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Small Town… Small Bar…

No written contract is needed for a value of less than $500 dollars. I’m guessing the venue of 50 or less seats isn’t paying more than that. If you have a valid offer, an acceptance and the $500 in consideration then you have an enforceable contract. The argument of the band not bringing in enough people is immaterial to the contract and they wouldn’t reasonably be able to argue any frustration of purpose or impracticability of the agreement.
This is not true. A verbal contract for services is enforceable regardless of the amount.
 
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hypothetically, the band leader or the bass player would suggest to the bar owner that they brought most of the hypothetical crowd, and that not paying the band would not only - hypothetically - guarantee the band would not play there again, but that none of the band's hypothetical followers would be going to the bar again after they heard the band was stiffed. hypothetically.
 
Maybe. But I've done dozens of these for bands and never had a problem beyond negotiating minor terms. It doesn't have to be long, one-sided, or complex. It protects the venue and the band, so if the venue is dealing in good faith, they won't have a problem with it. It also lets the booker know they're dealing with pros and not a fly-by-night garage band.

I don't know what their thinking is. Maybe they don't want to bother with 1099s since these places are cash at the end of the night around here. I won't speculate about their other bookkeeping practices.
 
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When the final Tragically Hip concert was aired live, our band was booked at a local bar. We figured no one would come out - everyone would be home watching the Hip. We called the bar and asked if he still wanted us to come, and he said yes, he expected a decent turnout.
We went, set up and started playing at the agrred time, but we were just playing to the bar staff. By the end of the set there were only a couple of stragglers at the bar. We told the owner that we would be happy to take half payment and just go home, but he insisted we finish the evening. We did the second set to about 6 people. And at the end of that set we made the same offer to the owner, which he declined. So we did our final set.
When it came time to collect our earnings, the owner said that he couldn’t pay us since the bar didn’t make any money that evening. We got zip.

We spread the word to the musical community, and to the Mayor of the town whom we had come to know in the previous years. Consequently the owner couldn’t find a band willing to play there, and regular customers of the establishment stopped patronizing the place. Within a year he was out of business.

Hah! Fixed that.
 
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Had I been the hypothetical band leader I would have cashed that check using my banks scanning phone app so fast the hypothetical bar owners head would twist.

I've been through this scenario a number of non hypothetical times and I get really surly at the suggestion of breach of contract on the part of the venue.
Having run a different type of small business for a decade I have the speech memorized:
"We will take you to small claims court and we will win. We will sue you for treble (old English common law term meaning triple) damages and we will win. We will ask the judge or magistrate to apply court costs to your business. And finally, each band member will tack on their loss of dayjob income for the day in court.
'so you can pay us $500 tonight, or several thousand when the case hits civil court. What say you?".
Speaking from experience-You’d win a judgement for the agreed amount, and not be reimbursed for your time in court.
 
Last time that happened, we not-so-hypothetically refused to leave until we were paid in full.

When a check was offered, I told the owner that their bad-faith behavior put them on credit hold; They were welcome to pay by check, but we were there all night until they cashed it.

No question they woul've stop-paymented that check before we tried to deposit it; It's not a criminal matter for a business to write bad paper.