Here's an interesting article about the Cannonball run. The idea of something like this fascinates me. I don't mean this specific type of illegal/disallowed thing, I'm more interested in the the type of action in general. I can't quite define it to my satisfaction, but I'll settle on this: activities that are disallowed by law (or moral, or ethical standards), would be disastrous if the whole country started doing it, yet have hardly any effect on other people/society/economy if only a select few do it.
Downloading movies and music is a great example of this. Back in the very beginning there were only a few people doing it, and the positive publicity that bands got by being able to share their music with more people quite offset the negligible lack of income. These days it's quite different, as almost everyone knows where to get movies or music illegally. Some might argue that this has become a serious issue, but I think it's still sustainable. There's still plenty of people who buy movies the right way. There's also plenty of people stupid enough to buy them on iTunes, so they'll have to repurchase them in some other store once Apple products go out of fashion.
The previous point quite clearly illustrates my viewpoint. As long as there is a risk of size X involved if you do A, only N percent will do A. And I think that's perfectly okay. This is how society should function. No progress can be made if we're all exactly the same. Or to put in machine learning terms: sometimes you need to deviate from what is 'optimal' to escape a local maximum. And the more people start doing X, the more obvious it is that it was the right choice from the beginning.
Sometimes the part that society is getting stuck on is clear to see, like with the example of downloading movies. There was a disconnect between prices of media and availability. Downloading things brought this to the surface. In the case of the Cannonball Run the local maximum isn't nearly as easy to see. Enforcement of road safety might be mentioned as key issue, with the raising of speed limits as a secondary, but there's lots of vague patterns of thought involved that would not have entered your mind if nobody ever did something 'crazy' like speeding a car all the way from east to west. It opens up your mind to new possibilities.