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I had a few interesting ones, but one stands out in particular. A local dance band had booked two gigs on the same night and called the leader of our jazz quartet and asked us to sub for his group. No problem. We played a lot of standards, soft rock, and pop tunes so we felt comfortable playing for a wedding dance.

We got there and as we were setting up realized the gig was for a for a Greek wedding party and there was a good chance the a** hole who called us to fill in knew exactly what he was doing. The bride's father who hired the band was expecting a Greek Bouzuki Band that would play music to do "traditional dances" to---not a jazz quartet. On top of that, the last minute sub we got to play drums packed his set so quickly, he left his snare at home. We played a couple of slow tunes, but no one got up and danced, and the crowd began to get more hostile as they drank. The bride was in tears and the father who was a BIG man approached the bandstand with a look of rage on his face. How did we dare to ruin his daughter's special evening! Suddenly the piano player broke into "Never on Sunday", the drummer hitting a tamborine in his lap, and me reaching for my soprano. They began to dance and have a good time, but we had 2 1/2 hours left to play! We played Never on Sunday again, this time in a different key and it didn't seem to matter as long as they recognized the song and could do their dance to it. This went on for a while, as the piano player racked his brain to think of another song they might like that sounded---well foreign enough. The next seque was into Hava Nagila and they loved it! Over and over again all evening Never on Sunday and Hava Nagila were all that we played. Every word of this is true, you can't make this stuff up.
 

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Incredible! Good on ya!
Mine was about 45 years ago and not as much fun as yours. We were outside on a dragstrip (without cars). This particular song, Locomotive Breath by Jethro Tull, I was playing guitar. A drunk guy from the crowd wandered up to the band...no stage...and began talking to the bass player during the song. I rather aggressively suggested that he leave and as I lifted my guitar over my head he punched me right in the mouth! Didn't lose any teeth but there was plenty of blood. Needless to say, I was done. We packed up and went home...
 

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I've started this answer four times and I will get five sentences through, and I'll suddenly remember an even worse gig.
I had an awful experience in Bogalusa, Louisiana. I was playing with a fifties band fronted by a guy who wasn't picked for Sha-Na-Na. The guy had a huge ego. He had an agent, a couple of groupies and several hangers-on around him at all times. We were booked at a hotel out in the boonies. The band got through that gig okay before we put all of the gear back on the truck and went down the road to set up in a VFW hall that Mr. Ego rented. We were to play the next night and have a "[Band Name Here] Starring Mr. Ego Fan Club Appreciation Night" party. Three bucks to get in.

He bought radio time two nights ahead. He had his roadies put up signs all over the place.

Most gigs didn't start until after 9:00 pm, so while we were warming up, we expected to have some early arrivals.

Ten O'clock. Nobody's in the joint except the band, the agent, the two groupies, the roadies and the hangers on.

Ten thirty. Mr. Ego has his groupies stand on the street corners giving out beers to entice people into the VFW hall. We got a few people to go to the door, but they balked at the cover charge. We let them in anyway.

THEN Mr. Ego decides to have the girls tell people that it was free beer night. That got them in, but we ran out of beer fast, so Mr. Ego sent out for several cases of beer to placate the increasing crowd. Things were starting to get hopping when the sheriff shows up with the two groupies in the back of his car asking where Mr. Ego was.

It turned out that we needed a liquor license to serve beer. Even though the VFW hall served beer, its liquor license didn't extend to our Fan Appreciation Party because we only rented the VFW Hall.

Then there was the time that another group that I played with did a warm up for the Talking Heads and our guitarist's amp caught fire. The Heads' manager wouldn't let him use their equipment until David Byrne came out and talked with him. That was scary, but the gig went along alright after that.

Then there was the engagement with Mr. Naugahyde himself Ernie K-Doe (remember the 60's hit "Mother-in Law"?) when Ernie was too drunk to stand up, much less sing. That was fun.

Then the time when a manager (or agent) booked the band that I was in across the state and across several AFM Locals but didn't pay into the dues. We couldn't pay because we played in enough locals not to be able to pay up.

There are more. Like the night a fight broke out on the dance floor on one of the nicer clubs on Lake Pontchartrain in New Orleans. The horn section managed to get out of the way, but a couple of amps and mic stands got knocked over. The club owner didn't want to pay us for the time lost due to the fight.

I can't pick a worst gig. After those gigs I did mostly pick-up gigs with R&B bands.
 

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Back in the 90's I played and sang in a band that was a "Little Big Band" led by a Swedish dentist who sounded exactly like Hank Mobley and wrote all the charts out himself. Our leader was looking into purchasing a club in a town called "Woodinville" that was a mix of million dollars homes and farm houses. He and a Tap dancer friend asked me to take a look at the place with them before purchase. When we drove into the parking lot it was obvious we didn't fit in; 1) We didn't drive a truck 2) Our vehicle did not have a gun rack. Inside were line dancers and a Kareoke machine line up of the top country hits. Once back in the car the band leader and tap dancer were excited. They thought it was a great find. I voiced my concern but the leader and dancer were sure we could give the community a "Jazz Education".

Friday nights at this place had a big following. *This* was the night the food changed to a "Swedish plate with a shot of Absolute" This was the night our band took over. This was the night that all those trucks with gun racks pulled into the lot in expectations of line dancing and kareoke. I luckily was not singing that night, and was a harder to hit target. We found out the velocity of pool balls and shot glasses. It was a scene straight out of the Blues Brothers only *without* the chain link fence for protection. After a narrow miss by someone's scratch ball that landed in my instrument case, I put my horn away and excused myself. The rest of the band followed suite. As we left the drunks were screaming "Play some ****ing Rock and Roll". I wish I could end this story that I grabbed keys to someone's truck and did circle burns in the parking lot while shooting out car windows screaming "Jazz Rules", but the closest I came to that was telling someone who said We ruined *his* bar that he doesn't own the bar, pointed to our leader and explained that he now owns it and perhaps you should apologize. The Hank Mosley sound alike saw the money that could be made and returned the kareoke to Fridays.
 

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A night playing at the old Los Angeles Olympic Auditorium for roller derby maybe early 1980’s? What a freak show!! Oh, the gig went well, our band played great (loud-‘n’-fast Dixieland), and nothing went awry, but the CROWD! A total gathering of low-lifes just like pro-wrestling. Not a musically satisfying evening. DAVE
 

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Early 70's. We knew to not book fraternity gigs from University of Cinti, but one landed on the calendar. It was on the Johnson Party Boat that docked near the Riverfront Stadium on the Ohio River. About 30 min into the gig, with boat sailing down river, a fight breaks out & I wound up setting on the roof of the boat... sailing down river... for the next hour... in the rain... trying to cover my brand new MkVI... & didn't get paid.

When we docked, the rock band on the boat next to us was attempting to unload. They were all stoned & dropped a Hammond B3 into the Ohio River, completely disappeared

No more fraternity gigs.
 

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Discussion Starter #8
Early 70's. We knew to not book fraternity gigs from University of Cinti, but one landed on the calendar. It was on the Johnson Party Boat that docked near the Riverfront Stadium on the Ohio River. About 30 min into the gig, with boat sailing down river, a fight breaks out & I wound up setting on the roof of the boat... sailing down river... for the next hour... in the rain... trying to cover my brand new MkVI... & didn't get paid.

When we docked, the rock band on the boat next to us was attempting to unload. They were all stoned & dropped a Hammond B3 into the Ohio River, completely disappeared

No more fraternity gigs.
Next to yours, my worst gig was just an inconvenience. :)
 

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Mine was probably wind ensemble in a parking lot in southern California in the summer. No shade, few passer-by, no productive reason for doing this gig.
 

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In the late 1960's, we were hired to play for a wedding reception - at a Polish-American Legion Hall in South Bend, Indiana, following a Notre Dame home football game. Wildest, rowdiest, happiest crowd I've seen, but we were severely at risk. There was no stage, so we were at floor level. We had to lay folding tables on their side between us and the dancers to keep them from falling into us. Made for a long night!
 

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Mine was probably wind ensemble in a parking lot in southern California in the summer. No shade, few passer-by, no productive reason for doing this gig.
If you were wearing concert black, you win!
 

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In the late 1970's, we were teen age and were hired to play for a party for the end of year in a hotel:

The keyboard had failed just before the concert and we had to bring a vertical piano on three floors of stairs.

There was no stage, so we were at floor level an dancing people were putting firecrackers in the bell of sax.

At eleven the bass player was already drunk and wanted to go away.

And in the end our manager ran away with the van and our money,
 

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Golly, so many awful ones when I was new to the biz in the early '70s. Here are two:

1.) Acoustic band with three guitarists, a singer, me on flute. New-band tryout night at a dive bar in Berkeley. We warm up at the laundromat next door, then do our set at the bar -- actually on the bar, as there's no space for a bandstand. Nobody throws bottles, so OK. Next act to go on, one cat forgot to bring his guitar, so he borrows one from us & they start their set. Meanwhile, some hophead is harassing a barmaid, so the bartender emerges from behind the bar with a baseball bat & begins to sort him out. Our guy keeps trying to get his guitar back so we can split & avoid trouble, but the guy who borrowed it keeps playing & won't hand it over. The hophead's pals come to his defense; now it's a brawl. Suddenly the fighting stops. The barmaid has been knocked out cold. This could be serious -- turns out she has a metal plate in her skull from a previous injury, and as she lies there immobile, for all anybody knows she might be dead. In the general chaos, our guy grabs his axe out of the other guy's hands & we run out the back door into the alleyway just as a cluster of police rush in through the front door.

2.) Wedding trio playing light classics pre-ceremony as guests arrive. Finally everybody's in place & we get the signal to start playing the processional. We play... no bride appears. We play it over & over & over. Still no bride. We segue into another processional-type tune... now family emissaries are furtively running back & forth to where the bride is holed up. She won't come out. The groom looks like he can't decide whether to pee or vomit. We segue into a third processional & play it forever... then a fourth tune. Guests are out of their seats now, yammering; everybody's got an opinion. After about 20 minutes the bride comes out, crying (not happy tears), and goes through the ceremony as if she's the guest of honor at a firing squad. We got paid, but I still feel awful.
 

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I was sitting at the bar on a break from playing at a "Policeman's Ball" type gig. Sat down next to a policeman in plain clothes who was drunk & didn't like me sitting next to him, so he pulled out his revolver & put it to my head & told me to .... off. The place was filled with cops who came to my rescue & apologized for him. Good thing the next set was the last, since the set before the break almost was my last. I wish we could have opened the last set with "Shotgun" but it's only wishful thinking.
Then there was the gig where the bride's drunken father wanted all Polkas all night. We played our usual repertoire with a polka beat until the bride told us to go back to normal playing. "All Night Long" sounded great with a polka beat.
 

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The gig was on top of Mt Baldy (not Old Smokey).
We thought we would be inside but there wasn't any inside.
So we played outside at eight thousand + feet and it started to snow.
 

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I joined an online service to advertise my skill set and got a response from a west coast musician who was traveling to the Boston area to provide music for his friend’s Orthodox Jewish wedding. I was told the gig required tenor and clarinet, but was not informed that, before the reception, my first responsibility after the cocktail set was to play music for the ceremony. The leader assumed I knew every bit of Jewish wedding music and just kept launching into different tunes and keys without warning while I basically faked an accompaniment. After the ceremony, I had to play a Jewish folk song which I did not know but attempted to memorize on the spot so that I could lead all the men to the bride while playing unaccompanied clarinet and walking backwards down a hallway toward the reception ballroom. Fortunately once they got started, everyone sang so loud it was impossible to hear the clarinet. Once we reached the reception and that bit of tradition had been fulfilled, the dance floor became a stampede for 30 minutes as the band loudly played one fast Hora after another while the leader yelled the tune numbers in my ear. When I misheard him and mistakenly turned to an incorrect tune, he completely lost it and started screaming at me and throwing my music around with one hand while playing his keyboard with another. We finally took a break for something to eat, and when we returned, the leader instructed the band to play some standard tunes while he conversed with the bride and groom (apparently the old friend from school). We basically faked the last dance set and as I was packing up, the leader told me he had left his checkbook at the hotel and would mail me the check before he went back to California. A month later a check for less than I had been promised finally arrived. Needless to say I stopped subscribing to the online service!
 

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I forgot about this one.

The band was booked for a wedding, something that we didn't do many of. The bass player booked the wedding and hired a second tenor for the gig. I thought that was a bit odd, but I was okay with it because I knew and liked the guy. We played a few tunes. Lo! and behold! It's my ex-wife's wedding! The bass player worked with my wife and knew about the divorce AND the restraining order against me.

The situation was a bit difficult to handle. It was an acrimonious divorce that went to court over nothing. The upshot was that her first lawyer filed a restraining order against me (why, I'll never know). Then, she stiffed her first lawyer, thus delaying the proceedings. Her boyfriend stalked me to my day job. Six weeks after everything was finalized, here I am, on the bandstand, and up walks bridezilla WEARING THE WEDDING DRESS THAT MY SEAMSTRESS MOTHER MADE FOR HER as if we were best of friends.

I excused myself from the reception and said that I'd be back in awhile. I didn't return to the reception because by the time I found a flame thrower, it was over.
 

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I forgot about this one.

The band was booked for a wedding, something that we didn't do many of. The bass player booked the wedding and hired a second tenor for the gig. I thought that was a bit odd, but I was okay with it because I knew and liked the guy. We played a few tunes. Lo! and behold! It's my ex-wife's wedding! The bass player worked with my wife and knew about the divorce AND the restraining order against me.

The situation was a bit difficult to handle. It was an acrimonious divorce that went to court over nothing. The upshot was that her first lawyer filed a restraining order against me (why, I'll never know). Then, she stiffed her first lawyer, thus delaying the proceedings. Her boyfriend stalked me to my day job. Six weeks after everything was finalized, here I am, on the bandstand, and up walks bridezilla WEARING THE WEDDING DRESS THAT MY SEAMSTRESS MOTHER MADE FOR HER as if we were best of friends.

I excused myself from the reception and said that I'd be back in awhile. I didn't return to the reception because by the time I found a flame thrower, it was over.
You just may win with that one. The bass player does suck for not telling you though
 

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Mine was probably wind ensemble in a parking lot in southern California in the summer. No shade, few passer-by, no productive reason for doing this gig.
Mine was winter in CT. The band was to play for the passing sleigh ride. We were supposed to be set up in the start and end location - the firehouse. Well, the band got moved up the street in front of the town hall. The road was not busy that day and aside from the passing "sleigh" on wheels pulled by a horse, no one was there. A few local pedestrians did walk by, did a double take, smiled/laughed and kept walking. We played a couple songs then went inside to warm up. Repeat that for 2 hours. Temps in the low 30's. Nightmare.
 
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