>>With music I can cross the entire city on foot and more.
I'll play Devil's Advocate here and say that the Walkman marked the beginning of the end for people having spatial awareness and social skills in public places.
You've only got to look at all the people meandering through our city streets today; ears plugged with headphones, faces glued to screens –often walking along with other people but yet completely detached from them, barely conscious of the world around them– to see what the Walkman's legacy is.
Personally I prefer to listen to my music on headphones when I'm alone and at a fixed location, rather than bimbling around, getting in other people's way and with my safety compromised by having my senses plugged up. I've actually seen cyclists riding in traffic with cycling helmets on [y'know, for the safety!] but also wearing headphones. Makes me cringe every time I pass one, knowing they've purposely cutting out the sounds of the traffic around them.