The current popularity for all things jester-related can possibly be traced back to 2021, when the concept of ‘Jester’s privilege', as explained by a Wikipedia article, became a concept that many attached themselves to. It describes how a court jester has the right to mock whoever they please without facing any punishment for their teasing.
Around the same time, the first mentions of ‘jestermaxxing’ emerged, although primarily in a negative context. It was used by men bemoaning how they felt that they would only get attention in social situations if they played the fool.
The combination of these origin stories gives a succinct explanation of why the jester is the perfect meme character for the point we find ourselves at with internet culture. People are sick of being afraid to express themselves without fear of criticism, cancellation, or being bean souped (the way that some behave online as if they cannot grasp a concept unless it directly relates to them).
At the same time, many of us feel more like a performer than ever in our everyday lives, with the cult of the influencer leading many of those who are chronically online enough to believe that everything requires a song and dance.
Calculatedly goofy, the jester is an even more performative rendition of the sh*tposter who came before him. In a way, he's sick of it all, but he is going to put on a show anyway.
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