My friend has an old cassette boom box hooked up in his garage to nice speakers and plays The Cure and old Industrial music from cassette tapes and it honestly feels like the music was written for that specific medium.
The first time I heard Nine Inch Nails was Closer, from The Downward Spiral. It was being played on one of those tiny set of speakers plugged into the headphone output of a walkman... and it was glorious :)