To be fair here, I don't think the technology is "better", but when you complicate something there tends to be more things that can possibly go wrong with it. Also, my original iPhone still works, and is like 5 years old. I don't forsee it breaking in the 10 years it's going to sit in my iPhone 4's case, similar to your walkman.
Anyway, wanted to come shit in your cheerios with that.
I did have a walkman. I even had the Sony boombox that was huge and yellow and you could pull out the middle, separate from the speakers (basically turned into a walkman). Yeah, I was spoiled.
Bookmarks