Its sad these days that no one on here really remembers the days of waiting all day to have your favorite song played on the radio with your fingers ready to jump on the play/record buttons. You always missed the first 15 seconds of the song or had the DJ's dialog before the song started (if you caught it on a top 5 at 9 or whatever) I had a walkman since 1992 and I still even have it. Great post. Walkman>Discman
I remember catching songs on the radio in elementary-middle school, but I only had a few tapes because the flawed intro just messed with my music OCD (whole songs. whole albums. straight through. *twitch*) University radio wasn't as bad about DJs talking over the music, but you could never tell what you were going to hear.
We made some mix cassettes from vinyl and (much later) I always had a few CDs transferred to cassette in case my CD player died. This approach was probably shaped by the southwestern climate, which would melt/warp tapes in the car while running errands. A VCR was actually my 90s magnetic recording device of choice: videos, 120 minutes, PBS concerts, sci-fi shows, "count" noted on the label for fast-forwarding.
The Walkman's portability and ubiquity was so important, though. It was really the first fully-functional, semi-ergonomic portable device. iPhones didn't look like early cell phones. They looked like/functioned as iPods, and I think that's an insight that was built on Walkman's legacy as well as Apple's success.