Bad example though, because Tragedy is a career criminal and already a felon during Intelligent Hoodlum era. So, as others said, he's still from that element, he was just using his brain. And even War Report era, his music was still smart gangster, as his moniker states "Intelligent Hoodlum." Being from an element but trying to enlighten your peers is still street. Play was a stick-up kid, but still loved to dance and party and did things to escape that other life. The streets at that time were all about doing other things, positive things, to take you out of the poverty mind state.
But the "streets" and the streets Benny is talking about aren't even the same. The streets is simply outside, the voice of the people, and everyone that it's composed of. No matter the era of the time, the music always reflected it, as it is the voice/mind state of what's going on outside. Everyone in the hood isn't a drug dealer scammer robber. The radio hosts, the DJs, the bboys, the MCs, the park/block parties, the neighborhood, the cars are all apart of the culture. This is who moved the culture forward.
Now, what Benny is talking about has always existed, however, it was based on the people - the people of the culture. The nerds were still the magazine writers (Vibe, Source, XXL, Word Up), the VJs (Video Soul, Rap City, MTV Raps), the talk shows (Teen Summit), the radio hosts, but all of these people were from the neighborhood. They just had degrees.
The culture shifted because the people allowed the money to interfere too much. And now what is determined as being the culture is driven by 0s & 1s, and those who control the 0s & 1s; and not the actual people first. What counts as the streets now is that it exists online, because if it doesn't exist there, you pretty much don't exist. That said, that internet geeks that never been outside still make up his fanbase, so he really can't complain.
Just wear regular clothes instead of looking silly like this with these gay pastel colors and ripped jeans.
