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My first MP3 player was a parallel port one in the early 2000s. Think I could just fit one low quality album on it.
aggi-
Ah yes, Diamond Rio PMP300. Kept that one when I did my clearout. I got it the day it was released as I was living in SF at the time and whoever I ordered it from shipped it a day early.
Used to use it for cycling by sticking a load of music on it, downsampled to mono 32kbps mp3 to cram in as much as possible. (Who needs quality with crap headphones and wind noise.)
Greenbank
The last actual parallel port stuff I had, other than a printer, was a Zip 100 drive back in the last 90's.