Soooo mine had to be:
No Scrubs (Remix) ~ TLC--FIRST AND FOREMOST! I was (and still am) gaga over TLC and the vid for this song was amazing but the VMAs were even better. I even memorized the ENTIRE dance with my cousin. I think it was especially cool because 9 was one of my favorite numbers and it was my favorite group performing on 9/9/99 while I was in 9th grade.
http://www.youtube.com/watch?v=p7dJ0aClRuk
All Cried Out ~ Allure ft. 112--whenever I heard this, I dropped everything. It always had a special place in my heart. It was my fav song for awhile and when my sister realized how much I loved it, she told me it was a remake...and that the original had been my fav song when I was little.
http://www.youtube.com/watch?v=8eSXnB2J_q4
Crash and Burn ~ Savage Garden--this song meant a lot to me in high school. It was a total description of my life (to an extent, so was this entire CD).
http://www.youtube.com/watch?v=GgU6UpNjbLc