Worst gig? I got a million of 'em! Here's one:
The band I was in during the late 70's/early 80's in Memphis was a very popular local band. We'd get dinged to play all these parties/concerts whatever. Lots of the we turned down because the pay was like (an actual offer): "all the beer you can drink and all the acid you can eat."
But this one we took, they guy seemed really together, he was a good ol' boy from down in Mississippi, owned hundreds of acres of land, and was going to do a little festival with us and several other bands from the area. He was promising to pay us decent bucks, and it sounded like fun.
On gig day, we headed down there. Our sound guy was providing the PA for the whole gig as we had a huge system then. From what the guy had said, we were going to be out in the country where "nobody would bother us." We envisioned being on his land out in some field somewhere away from civilization, but when we got there we found out that while he DID own a lot of land, there were a lot of neighboring houses around. Turns out he didn't say a damn word to his neighbors about a thousand or so drunk/stoned/tripping rockers in close proximity to their homes! He had a beer truck out there and of course didn't have any permit for ANYTHING.
Anyway, by the time we got there a band or two had played and the band that was before us was just going on stage. The PA was crankin' and it was nice and loud. The crowd that was there was having a good time. So why, when we drove in were all these nice neighbor people lined up on the road shouting at us???
We find our host, drunk off his ass and hollering obscenities at a local cop, a real old guy, who was there in his car. We asked him what was happening, and he told me that they wanted him to cease and desist RIGHT NOW with the noise and the unauthorized party. He was a big guy and the old local cop was intimidated. I noticed the cop looking our way and talking on his radio. I didn't have a good feeling about this...
The band before us finishes their set, our stuff was almost set up (we actually had roadies, dammit!), and we were just taking the stage when 5 or 6 Mississippi state troopers come haulin' in with sirens wailing and lights blazing. We're standing onstage when our host goes out to meet the cops. I hear him shouting at them, then turn around and stalk toward the stage, the cops all following close on his heels.
He climbs up on the stage, and so do the cops. Mr. Drunk-ass host then proceeds to grab the mic and harangue the crowd, "These ****in' cops think they can tell me what to do on MY land! They want to shut down this good time we're havin'! I say, **** 'em all, I don't care if I go to jail," and pointing at us, "the BAND don't care if they go to jail we're gonna ****in' party!" We're back there shaking our heads "NO!!!" A state trooper near me points at me and says "you play that guitar, boy and you're gonna be in the back of my cruiser!" We slink offstage right about the time the good ol' boy starts trying to get physical with the cops, and they force him to "assume the position" and cart his still cussin' ass off to the pokey.
The remaining cops stand there and tell us to get our **** and get out RIGHT NOW, so we pack up under their watchful eye and beat a hasty retreat back to Memphis, just glad to be young and free! We never saw a dime from that one.