New York had a crack-down a few years ago against the street vendors peddling illegal copies of movies and music (you may remember the "Seinfeld" episode where Jerry is bullied into taking a video camera into a theatre to tape the film - one of the funniest of the episodes, but I digress). It was a response to pressure from the entertainment media to crack down on that sort of piracy. The NYPD shut down a couple of rings, but there were others waiting to move in on the now-open territory so I don't know if it was particularly effective.
Microsoft is fairly hard-core about pirated software, particularly their office suite of products, but for the most part have no way of catching folks in the act. I believe most of their tips come from disgruntled employees who report the incidents to MS, who then send investigators.
