My old fella used to work in Singapore, 1983 onwards, me and my sister got some of the first Walkmans that anyone in our town had seen, the orange sponge headphones - absolutely magical back then, walking around with music playing that no one else could hear! A backing track to real life.
Bought a flash Sony Discman that had the delay/skip function when I first moved to NYC in 99, used to ram it into my back pocket and wander aimlessly around the East Village, even then it seemed pretty amazing. Pace of development since then has been astounding, wireless noise-cancelling earbuds playing any tune you want.