I started using Winamp in the 90s when I first started ripping CDs and listening to all of my music in one playlist that has been randomized and played on shuffle.... once I met my wife, we combined our music and started borrowing all of our friends' CDs and ripping them until we had about 40gb's worth by 2005. I also added thousands of >10sec clips and quotes from TV & movies as well as hundreds of hours of spoken word from people like Chomsky and Jello Biafra... so when all those tracks are mixed up like that, it started to have its own personality.
Our nickname for our computer was "The Wow Machine" so we started calling winamp on randomized shuffle, "Wow Machine Radio."
We tried out other players, but all acted more like the way OP described his original experience... they all seemed to repeat the same songs within a pretty short interval.
Not winamp.... once the playlist was randomized by holding down cntl-shift-r for 10 or more seconds and the result played on random... we NEVER knew what would play next.
HOWEVER, As crazy as it sounds, my wife and I have commented to each other on many occasions over the yearsabout how it seemed like Wow Machine Radio seemed to be playing selections as though it had a theme in mind. I won’t go as far as saying it is actually intelligent, but it has made me ponder how artificial intelligence would manifest itself. I’ve stayed up waaay too late many times simply waiting to see what the next track it would “randomly” choose, marvelling at the moments when the next choice seemed to ‘fit’ right into place.
As for criticism.... if and when winamp crashed, all of the 'recently played' since the last load was LOST. I've always wished there was a 'subtracting feature' to the playlist... so, even if randomized and shuffled, once played, the track would just drop off the list and you could be sure you wouldn't hear it again.... if not that, then some way to easily remove just the tracks that had been played recently.
Anyway... I just wanted to weigh in on this old thread because the Random/shuffle features on Winamp was always THE thing that kept me using it. The worst player I've found is iTunes.... somehow, it has a way of playing from the SAME library, but making my own music suck. Winamp, for some reason, has always been entertaining in its' shuffle for me.
We just resurrected Wow Machine Radio when we found out there was a rollback in the build.... we'd stopped using Winamp for the last five years when AOL bloated it up into an unstable mess.