Late to this thread, but it did bring back some great memories! My first gig was so long ago that I'm not completely sure what it was, but it was with a band called "Proctors Gamble." I was probably a Sophomore in High School - the guy that started the band was a high school teacher in a neighboring town - thus the name. It was likely a wedding reception.
The most memorable gig was probably in 2003. My two sons and my wife are all musicians / vocalists and we took on a wedding reception in downtown Boston. The reception was large, the age span was wide but they all were on the dance floor shortly after we started. Many hours later the exhausted father of the bride was willing to pay us to quit so they would all go home! It was truly a magical evening. My kids are now too busy to play with their old man, but those were some good times! (Youngest son is the keyboard player for Ana Popovic - Oldest pastors a Church outside Orlando)