I've never had a crank come off, but I had one break:
My mother's partner gave me his bike to repair a puncture once, it had about 30 degrees of free play on the crank. He'd ridden it loose until the axle had chewed a lump out of the cotter pin, so that when he tightened it the nut just ran up against the end of the thread. From the vacant look I got when I replaced it, the improvement was lost on him.
I'm a bit baffled by this. Didn't the cyclist know they were getting loose?
My cranks used to regularly come loose until I started carrying a long 8mm Allen key... they spent a lot of miles feeling loose rather than just coming off all of a sudden.
It probably depends on whether or not the bolt falls out before the crank works loose on the taper. I went into the LBS to buy a crank tool once, the guy just gave me a blank look and said "What do you want
that for, we just take the bolt out and jump on the pedals until the crank comes off".