It chewed up cassettes and offered poor sound quality, but the Walkman was once the height of music technology. Join me in waving a fond farewell to this cherished – if flawed – gadget

Am I alone in feeling a small degree of sadness after hearing that Sony is retiring the Walkman? Like vinyl-lovers who mourned the arrival of cassettes, I finally understand what it's like to watch a piece of music technology, once regarded as the pinnacle of cool (no, really), fall from grace and, in the Walkman's case, suffer a quiet death.

I first got my hands on one when I was about nine. It was pale green and I smuggled it to the edge of the school playground with my friends, unfolding the casette sleeve to the Robin Hood: Prince of Thieves soundtrack so we could sing along to the words. My other memories are less pleasant: the damned thing chewed up lovingly made mixtapes, slowed down malevolently as the batteries died, not forgetting the rubbish sound quality it offered. Finally, I threw the last one I owned at the pavement in a fit of tech-rage – aged 14, I think, this time with only slightly improved taste in music – and turned my affections to the latest revolutionary gadget (which turned out to be just as rubbish), the MiniDisc player.

I wish I'd kept the mixtapes I'd made back then, but they were thrown out along with my Now That's What I Call Music ... compilations. Then again, I seem to remember a personal selection that featured Shampoo, Salt N Pepa and 4 Non Blondes. So please join me in waving goodbye to this flawed piece of technology, and let me know which songs best capture your Walkman years.