Sorry, but Walkmans and Discmans were considered cool... At the time.

Personally I like simple designs. I always remind people who make posters that whoever looks at them will only do so for a matter of seconds. If you want extensive detail, put it in smaller print. Put the main hook in large letters and a brief description.

But they became uncool when the iPod and mp3 players came out. Nobody felt sentimental about VHS artifacts either, and now it's a genz aesthetic or something. These things cycle, like I'm sure some old folks miss the radio hiss and listening to football matches with just audio.