally beaten it.
So that's my (most recent) story, what are some of your Happy Gilmore Clown Moments?