Mariah Carey featuring Jay-Z - Heartbreaker (10/9-10/16)
What a weird combination of elements. Jay-Z, Good/Evil Mariah Carey, Jerry O'Connell, Bathroom Kung Fu Fights, Olivia Newton-John Mariah Carey. I mean, this video has everything, doesn't it?
Enrique Iglesias - Bailamos (9/4-9/11)
This was from when he was still mostly known as "Julio's son", if I recall correctly. I think "Hero" in 2001 was what changed that. Let the rhythm take you over...
Britney Spears - ...Baby One More Time (1/30-2/6)
How on EARTH can this late 90's staple have only spent 2 weeks at #1?? That is insane. It feels like this one should have been up at the top for months!
Brandy - Have You Ever? (1/16-1/23)
If "...Baby One More Time" became a staple of 1999 MTV, then I feel like this Brandy song was all over VH1 at around the same time. This is a song you don't hear very often anymore.