Quit using the term Pop because it doesn't tell me anything. He was still doing "Black music" with duets with Mary J. Blige, Bobby Brown, Ashanti, Jennifer Lopez, Christina Milian, etc.. These songs were getting heavy rotation on R&B/Hip hop stations and Black clubs and venues.
What's weird is I'm looking at the music from early 2000 to 2010 and there's nothing like the current crop of pop singers. It's mostly Hip Hop and R&B.
So...an equivalent from back in the day would be like a rap feature in a Britney Spears or Christina Aguilera or Kelly Clarkson song I guess...which just did not happen.
Summer Songs 1958-2015: The Top 10 Tunes of Each Summer