I got off to a rough start.
I had, used and loved a clock radio for years before this, but the first music I truly owned came from a playground friend, who bought me a tape single of Third Eye Blind's "Semi-Charmed Life", with "Tattoo of the Sun" as a b-side. (Like Dan, I'm a baby.) After about a week of of solid playback on both our living room stereo and my dad's ancient JVC portable, I got tape fever.
I bought a few more from the dollar bin at a mall chain that doesn't exist anymore, choosing based on some ridiculous cover art criterion (I think it was "it should look like that House of Pain tape that I'm not allowed to buy") which netted me two completely unmemorable albums and one that I recall being called something like Mean Streak, and as having three hair band-looking ladies on the jacket. There is absolutely no evidence on Amazon that this album ever existed. So, I stopped buying music for about a year after that, because it seemed really hard.
The next Christmas brought a Sony CD boom box into my life, along with Chumbawamba's Tubthumper and something by Smashmouth. A 12y/o family friend with cred beyond his years sent me a Busta Rhymes' Extinction Level Event: The Final World Front that year, which I foolishly shelved.
Although to be fair to my reputation, the first truly premeditated music purchase I made after that Christmas was much cooler: Dada's Dizz Knee Land. Thanks for the tip, Aunt Diane.
For Gizmodo's week-long Listening Test (a tribute to all things audio), each writer will be sharing his/her first album. In other words, there will be many more to come.