Being an old guy, I caught the tail-end of 8-track era, which was the portable music solution of the day. Well, it was the mobile, as in car installation, solution. I don't remember seeing any portable 8-track players, the kind you could carry around with you, but they probably existed. The Sony Walkman's were cassette players but didn't come along until later. I think boomboxes didn't show up until the 1980s though, and they were cassette players/radios. I had just started collecting a few 8-track albums when cassettes began to supersede them, so I had to switch over. For a brief time in the 1970s, if you went into a store, even gas stations and convenience stores, you would see a rack of 8-track tapes and another rack of cassette tapes. I still remember all the glistening streamers of discarded 8-track and cassette tape blowing in the wind next to every road because those tapes would self-destruct a lot and get tossed out of car windows. (Roadside littering was really terrible in those days, at least in my part of the world.) Good ol' magnetic tape medium stretched and warped with every play of a tune, then soon enough the player would eat the darn tape! Extracting the cartridge from the player more often than not unwound the tape and hence the reason so many were discarded along the roadsides everywhere.
Then came CDs and finally digital. But I learned my lesson way back in the 1970s, and that was to not throw away hard to get money on tunes that will self-destruct. An even if they don't self-destruct, I got tired of hearing the same darn few songs over and over again. I guess it would be different if I could own a million tunes, but that will never happen. Even a few thousand get old rather quickly. Now a days I just listen to the radio or subscribe to a music service (currently use SiriusXM). I think I only own maybe a hundred songs on digital, and I long since got tired of hearing those, so I rarely play them anymore.
I still think the best era was when we played our vinyl records. Mom had her swing band music from the 1940s on old 78s, we had our 45s and LPs. Portable, however, was not a word we associated with music back then unless you listened to a car radio blaring out monophonic tunes on a squelchy AM station a hundred miles away.
