I had the gameboy, commodore 64, spectrum 128k, 512k etc... I guess music players is where I geeked out when I was young.
I got the Sony WM-B603 walkman in about 1990 when I was 6, this was the bee's knee's it could automatically flip your tape over and it was about half the size and weight of a lot of the other kids walkmans at school, plus i had a bass button! I had a set of audio technica over ear headphones which were also the best sounding thing ever. I think there are still in the garage somewhere.
Then I upgraded to a minidisc player as I also had a minidisc player in my stereo, i think I was about 15 as the cassette player was just not updated for many years.
This was not as a good of a model, it was a Sharp MD-SR60 but it allowed recording if I went to a friends house to steal their prodigy albums.
Then I got my firsr proper PC and I had Winmx and audio satilite and could get music online (56k dial up). So I was given an mp3 player.
I had two I remember, the best being the panasonic SV SD75
This was pretty revolutionary back then, it was small and could fit on your arm or hang from your neck. You could store a massive 15 songs on the 64mb SD card which took forever to upload onto.