Bitcoin used to have Silk Road which brought constant demand for bitcoins, we need similar things for Monero. I think non-kosher money is not the way we should engage actively but this type of projects like Risto's one.
Those projects, when successfully monetized, will bring large amounts of money (I am talking here about not millions but tens of millions, even hundreds of millions usd). If the game is done optimally and it is marketed the best possible ways. it might be a huge success and bring tons of non-crypto people to Monero-community.
Something that hit me today ... and this might be impossible to do. I think that either Edward Snoden or Wikileaks could see the value in an anonymous cryptocurrency. These seem like more legitimate causes that could benefit from anonymous currency than the blackmarket or
ISIS FundingIn the same breath - getting Snowden or Assange to advertise your anonomous cryptocurrency might be a tough thing to do. If someone pledged enough XMR to make it worthwhile to get a donate button on wikileaks it might work for advertisement (get picked up on coindesk, etc).
I'd feel more comfortable sending XMR than BTC to either of these projects ...
Edit: A "Download this miner and user your CPU cycles to support us" could also be an interesting social experiment. CPU coins allow you to support your cause financially with CPU cycles.