Yup. Two. PS2 controllers. One could have taken my TV with it.
One I was playing bloody roar two. Busuzima (who before then I NEVER had THAT MANY problems against) kept getting perfects on me. (And every fight before then, well, I was the one getting perfects.) Sometimes I would get CLOSE to getting a blow in but the time that broke me, I didn't even get a chance to move. I slammed the controller on the ground (I was on the floor) and it bounced hard, hit my knee equally hard... and ceased working.
PS2 controller number two I was doing a minigame in Xenosaga episode two. You had to be quick on your buttons an wash the windows in X amount of time and I believe you got a decoder key for a door that had a cool item behind it. I was easily hitting the buttons right, but the game didn't seem to register that. I kept having to sit there longer than I should have trying ot get Shion to wash the freakin window... but she didn;t... so I lost it and threw my controller at the TV. There was a spark, the controller's left army-thing shattered, and the TV went off. The TV still works fine, and my controller did for quite some time (A couple years) but it finally ceased working... Duct tape helped repair what was left of the broken arm but alas it only lasted so long... Which saddens me greatly... it was a blue glowy Pelican controller. That thing was beast (and it could light up my entire room.)