I was DJing in the late 80's which was still in the sweet spot for making mixed tapes. I was always happy to make a tape for anyone who asked at a gig, great way for this music nerd to meet girls. I was basically John Cusack in High Fidelity without any game. Even with turntables and mixer, it was a decent amount of work to make a good tape with clean mixes and decent flow for the length of a tape side. Still have some of my vinyl, but the tapes are sadly long gone.
Early 90s I was going to school in Ontario and I would drive back and forth every fall/spring in my pickup with only a tape deck. In 92 my brother-in-law's brother who I didn't really know needed a ride to ON so I figured why not, nice to have company. He wasn't digging my rotation of Metallica, RHCP, ACDC and asked if he could grab some tapes at the next gas stop. He came back with Wilson Phillips, not even kidding. I was then subjected to hours of that effing Hold On song, because I was apparently way to effing nice. Dropped him off in Kapuskasing and he neglected to retrieve his tape. As I pulled out of town, the tape was heaved into the ditch next to highway 11. To this day I can't stand that song.
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