Oh yeah, LOTS of times. Let's see....

First one I can think of is when my brother stepped on and broke my Starcraft Brood War CD.

Second I can think of is my 10cc Alive album. It's their live album, obviously, and it's pretty damn good. But it's so old and so used that it skips a LOT now.

And if we're talkin' VHS tapes, oh dear LORD! Those things were so flimsy I fear touching them. First VHS tape I ever saw destroyed was in our really old player, like our first one, and it ripped the shit outta Barney the Dinosaur. More recently, like four years ago, I tried to watch Sonic the Hedgehog on my old VHS player and it ripped THAT up, and proceeded to break the DVD player that it was connected to. I hate and love VHS players at the same time and I really wished that I had a VHS player still D: