Played outside of Fenway Park with a friend of mine once... wasn't that wild... only made one dollar....
When I was 17 I played on stage in front of my summer camp. As part of my guitar solo I finished with playing my guitar emulate orgasm sounds... It seemed cool and funny at the time. I also made a short film at the same summer camp where I walked around with my Jackson flying V and mini amp and asked anyone I could find if they would have sex with me if I played them a guitar solo. There was no sex expected for real of course, but I thought I was being hilarious at the time. And It was the first thing I was widely recognized for musically.
When I was a teenager I saved up for a long time to get a gibson flying v 67 reissue. Less than a year later I ended up selling it to afford a custom carvin guitar. I've always regretted it.