One of my (now deceased) cats managed to break the spray bottle I used to squirt water at him. It doubled as the bottle I used when ironing and he saw a chance to take it out one morning when I was getting ready to iron my clothes. He knocked off the board and broke the trigger, the little turd!
To be fair, the "little turd" was practically inseparable from me from the time we got him. We actually had two cats that were brothers and both of them were unusually personable, sweet natured and not at all aloof. This guy was practically like my shadow though and always seemed to take getting in trouble with a "no harm, no foul, let's still be buddies" attitude.