I worked from 19-29 for a company that specialized in throwing 600+ mass scale company picnics and whatnot a year nationwide. Needless to say, that made us very hard to please for our own picnics/party.
Every spring we would throw a massive bash that was family oriented and have pretty much every piece of equipment at our disposal set up as well as 20+ subcontractors giving us a freebie demo day to acquiant our sales force with the new offerings for that year. Were talking mass catering with 20 types of ice cream, cake, yogurt, italian ice, every conceivable type of meat and bread and crisps, soda, tea, beer, wine... carnival games, skeet shooting, laser tag, giant inflatable kiddie rides... you pretty much name it.
Every fall we would have the adults party. We would rent a large space like a brewery and have it as a total open bar and have a band play all night that was composed entiely of company staff. We would do any and all manner of cover tunes that anyone could think of. The playlist was usually linited to 50 songs. Our CEO was a total musician that could play about 50 instruments and his basment is a $250,000 recording studio/playpen. He would sing half of the songs and play lead guitar all night with his Paul Reid Smith. I did keyboards for the first 4 years but ended up being the audio/visual man thereafter. I hauled around some seriously expensive camcorders around for 6 hours taping everyone and everything whilst being as drunk as a lord ... not that anyone would notice as they were just as drunk.
This was all on a scale of about 300-400 people.