back when I used Winamp as my daily player, I was getting annoyed that its "shuffle" kept playing the same songs. and it would play the same songs in a row. so I would hear the songs C,A,F play. then the next day again the sequence would be C,A,F. over time, I would start hearing the melody of the next song before it even started playing.

when I finally noticed this and realized that could only mean it's not actually random, I researched it, and found out that once you hit shuffle/random on Winamp, it shuffled the songs once and kept the sequence forever.

and then as it turned out, Winamp actually had a setting to select a truly random song each time. all I needed to cure my madness was a checkbox!