How Jay-Z and Roc-a-Fella Used DJ Envy to Conquer New York Rap

In their new book Do Remember!: The Golden Age of NYC Hip-Hop Mixtapes, authors Evan Auerbach and Daniel Isenberg trace the history of New York rap through its humblest and most world-alteringly important delivery system— the mixtape. As the legendary cultural ambassador Fab 5 Freddy notes in his introduction, hip-hop’s global takeover began with cassette recordings of parties and live performances passed from hand to hand and hood to hood. By the early 20th century, cassettes had been supplanted by CDs and hip-hop was on its way to becoming a highly corporatized multi-billion-dollar industry— and superstar mixtape DJs like DJ Clue became all-important tastemakers, capable of shoring up a newly-mainstream rapper’s street cred or signal-boosting an underground crew into the stratosphere. In this excerpt from Auerbach and Isenberg’s book, music executive Lenny Santiago— best known as Lenny S— talks about how a 2001 mixtape enabled the rise of Roc-A-Fella Records, the label founded by Jay-Z, Damon Dash and Kareem Burke in 1994.

Lenny S was a prominent Roc-A-Fella A&R who knew the importance of the mixtape. In fact, before he came to the Roc, he worked on Bad Boy’s street team as they were pushing the groundbreaking Bad Boy mixtape series. Inspired by this and some of the challenges happening at the time at Roc-A-Fella, Lenny S took advantage of his in-house connections and teamed up with DJ Envy to start his own Roc-A-Fella mixtape series. This not only gave the label a chance to control their own mixtape narrative, but it allowed him to build his personal brand in the process.


Lenny S: At that time for us, it was monumental. Especially [DJ] Clue—he was only going for the top notch. He was chasing down B.I.G. or Naughty By Nature, or whoever were the top people. Somebody like Jay, he wasn’t B.I.G., he didn’t have a hit record, he wasn’t top of the charts, he wasn’t any of that. He was just an ill, dope, self-contained, self-funded rapper from Brooklyn who hustled prior and got money.

Those Clue tapes spoke directly to the streets, so that was a big deal for us. You had the radio DJs at night doing their thing, but the mixtape lived 24 hours a day on every street corner. So that was important when those things got shuffled down to Baltimore, Philly, and North Carolina.

We depended on the mixtapes because they traveled around the country by getting bootlegged and copied, and by word of mouth. Mixtapes were how we discovered Nas introducing Nature, Clue introducing Fabolous—all those guys we found on mixtapes.


Somebody had a record of Jay’s that they weren’t supposed to have. Long story short, the guy got caught with the record. He had it outside the office and was playing it. Dame found out and was pissed, obviously, because we weren’t supposed to let music leak. He was so pissed that the whole staff got docked because he was like, “One team, one family, one unit. One person gets in trouble, we all get in trouble.”

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