When I was coming up in high school (I'm from Massachusetts) everybody was talking about a cocaine spot in Harlem, NY. They said you could go there and buy large amounts of coke, and that you could make a fortune going back and forth buying coke and bringing it back home. But you had to be Black and you had to be "street".
I used to ask people, "what does street" mean?"
They said, "street means you feel comfortable around Black people."
So being "street" doesn't necessarily mean that you speak broken English and walk around with your pants sagging around your thighs with your underwear showing. It just means that you can walk through the hood without feeling nervous. It means you can wear a suit and tie on your way to an office job while walking through the worst neighborhoods without getting nervous.
Just to add on, when Vanilla Ice came out he, "acted Black". But he didn't act like himself when he was around Black people. That's why his career folded after one album.
In contrast, Eminem came from Detroit and had Black friends. The reason Eminem was accepted into Hip Hop is because he felt/feels comfortable around Black people. Think about it. When Eminem was in the studio with Jay Z recording Renegade he had to look Jay in the eye and talk to him face to face or else they wouldn't have been able to record the song. That's the difference between Vanilla Ice and Eminem. Eminem feels comfortable around Black people and Vanilla Ice was trying to something he's not.
If you watch the Ice Ice Baby video you'll notice that he's the only white person in the video, which I guess was supposed to show that he was "hood" or "street", but when it was all said and done, he didn't feel comfortable around Black people.
Edit.
And for the record, that coke spot is still in Harlem and I go there every once in a while when I have extra cash.