The first one I can remember was Merle Haggard at the horse track in Spokane when I was in probably 5th grade. It was pretty awesome, he was trashed, came onstage about 40 minutes late and then mumbled his way through a couple of songs before forgetting the words to Okie From Muskogee, he then stumbled off stage. While this would usually disappoint it made me really like outlaw country, and I still do to this day.