The BBC had a 13-year old swap his iPod for a Sony Walkman. It's a pretty fun read as the kid compares the two portable music devices.
I loved my Walkman. I took it everywhere and spent a great deal of time making perfect mix tapes. Here I am gushing about my good ol' Walkman days back in 2004 and here I am doing it again in 2005.
Once you adapt to the iPod, there really is no going back. The shuffle, the sound quality, the storage capacity, the size... it's simply not a fair comparison. But back in the day, when we didn't know any better, Walkmans rocked.