HipHopDX: When exactly did Ray Benzino come into the picture?

Reginald Dennis: That part of the tale begins in Boston around 1986, maybe ’87. I wasn’t a part of the story during those years and can only go by what people who were there have elected to tell me. Dave Mays and Jon Shecter were roommates at Harvard and after bonding over their love for Black culture they started a Hip Hop show on the campus station. I think Dave had already been working for the station at that time, selling radio spots to local businesses and figured that there might be some money to be made in the emerging Hip Hop market. The radio show was called "Street Beats" and Dave sold ads to local record stores and I guess Jon was in charge of the music. In time the show became quite popular and Dave, sensing that there more to be done with the market, compiled a list of all of the people who called into the show every week and – as the story is commonly told – put his hands on $250.00 dollars and with the help of a Boston gentleman named Kenny Mac, printed up a one page newsletter that he named The Source. Dave also had a hand in the business of concert promotion and would bring rap groups up to Boston to perform. (Dave once told me that it was at one of these shows that the artists who would one day be known as the Native Tongues first hooked up professionally.)

Along the way Dave met and befriended the front man of a notorious Boston street gang known as The Almighty RSO (Roxbury Street Organization or Real Strong Organization or Rock Shit On or Ray Scott Organization). In addition to their very real dealings in the street, they also sported a rap arm that had been working the local scene for years but had been unable to break through to the next stage. Dave and Ray became fast friends, and because he had at least a foot in the door of the industry, Ray figured it would be worth his while to latch on to Dave. You know, Ray’s a guy from the hood trying to do something meaningful with his life and he meets a silver spoon Harvard guy. It doesn’t take a rocket scientist to figure out that Ray would pick Dave as a suitable horse to bet on. Dave was probably going places in life and Ray decided that he would be going along for the ride as well.

Now Jon wasn’t really with Dave’s new choice of friends. See, unlike Dave, Jon was perfectly happy being a wealthy Jewish kid; and while he loved hanging out with Black people, he never got things twisted up. Dave, on the other hand, hated his whiteness, and sought to prove his coolness by actively seeking out the bottom element of the Black community to associate with. Continued on page 2 »