Decendents at Shepherds Bush in 2011. Not the biggest fan to start off with, it was the ex-wife who wanted to go, but it was an absolute shambles. Singers voice was shot, he stormed off after a few songs.
I've worked on some pretty bad shows. Some highlights include a band who shall remain nameless (a known band playing academy sized venues). Bassist had a heroin problem and passed out on stage part way through a show. He did the same the next night but we'd had the bassist from the support band practicing the songs and we literally swapped them over midway!
Once took a band all the way to Dundee for a gig one person showed up at, he got kicked out before they played for trying to start a fight with me.
Had a band who were with a massive management company and agent to play a midlands venue who clearly only had them there to not piss off the management and agent. Zero promotion and didn't even bother to book a support band. Played to a couple of people who had randomly wandered in off the street.
Another memorable one was a solo show by the singer of an 80s hair metal band. For some reason he had a one off show in York. Despite being British his entire band was American and he'd paid to fly them all in for the show. I could count the number of people in the crowd on one hand.