Janet Jackson - "Doesn't Really Matter"
Reached No. 1: August 26, 2000 Weeks at No. 1: Three
While few people remember the unfortunate event that was The Nutty Professor II: The Klumps, let alone what was on the soundtrack, this hook will always be remembered as one of pop’s best. Like the aforementioned Aaliyah track, "Doesn’t Really Matter" takes a lot of elements from electronic music and hip-hop and merges them into one melting pot of great pop music.
The video also takes the track and brings it up a notch as only a Jackson could, paving the way for crazy CGI/3D videos that dominated this MTV decade. It cost just over $2.5 million to make, one of the most expensive music videos of all time.
Also, Janet Jackson had a starring role in The Nutty Professor II: The Klumps—she plays Denise, a brilliant scientist and Sherman Klump's love interest.