I've always loved boomboxes, especially when I was a teen. I had a difficult puberty and music has always been (and will be) a haven of calm and enjoyment.
I have already had a few boomboxes, starting with a couple very tatty, reaching an excellent one, passing through several intermediate.
I think I have a good "ear smell": seeing the look of a specific model and its specifications I can quickly have a pretty good idea of its quality. This smell hasn’t failed me, I have hit pretty well most of the times.

Actually I always have been more interested in Walkmans than in boomboxes, for one simple reason: I care so much about sound quality. In my case, to have a listening room with excellent acoustics, a high-end stereo and total isolation is simply impossible. Instead, enjoy a similar sensation thanks to high-end headphones, it is possible (and I think today I already have a set-up that meets enough my needs in music terms).

It is also true that intimacy and isolation that provides a Walkman with good headphones is something that in my opinion is unbeatable.

For these situations where you just want some background music while doing some daily tasks at home, but not looking for extreme quality, a boombox is perfect. Still, I’d no take any sardine can.
Right now I have no boombox at home. I have my HIFI ONKYO stereo in the living room, and my little Cambridge Soundworks speakers connected to my sound card X-Fi in my PC which both satisfies me needs enough.

But I recently acquired a very special radio cassette: the extraordinary AIWA Strasser SR8, which for me is the best boombox ever made, for many reasons.

The AIWA Strasser CSD-SR8. Photo: Unkown.

I have had a Japanese friend at ’92 which had one of this at his room, and I always was very impressed about it’s quality. I was at the university, living in a student residence, and I could hear and play a bit with almost all student’s boomboxes then, of many of my colleagues (about 100 in total) and, believe me, this SR8 beated them all by a BIG margin, even with bigger boomboxes in size (I remember there were some big Panasonic also).

I would like to explain why do I think that this is the very best boombox ever made, and which are (IMHO) the weaknesses of many other models that are very popular. First of all:  because of it’s high sound quality, closer to a small HIFI than to a boombox.

Definitely, for me the most important characteristic is the sound quality. If I had to put on a scale of 0-10 different sound sources, would underscore the natural sound:

The Chicago symphony orchestra. Photo: unknown

And in the last position, the sardine can:

So, this is how I score their audio quality:

(all models are in approximate scale)

Again: this is my particular view on all these devices. If I'm wrong at some point, I'll be happy to hear comments.