I'll throw my stab in at an unusual contender:
The Berlin Loveparade drew 1.5 million in 1999. While the various rave size sound systems were playing different sources for most of the event, it had been customary for all of the systems to turn into a special radio frequency for broadcast of a main stage at the siegesaule towards the end of the event.
maybe in the end it wasnt the biggest, but a bit unique.
In that realm, I thought I once read somewhere about a new years countdown in london which was supposed to cover millions of people.
hmm, going along that route, i believe the entirety of sweden is covered with a pa ready to broadcast emergency messages.