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The "earliest" samples of "acrobatics" that I have seen at weddings were bottle dancers, which seemed to be popular among Hassidim, and I guess originated from Russian custom.

The Talmud mentions in several places that it is a special mitzvah to gladden the bride and groom at the wedding. I recall reading a story mentioned in Avot Derav Natan that one rav would interrupt his studying when he saw a bride and groom pass by him on the street, and he would dance before them.

Gladdening the bride and groom can be done in various ways, I assume. But, from what I could find, in Tanac"h it seems to mention music and joyous sounds, and dancing. It doesn't mention acrobatics or the use of "shtick", like wearing funny hats, "leis" or costumes.

Is there any older mention of physical "stunts" or similar physical feats/skills performed at Jewish weddings such as a mentioning in the Talmud or similar? When and why was this introduced as a means of gladdening the Chattan and Lallah (bride and groom)?

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    Shmuel 2: 6, 17: "וְהָיָה אֲרוֹן יְהֹוָה בָּא עִיר דָּוִד וּמִיכַל בַּת-שָׁאוּל נִשְׁקְפָה בְּעַד הַחַלּוֹן וַתֵּרֶא אֶת-הַמֶּלֶךְ דָּוִד מְפַזֵּז וּמְכַרְכֵּר לִפְנֵי ה' וכו':" – Al Berko Jul 24 at 15:11
  • Well by the simchas bais hashoeva they had juggling and one finger pushups and so on,and it was considered the most joyous event ,so anything ppl do to mimic that can be called joyous ,hence why people perform such acts by weddings – sam Jul 24 at 15:30
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    Maybe we should institute a fiddler-on-the-roof tag – chortkov2 Jul 24 at 15:44
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    Not exactly pro-level acrobatics (like in the BHM, cf. Sukkah 53a) but an example of various kinds of wedding entertainment is in Ket. 17a. – Oliver Jul 24 at 15:46
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    @chortkov2 Not needed. I've seen it live several times. I can't say for sure, but, I think a few of them were using full bottles of expensive single malts, too. – DanF Jul 24 at 15:58
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I don't know if it's the earliest but Kesubos 17a provides three examples of shtik.

אמרו עליו על רבי יהודה בר אילעאי שהיה נוטל בד של הדס ומרקד לפני הכלה ואומר כלה נאה וחסודה רב שמואל בר רב יצחק מרקד אתלת

With regard to the mitzva of bringing joy to the bride and groom, the Gemara relates: The Sages said about Rabbi Yehuda bar Elai that he would take a myrtle branch and dance before the bride, and say: A fair and attractive bride. Rav Shmuel bar Rav Yitzḥak would base his dance on three myrtle branches that he would juggle.

רב אחא מרכיב לה אכתפיה ומרקד

Rav Aḥa would place the bride on his shoulders and dance.

A more extreme example is Tosafos in Sukkah 45a s.v. מיד describe fighting on horseback at weddings.

לאותן בחורים שרוכבים בסוסים לקראת חתן ונלחמים זה עם זה ...שכך נהגו מחמת שמחת חתן

Those young men who would ride on horses to entertain a groom and would fight with each other...this is what they were accustomed to do, to provide joy to a groom

Although I have to look into it, but this Tur might shed light on Tosafos that they're referring to escorting the groom to the wedding. But same idea. I vaguely translated לקראת as entertain, but a better translation, especially according to this Tur, is greet.

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    Yes, that Tur is referring to this then prevalent form of entertainment. His contemporary Mordechai b. Hillel(AKA ‘The Mordechai) too referred to it (Sukkah §743). – Oliver Jul 24 at 18:54

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