I completely destroyed a PS2 controller. I haven't taken my frustrations out on a PS3 one yet. What sucks is one of my PS3 controllers crapped itself anyway. Oh well, I'm going to finally get a Dual Shock one at some point then.
It was that Punisher game that cost me my PS2 controller. I got to a boss level (against the Russian, I think) where I didn't have great health, but couldn't back up. I played it like 50 times and couldn't beat it. One time I got really close and he still won and I lost my shit. Anyhow, I ultimately found some cheese way to beat him through a glitch of sorts and went on about my business.
That Punisher game ruled btw.