I had a pub gig as a guitarist in a 4-piece band. Pianist and singer were going through the PA, and there was a full drumset. All I brought was a Vox DA-5 (Vox's equivalent of the microcube).
In my head, I had a dynamic mic and planned to put it on a wee tabletop stand next to the amp on the floor and mic it up, which is not ideal because I wouldn't be able to hear myself.
I can't remember why, but even that didn't work, so I spent the 2-hour gig playing riffs and solos to myself and the few people directly in front of the stage.
And after all that, at the end of the gig, I picked up my amp, flipped it over and remembered that it had a line out jack which I could have used.
Bonus fail: Singer forgot the words to a famous coldplay song (could have been fix you?), so the audience loudly sang the tune for her.
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I was 22
I stopped doing piano gigs not long after
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Supportact said: [my style is] probably more an accumulation of limitations and bad habits than a 'style'.
Problem was, after the soundcheck he had flicked the amp to standby without telling me. I don’t think I even knew standby was a thing at that point in my life. So come the first verse everybody else dropped out, and there was just the drums and me, except that I was silent. Not a good moment.
Don't play gigs on a farm.
Last gig somebody walked over a trailing socket and switched off half PA and my pedalboard. I scrambled for half the first song changing guitar cables before I saw the problem.