9 Things We Learned From ItstheReal's 'A Waste of Time' Event With Roc-A-Fella's Key Players

Jeff Rosenthal, Kyambo "Hip-Hop" Joshua, Kareem 'Biggs' Burke, Lenny S., and Eric Rosenthal
Johnny Nunez/WireImage

Jeff Rosenthal, Kyambo "Hip-Hop" Joshua, Kareem 'Biggs' Burke, Lenny S. and Eric Rosenthal speak onstage during A Waste Of Time Live: ItsTheReal celebrates Rockafella Records at Highline Ballroom on July 26, 2017 in New York City. 

New York City holds a special place in the legacy -- and nostalgia -- of hip-hop’s history, and lately it’s been an enjoyable trend to travel back in time to celebrate that tradition.

On Wednesday night (July 26), rap fans were treated to a two-hour taping of ItstheReal's A Waste of Time odcast, with a slew of playmakers and artists instrumental in creating NYC's legendary Roc-A-Fella Records. Pod hosts Jeff and Eric Rosenthal gathered Kareem “Biggs” Burke, Kyambo “Hip Hop” Joshua, Lenny Santiago, Young Guru, Just Blaze, Freeway, Young Gunz (Young Chris and Neef Buck), Jim Jones and Chaka Pilgrim, all of whom shared insider stories and good memories on a pivotal moment in JAY-Z’s rise from Brooklyn MC to international icon status.

The timing of a Roc-A-Fella appreciation night couldn’t be better. Hov just released his thirteenth studio album, 4:44, which remains at No. 1 on the Billboard 200 chart for a second straight week. Jay continues to remain culturally relevant and consistent, whether calling out the rap game for their money-phone selfies or tapping into some personal revelations on his family (Beyoncé, Solange) and friends (Kanye West), Hov's growth as an MC further proves he's undisputedly among the best to ever do it.

While it is a tough task to condense years of musical excellence into a two-hour block, the star-studded event produced several new stories and anecdotes from The Roc's incredible run. Here are nine things we learned from those who helped create and define one of hip-hop’s most storied record labels.

Roc-A-Fella amusement parks were almost a reality

Biggs, who co-founded the label alongside Dame Dash and Jay, spoke about Dash’s vision for Roc-A-Fella during its early formation. Besides devising plans to break into hip-hop, there were talks of branding Roc-A-Fella in industries outside of entertainment. “Reasonable Doubt was the platform that we used, but we knew that we would use that platform for fashion, films,” Biggs said. “We talked about tech and spirits and also sports.”

These big-picture thinkers even went as far as amusement parks. “We talked about having a Roc-A-Fella Great Adventure: The Roc Venture,” Biggs said, adding if they saw the idea through, it would have started in Harlem. Ah, what could have been.

JAY-Z once freestyle battled LL Cool J (and won)

One of hip-hop’s greatest stories is the near-mythical freestyle battle between JAY-Z and DMX that happened at a pool hall somewhere in the Bronx in the 1990s. At the time, JAY-Z was affiliated with a group called Original Flavor, while X was aligned with Harlem Knights. Organized by Biggs’ friend Steve Mack and taped by the late Big L, it was a friendly battle-of-the-boroughs competition that was so close that you could argue who won for either side.

A battle-tested Jay was ready for anyone. “Jay went to battle any time,” Biggs said. “He would walk around with money in his pocket, try and battle people. I wasn’t there, but he battled LL." Though Biggs admits he didn’t see it firsthand, he claims Jay won, off the strength of the verses he heard afterwards.

JAY-Z and The Notorious B.I.G. learned in the studio together they neither MC wrote their rhymes down

The period while Jay’s recorded his first album, Reasonable Doubt, was when Roc-A-Fella got close with Biggie. The earliest interaction between the Roc and Bad Boy happened on the video shoot for Jay’s song “Dead Presidents,” when Big stopped by for a visit and famously matched Cristal shots with Dame in a drinking battle.

Eventually, Biggs and Dame were able to get them in the studio together to create “Brooklyn’s Finest” (a request from Biggie) -- a rare collaboration between the two, and interestingly enough, Hip Hop’s first experience in a studio ever. “I remember the engineer came and dropped the pad in front of them,” Biggs says. “And Jay pushed the pad to Big, and Big pushed it back to Jay. They both looked at each other, and that’s when they found out they don’t write.”

DJ Clue wanted Roc-A-Fella to sign Fabolous

Back when Roc-A-Fella was a modest operation of about 10 to 12 employees, there were several people who would come in and out of the office. According to Biggs and Hip Hop, Jay would be there every day. “We was so excited, that was our first office,” says Biggs. “Being in there, everybody would just want to come every day.”

Biggs says Roc-A-Fella held meetings with DJ Clue, who wanted the label to sign Fabolous at the time. Others who came through were Irv Gotti, who was working as Jay’s DJ and as a producer, before he gained fame running the record label Murder Inc. which broke through after the success of Ja Rule. “Irv was always that guy that believed he was motivational,” Biggs said. “Irv did ‘Can I Live?’ That’s one of the staple songs on Reasonable Doubt. He always had great input and insight on how to support the movement and push the culture as well.”

Kanye West’s beat tape for The Blueprint originally had songs for Ghostface Killah, DMX and more

It’s common for producers to shop around their beats to different rappers. But The Blueprint’s sound took a new direction thanks to Kanye West and his beat tape, which included instrumentals that became “Takeover,” “Izzo (H.O.V.A.),” “Heart of the City (Ain’t No Love)” and “Never Change.” Hip Hop revealed ‘Ye would make beats for specific people at the time. “‘H to the Izzo’ was for Ghostface. ‘Ain’t no Love’ was for DMX. ‘Takeover’ was for Beanie Sigel. Cam [Cam’ron] got ‘H to the Izzo,’ too,” he said. Just Blaze dropped another gem by noting Prodigy was the first to rap over “U Don’t Know,” before Jay got his hands on it. And Lenny S revealed Memphis Bleek turned down “Whoa!” and “Oochie Wally,” which became huge hits for Black Rob and Nas, respectively.

Roc-A-Fella bred entrepreneurship

Chaka Pilgrim made a brief appearance to talk about Roc-A-Fella’s venture into films, her stories of rap group State Property and the label’s entrepreneurial spirit. At the time, she was working for U.S. Citizenship and Immigration Services, but would spend her off hours building the Roc’s fan mail club with her best friends.

“Everybody that was in charge was already an entrepreneur in the street sense of the word,” she remembered. “They really believed in all of us making our own money and hustle. They were really supportive of us all starting our own company. If you look back at the history of the people who worked at Roc-A-Fella, almost everybody at one point or the other had their own business. Our business at that time was the fan club and we promoted it. We basically springboarded our own little careers from that building.”

“Flipside” was one of the original JAY-Z and Beyoncé records

While the panel was on the topic of Freeway’s debut album, Philadelphia Freeway, and how monumental it was for the label and his career, Just Blaze shared another tidbit about his song “Flipside.” The song was an early contender for the first Jay and Bey record -- a “Roc the Mic” for Beyoncé, if you will -- but Free and Just were so in the zone that “Flipside” became a reality for the Philly MC.

The four biggest songs on Roc-A-Fella were…

According to Biggs, the label’s four biggest songs were Cam’ron’s “Hey Ma” and “Oh Boy” (both top five records on the Hot 100) and Young Gunz’ “Can’t Stop, Won’t Stop” and “No Better Love.”

Dame Dash doesn’t get enough credit

Despite Dame and Jay’s highly-publicized falling out over the years, the group couldn’t say enough about Dame’s influence on the brand he helped co-create. “I think he made everybody believe in themselves,” Biggs said. “If he can do it, you can.”