I suppose that this has less relevance, what with all the streaming and whatnot that the kids do nowadays, but I'm pretty sure that it was the Serendipity Singers, Crooked Little Man for me. Ok, I'm pretty sure my mom bought it for me, but what what single or album started this whole thing for you?
I think it was a Weird Al tape.
It's been so long I don't remember exactly.
The first tape I ever had was a hand me down from my parents, it was a Billy Joel album. "It's Still Rock and Roll to Me" was my favorite song on that album.
When CDs became popular I bought Nirvana, Black Sabbath, Nine Inch Nails, Tool, Rob Zombie, and some others. My parents wouldn't let me own a Marylin Manson CD but I would have got one if they would have let me. At the time they required IDs or parental approval for explicit lyrics CDs--there was a whole "morality" thing at the time with people over-reacting and thinking certain artists were going to create an army of Satanists. Stupid really.
Eventually I was buying stuff just because other kids were, some of my biggest purchase regrets were Chumba Wumba, Smash Mouth and Eiffel 65. Popular at the time, in retrospect pretty awful.
In high school I was buying up some old blues albums since I had a phase there. Muddy Waters and Robert Johnson were my favorites.
I don't remember in which order I purchased my CD collection--it's all gone now. Someone stole it when I was in college. With digital music becoming popular I didn't bother replacing it all. Now I just use Spotify.