I went back to the late 90's and early 2000's when I was these kids age and looked at different hits, and I definitely did not know what I was singing along to.
In 1999 the one of the top hits was Genie in a Bottle to which some of the lyrics are this:
"I'm a genie in a bottle. You gotta rub me the right way"
"The music's fading and the lights down low. Just one more dance and then we're good to go"
As kids we had no idea what this meant, but I remember dancing and singing to it, it was like our anthem for that year!
In 2001 one of the biggest songs was "Let me blow ya mind" by Eve, here are some of those lyrics:
"Drop your glasses, shake your asses. Face screwed up like you having hot flashes"
"Excitement, glock shots from your stash box
Fuck it, thugged out, I respect the cash route
Locked down, blastin, sets while I mash out"
^I'm 22 years old and I still have no idea what the hell that means.
So it seems as though there were songs then that were risky and kids probably shouldn't have been listening to but I still think there are more today. To prove this here are a few old ladies listening to the song "Drunk in Love" by Beyoncé