Beit Midrash
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- Bemare Habazak - Rabbis Questions
Answer: Since this case is no longer practical, we can discuss more freely both principles, and possible arguments relating to this specific case.

Bemare Habazak - Rabbis Questions (627)
Rabbi Daniel Mann
327 - Giving an Envelope on Shabbat to Use for Donations
328 - Paying for Unscheduled Entertainment
329 - Men Going to the Mikveh before Rosh Hashana
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There are subjective factors that help determine whether a job was called for. For one, the Rama (Choshen Mishpat 375:4) rules that if the field that was planted was owned by a man who usually does the work himself, the outside help is considered largely uncalled for. Even though most people would appreciate the work, the main benefit is saving the owner from hiring another worker, so when he does his own work, the owner only has to pay for the benefit of not having to toil. In the other direction, according to the Shulchan Aruch (CM 375:3) if the owner "built on" the work that was done, he cannot subsequently claim that he did not gain from it. The Shach (ad loc. 3) cites dissenters. One has to weigh the circumstances in each case.
Let us analyze your case. One could claim that the work was done with the beneficiaries’ knowledge, and therefore they should be responsible. However, this is wrong because their silent acquiescence was based on a misunderstanding, and agreement b’ta’ut does not obligate. The lack of protest could have some significance. There is an opinion that even when a recipient did benefit, he is exempt if he warned that he refuses to pay (see discussion in Pitchei Choshen, Sechirut 8:(64)), and here they at least did not warn.
Should we characterize the performance as fitting, since people enjoyed it, and enjoyment is valued at weddings? I have attended many weddings and am hard-pressed to remember such a performance. Most people pay good money for a band, and participants often do creative shtik, but professional shtik is uncommon in the circles I know, even at weddings at which expense is not a factor. Therefore, it would be difficult for the entertainer to prove that he deserves more than a return of expenses, which are presumably small.
Furthermore, benefit refers to net benefit (e.g., regarding the field, the vegetation planted must be preferable to alternatives). Even if many people enjoyed, others could have been appalled by such a childish performance at a wedding. Also, the time taken on it may have taken away from "valuable" eating, dancing, interacting, etc. time. Therefore, it is again hard to ascertain that there was benefit.
In all, it is unlikely that the families could be forced to pay any significant amount of money for this uninvited performance. Although the propriety of the entertainer’s actions was very questionable, paying him a not insulting amount might have been a proper act of chessed and/or avoiding machloket. (Others might argue that such a person must not be encouraged to do such things.)

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