I totally understand what the OP is getting at.
The reason why it feels like all the fun stopped once the year hit 2000 is because in the mid to late 90's corporations finally figured out how to synthesize and commodify Black culture.
The innovations of Black culture feed directly into America culture as a whole.
Instead of letting the culture grow organically in the Black community and allowing it to spread to the rest of the nation, the corporations are using "influencers" to direct which way they want the culture to grow.
They genetically engineer our culture, so to speak.
The once the product of that influence is fully formed, then they package it and sell it back to us.
The rise of Lil Wayne is prime example of this. The Kardashians as well. Death Row Records.
Then the cycle repeats.
It just so happens that all of the trends and cultural artifacts are destructive and Black people are actively celebrating our own destruction.
Not only that, but we reap only a tiny slice of the extravagant revenue that the culture stream generates.
As a society, we're getting dumber, more crass and unsophisticated, more violent and hedonistic, more cruel, more promiscuous, more unhappy, and overall more gross.
And almost everything you see coming from a mass media source is pushing you further down that path.