Portable CD players were a frickin nightmare in hindsight. Earlier decades had it better with tape players.
These CD players were 'amazing technology' advanced from tapes, but the second they were shaken, the music would stop. So even if you're just sitting on the bus with this clunky ass machine on your lap, or not walking smoothly enough, the music will jitter and even come to a complete stop for a while.
Then they invented 'anti-shock' or whatever, and they would price their product based on how many seconds of shock absorption they could handle. I think mine topped out at 5 seconds.
The headphones themselves absolutely fucked my ears - I have tinnitus to this day because I was an irresponsible brat, but also there just was no limit to how loud those things could get. So we would like... compete to be the loudest person on the bus for some reason??
In the same way people just play tiktok on their phone speakers now, we'd literally have headphones readily available, but take them off, wrap them over our ears or round our neck and just blast the music so damn loud everybody could get annoyed by it, while we thought we were being super cool due to our cool music taste.
But then you'd apply that volume even when it was directly in your ears, so I'm sitting listening to Cradle of Filth with zero consideration of health and safety from either party. No noise cancelling existed, so you HAD to play that loud a lot of the time just to hear your music with any clarity over whatever public noise was going on around you.
Also, batteries weren't rechargeable (they existed but were not built into anything really except phones). So you're just constantly switching out 2 big ass AA batteries every few days.
And you had to wear big baggy trousers in order to accommodate the sheer size of a CD player in your big fat pockets. Skinny jeans just couldn't hack it.
At one point the crappy hinged lid broke off mine and I managed to keep it running without the top off so I'm just balancing this little broken player with its scratched CD on my knee on the school bus delicately trying to get my morning music, interrupted by all the damage of moving parts.
God.
And the thing is, the trade off was meant to be higher quality music. And while this is true, in hindsight that's no longer even a good thing. The Loudness Wars (an actual thing) making every production as loud as humanly possible isn't even a thing anymore. Streaming platforms actively suppress this loudness even if you upload your new album at the volume of a nuclear detonation.
And with that pure, digital quality came the sterility of productions. Everything sounded artificial. There is a reason people still to this day love Vinyl. The imperfections bring a human warmth to music that may no express every microscopic soundwave in the original performance, but our human brains fill that in with our own personal expression of beauty.
So it really was just an utter waste of technology and we should have just skipped straight to the iPod from tapes.