So, from experience, I don’t think it likes it if you play a song too close to itself. I had a short Playlist once with two or three songs bookended with Photograph, and it dropped the second Photograph. So I’m hesitant to do the same song over and over. Maybe a song that has a whole bunch of different versions might work!
Could you do a solid prank for this random internet stranger and queue up the following:
8 x one favorite slightly annoying song (‘moves like jagger’, or ‘we built this city’ would be my suggestion)
1 x Photograph (pause for the unison sigh of relief from the patrons)
1+ x the same slightly annoying song played in a row already.
I’ll bring popcorn.
So, from experience, I don’t think it likes it if you play a song too close to itself. I had a short Playlist once with two or three songs bookended with Photograph, and it dropped the second Photograph. So I’m hesitant to do the same song over and over. Maybe a song that has a whole bunch of different versions might work!
You could at least credit John Mulaney if you are going to steal his jokes.