Ones I bought legally (or semi-legally, as with bootlegs):
1. Super Mario 64
I found a few copies of these at a Walmart. Appearantly they came as freebies for Walmart's subscription to the magazine. The cashier couldn't find a price on them so they gave it to me for free, and this was the first music CD I ever owned. I still have it, too.
2. Banjo-Kazooie
This was again a freebie offered with a renewed subscription to Nintendo Power but this time it was with my own personal subscription. A happy go lucky soundtrack for sure, but better than some give it credit for.
3. Klonoa: Door to Phantomile
Scored an original copy of this from eBay. One of my all time favorite games and great music to go with it.
4. Parappa the Rapper
This along with Klonoa was one of my motivations for getting a PSOne. Eventually I got an original Parappa OST from eBay. It was amazing to me at that time because it was one of the few games then that made great use of music and storytelling.
5. Sonic Adventure
Ironic story about this: I had been searching for this OST forever when a complete copy appeared on eBay. I fought a bidding war and won it for $50. The item came and it turned out being an EverAnime bootleg. I contacted the seller and we agreed to a partial refund for two reasons: 1) I wanted to keep it despite this and 2) because it was a bootleg and having knowledge of it being rare period, he wanted to compensate some portion of it. Not long after, someone listed a legitimate, still-sealed copy of the same OST which sold for a mere $20. Tsk, tsk. Still a favorite though, and much better than the second.
6. Sonic Adventure 2: Official Soundtrack
This is the legit US soundtrack which leaves a large chunk of the originals omitted, but good for what it was. I got it at a GameStop.
7. Sonic Heroes
The official version. Not one of my favorites, but the instrumental tracks are bearable.
8. Fantastic Night Dreams Cotton
Another eBay purchase but I recently sold it to a local record store for $10 in credit. It was never a favorite and I had a hard time getting rid of it so that's where it ended up.
9. Vectorman
This is part of the Sega Tunes series. Suits actual gameplay better, as this is pretty standard techno fare by itself.
The rest is stuff not worth mentioning since it's mostly bootlegged Sonic soundtracks (had no idea when I bought them) and some legitimate pachinko music compilation. I'll update you when I find anything else I have worth mentioning.

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