I was a Winamp user too
The first sone I heard by Namie was a walk in the park on an old Jpop site, but I didn't get into her until a good friend of mine sent me her stuff. Namie is her favorite singer. I believe the first release while I was a fan was the single Girl Talk/the SPEED STAR. I distinctly remember coming home from school and watching the speed star pv the day it came out.