Once, a band I was in was hired to play at an outside private party. But, when we got there and started setting up our electric guitars, drums, amps, and PA, one of the people who hired us said she was worried we would be too loud and asked if we could simply play without plugging in. Ooops!
Here's another one: my old band British Wire Gauge was trying to get to a gig but the old hearse jalopy we used to haul our equipment konked out on the way. Fortunately, my band mate Steve was a real handy and he managed to kick it back into very temporary life.
Most embarrassing moment was warming up for Chris Isaak at a gig in Oakland and comparing what he had on to what I had on.
My first electric guitar was a used Sears & Roebuck Silvertone with a terminally compromised upper E string. Fortunately, I managed to upgrade to one that I still play today - my red Gibson semi-hollow body D355. This gem of a guitar was also played by BB King, Jorma Kaukonen, and Jerry Garcia in his early Grateful Dead days.