I still remember quite a few people carrying around a "Discman" in the later part of the 1990s. Their size eventually shrunk down to about the size of a CD jewel case. With added shock-protection, those devices were even semi-usable during sports or while biking. I still remember illegal mix-CDs becoming highly popular in Western Europe. It's true that those things never really fit into your pocket, but I have the same problem with some of the almost tablet-sized smartphones of today, yet people still are getting around with them...

I guess the reason for MiniDisc never really beating the mix-tapes back in the 1990s, is because both players and recorders remained fairly expensive, compared to portable cassette players and later iterations of portable CD players. It also didn't help that it took Sony many years to license the technology to other parties. Before mass-digital flash storage in SD and USB disks became the norm, MiniDisc was by far the most portable, near-CD quality storage medium available.
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