Clementine is great. If you look in the library on the left you can right click "Smart playlists" and select "New smart playlist...". Then you can create a play

Clementine is great. If you look in the library on the left you can right click "Smart playlists" and select "New smart playlist...". Then you can create a playlist of all your music (or with additional filters) that is either randomized every time you open it or built dynamically as you listen.