Originally Posted by Athens80

Yes, someone sometime took a picture of someone else riding with a pair of foam covered headphones lightly resting over their ears. And then someone edited the image so that we see it on the internet today in black and white and thus it looks old.

Not every picture in the newspaper depicts an everyday event, anyway. Some pictures are taken of usual events.

That picture was not taken 40+ years ago, assuming that 40+ means more than 40. And riding with a Walkman wasn't a common sight even 40 years ago.

It took a while for sales to take off for any use, at least outside of Japan. Perhaps the cost, in today's terms, at USD 500+, played into the initial adoption rate. After a while, like the iPod, it became popular anyway. But never popular for people riding bikes, anywhere I saw.