Nostalgic, I did this when I got my first ever iPod. It was never any measure of fun, but I felt like I was striding between the eras again. Behold, the age of digital.
I gave up buying CDs some years back, now Apple hold my soul in escrow in exchange for lossless, spatial audio* in Dolby Z or somesuch which streams nicely to my Sonos (actually from my phone, via Apple Play, I don't get on with the voice thing after The Christian Rock Experience). Not as awesome as pressing the 'metal' button on a cassette deck, but it'll do.
*while it has some capacity as a gimmick, I confess it's pretty awesome if you dance around the living room in AirPods. Clothes are optional but check for errant dinner guests before embarking on this course of sonic self-entertainment.