My "worst gigs" weren't horrible in terms of technical difficulties or problems with the band being in sync, but they were definitely memorable. We still talk about them at times.
Once, while traveling to a gig, we lost the bass drum from up on top of the pickup truck! Some driver started flashing his lights, got us to pull over, and we proceeded to look for it, knowing even if we found it, it probably wouldn't be of much use, what with coming off a truck at highway speed.
We phoned ahead to one of our guys who lived in the city we were playing, and he managed to find someone at the college he attended that loaned us his bass drum. The show went on, albeit an hour late. On the way back after a 4 nite gig, we searched that stretch of highway in the daylight and never found a trace!
Then we had a gig in which I had a brand-spanking-new, PRS Singlecut Burgundy Tiger Eye 10 Top that at the time was the finest guitar I'd ever played. It was on loan to me for about a month from a friend of our bass player who headed up artist relations at PRS at the time. Everything I played on that guitar was just magic! But we were playing at the upstairs bar of a restaurant, starting at 9, and they still had dinner patrons downstairs who complained of the noise, mainly the bass & kick drum reverberating through the floor. Our drummer just hit hard, so even though we tried turning down, it was no use, and they told us to wrap it up after playing only 3 songs. I had so many friends/family showing up that night, some of whom got there after we were done, which
really sucked!
Then there was the gig where we could do no wrong. The place was packed, the band was on fire, everybody having a great time, but again, a restaurant/bar that stayed open after dinner, owned by a younger husband who
loved us, especially due to the large group of alcohol-buying, home-for-break, college kids that had heard us from the street and came in (from some nearby event that had just wrapped up), and an older wife who amazingly, just wanted to go home ("I'm
tired.") Some shit about not feeling comfortable with leaving her husband to close up. We had played our sets, but it was only midnight, and he wanted us to stay until 1:30, willing to pay us double, but she wasn't having it. So she essentially closed up a full restaurant/bar full of paying customers!