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...