load a digital audio player with the content of a playlist randomly generated from a folder

[sentinel166]

Hi
Everything's is the title.
Maybe it's simple, maybe it's not, I have no idea honestly.
I want my playlist to be randomly generated, then to somehow synchronize my audio player with it, meaning copying and pasting the files in it (NOT an Apple device or bothersome).
I guess there is a plugin to do just that as I am not the first to think of it, but I don't know what to look for exactly.

Thanks !

ps: if there is a simple non vlc way to do this, I'm ok with it... I have windows btw.