The oldest thing I bought and still use is a stereo system I bought from Future Shop in 1994 using my cousin's employee discount. The CD and tape players stopped working a long time ago, but I still use the radio every day as my second alarm clock.
The oldest thing I own AFAIK is a PolyTel compilation tape called Rap Traxx 2 from 1989:
As you can see I put scotch tape over the tabs so I could record over it. I have no idea what's on there now.
P.S. this track list is full of bangers!
"So you're a philosopher?"