On my phone I have a micro SD card with thousands of Mp3s on it yet I catch both Google Play Music and VLC player playing the same progression of music over and over when I have the random button set to on... I thought this was because it was a tactic to get me to upgrade the music players I was using, but it also happens lately on all kinds of devices I use.
YouTube, Spotify, and SoundCloud provide revolutionary services yet it seems like a lot of the time I am listening to pre-arranged and designated music playlists rather than a truly honest music stream.
In the days of the 5 disk CD changer, people truly knew what random meant. no tune was played twice until all of the tunes were played...
1. I want it to play in a truly random fashion, with replacement (same song twice in a row is possible).
2. I want it to play in a truly random fashion, without replacement (each song is removed from the list once played).
3. I want it to "seem" random (don't play too many songs by the same artist in a row).
4. I want it to be random, but predictable (same "random" ordering if I start the playlist again).
5. I want it to play my favourite songs more often than my lower-rated songs.
6. I want it to play my less-commonly played songs more often than the stuff I listen to all the time.
So: what exactly do you want when you say random?