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

At the height of the label’s popularity, a pioneering A&R executive took matters into his own hands to help them stand out amidst the city’s crowded but crucial mixtape scene.

By Evan Auerbach and Daniel Isenberg

October 25, 2023

In their new book Do Remember!: The Golden Era 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.

THE IMPORTANCE OF LANDING EARLY JAY-Z MIXTAPE PLACEMENTS

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.

ROC-A-FELLA MIXTAPE SERIES

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.”

Dame also gave us this crazy speech like, “Y’all better get your shit together because we could let people go for this. This is inexcusable. And if you guys were gone tomorrow, what the hell are you gonna do?” That’s when I was like, “I gotta get something going on my own.”

We wanted to do the Roc-A-Fella mixtape and get shit bubbling in the street. We wanted to control the narrative since it was our mixtape. DJs had their own mixtapes, but we didn’t control that. We would just give them records and hope that they got on there.

I was instructed to go to Clue, because Clue was the hottest DJ at the time, or one of the hottest. Me knowing Clue, I just knew he was difficult. He just did things his own way. I wasn’t going to be able to help control the narrative on the tape. I also wanted to put my name on it so I could start branding myself.

So I went to Jay-Z and I was like, “Yo, we gotta do this mixtape. Do you mind if we use Envy? Because Envy does all the distribution for Clue, so we’ll open the same doors. I don’t know if you’re cool with it or Dame’s cool with it.”

Jay was like, “Okay, if Dame’s cool with it, I’m cool with it.” I went to Dame, same shit. “I spoke to Jay, I think we should go the DJ Envy route. Envy is new. He’s hungry. He’s hot. He’s right under Clue. We’d have the distribution and we’re good.” Dame was like, “If Jay’s cool with it, I’m cool with it.” I did the mom/dad thing and kind of manipulated my way into letting them be okay with Envy. That way I guaranteed with Envy that my name would go on it beside his.

Envy was like, “Fuck yeah.” Because at the time for Envy, that was the biggest opportunity of his career. He was doing his thing, but he was under Clue and he was still building. He didn’t have anyone that embraced him to the value that Roc-A-Fella had to do a mixtape series. He was doing his own thing with Splash. So, boom, that’s how the Roc-A-Fella mixtape Empire Strikes Back Vol. 1 came about.

We were on fire. We started the mixtape off with Jay-Z’s “U Don’t Know,” that was brand fucking new. Even today that record rings off. So imagine back then, first mixtape, first song, Jay vocals and ad-libs, talking on the mixtape. That was the birth of the Roc-A-Fella mixtape series.

Original Roc-a-Fella mixtapes.Courtesy of Evan Auerbach

MAKING A NAME

That’s also when Lenny S was born. DJ Envy and Lenny S, that’s how I got my name on there. And that’s how I learned what self-branding was. I tried to make a name for myself, so that God forbid I wasn’t at Roc anymore, I would have something to fall back on. So for me, that was the biggest thing of my career. The irony of it all is that Clue gave me the Lenny S name.

ARTIST ACCESS

What was really dope about making those tapes was we had people coming in and out of the studio the entire time. And for the most part, people doing mixtapes didn’t have that access with artists. But me being in the studio when Cam came through, it was like, “Yo Cam, Jim, we need drops for the tape.” Or, “We need a new song.” Jim Jones, Cam, Beanie Sigel, Freeway, and all of those guys were going in the booth just doing studio quality shit-talking, ad-libs, and songs. I was with them all day, so it was easy for us to get something like “Flipside.”

The mixtapes were ringing off. With the artists, it was almost like, “I want to be on it.” It wasn’t like, “Yo I got a mixtape, me and my man, help us out.” They were meeting us halfway.