Shuffle Music videos in folder Hierarchy

I have my music videos in a layout Plex/Jellyfin prefer and I’ve noticed that I am unable to shuffle them. If I just dump them all into a folder it works but to get the most out of my metadata the layout below is preferred.


Music Videos/
|- Artist 1/
|    |-folder.png
|    |-Song 1/
|       |-Song 1.mkv 
|       |-Song 1.nfo
|    |-Song 2/
|       |-Song 2.mkv
|       |-Song 2.nfo
|- Artist 2/
|    |-folder.png
|    |-Song 1/
|       |-Song 1.mkv 
|       |-Song 1.nfo
|    |-Song 2/
|       |-Song 2.mkv
|       |-Song 2.nfo