Was it the rio mp3 player? https://en.m.wikipedia.org/wiki/Rio_PMP300 https://en.m.wikipedia.org/wiki/Rio_PMP300 I got this in 1999... So it might not fit you

Was it the rio mp3 player? https://en.m.wikipedia.org/wiki/Rio_PMP300 https://en.m.wikipedia.org/wiki/Rio_PMP300 I got this in 1999... So it might not fit your exact timeframe. My friend put Tupac's Changes song on there. That wasn't my first mp3 but it was the first on a pocket sized device.