I managed to convince my mother to buy me a Sanyo walkman back in 1985. Still keep the original box, demonstration tape and bill. Something like $75 -25 years ago!!! Today you can buy a 2 gb mp3 player for like $10.
I would not go anywhere without it. I would carry some spare tapes to change the music. It was an auto-reverse with graphic equalizer- top of the range, but I would have not mind to have one with radio too. When the batteries run low and were unable to move the motor, if you had radio you still have more minutes of entertainment....
I used it to jog. Attached to the shorts with the belt clip was useless - at the third stride it would jump off. So I had to jog with it on my hand. I put it inside a plastic bag to avoid the sweat getting into the internals.
One way or the other, it sometimes got the occasional blow or fall, so the door hinges broke and I fixes it with a pin and loctite. Also the jack solder would break every now and then and I had to open it and re-solder. Always carried a pen to rewind tapes and save battery life.
I even built a rectifier to use the bicycle generator to power up the walkman so I could ride the bicycle and listen to music. When you slowed down, so did the music.... :-)
Five years later my wife -then girlfriend- bought me an Aiwa walkman. This time with digital radio. I also took it with me everywhere, but I was 20 or so and didn't use it for jogging. Very soon I discovered the CD and got me a portable CD player. Talk about high battery consumption. 4xAA cells would last just a couple of CD's. That was the reason to switch to reachargeable batteries.
It was impossible to jog with it, the slightest shake would stop the music. A couple years later I found a good price for a CD player with 40sec anti-shake buffer. Nah, didn't work either, you started to jog and the music didn't stop, but 40sec would help just for the occasional shake, not a continuous shaking.
Then I found a CD player with remote control for $10. I was already paying attention to mp3 players, it was 2002 and a 32mb mp3 player costed like $100. There wasn't even space for a full CD! Got me the CD player, it was practical as I could carry the CD player in the backpack and mute and stop the playing with the remote.
My first mp3 player costed like $120 and had 256mb space, something like 4 CD's. I have had three or four since then, usually the price remained similar but the capacity was four-fold. Now I use the phone to play music, but only listen to it while commuting on the train or the like....
I have managed to buy three or four walkmans out of ebay, like the first one I had, and keep them only for nostalgic reasons. When I have to explain my kids what is a compact cassette or a VHS tape I feel old....