On the latest episode of “Drink Champs,” N.O.R.E. and DJ EFN were joined by legendary entrepreneur Steve Rifkind and revered sound curator DJ Cassidy.

A Merrick, New York-bred businessman, Rifkind established himself as one of the music industry’s greatest A&Rs over the last several decades. Early on, the rap-exec-to-be worked with his father, Jules Rifkind, at Spring Records. Though it proved to be an essential banner for 1970s funk and soul, Spring also brought Steve to the epicenter of hip hop's commercial origins. The label released what is, arguably, the first rap song ever recorded when it dropped Fatback Band’s “King Tim III (Personality Jock)” in March of 1979. And a young Steve happened to be working promotions for the song.

By the mid-80s, Rifkind moved out West to manage New Edition and forge his own path in the industry. And by the early ‘90s, Rifkind had enough experience and knowledge to launch Loud Records. Home to the Wu-Tang Clan, Mobb Deep, Big Pun, along with countless other rappers and crews, Loud’s run of successes in the 1990s helped cement his legacy as a purveyor of taste and driver of culture.

DJ Cassidy has been a bit more hands-on with everything. Literally. Growing up in Manhattan’s Upper East Side as the son of another industry vet, Cassidy began DJing as soon as he turned double digits. And by the time he hit college, Cassidy was already JAY-Z’s go-to man for getting the party jumping. Heavily inspired by Run-DMC and early hip hop pioneers, the talent continued to work his way up until, eventually, he was the DJ of all DJs, word to Barack Obama, Kim Kardashian, Anna Wintour, Oprah Winfrey, and any A-lister who trusted Cassidy to curate everything from parties to inaugurations. One of a kind in his own right, Cassidy met Steve years ago, and their journeys have been intertwined ever since.

In a special joint episode, they break down the highlights of their respective careers and address how the dots have connected for them both. Check out nine takeaways from the interview below and watch the full episode here.

1. Steve Rifkind on being Tupac’s roommate

Right after Tupac’s era with Digital Underground, the fallen rapper bunked up with Steve Rifkind, who at the time was hired by the newly minted Interscope Records to run promotions for their artists. With that experience in mind, Steve remembered the hustle of Pac and their experience of getting it out of the mud with one another. “He would stay with me. I had a townhouse in Studio City. And he worked. He would come to the office with me, he would pack records with me. And it would be us, this kid Faye Duvernay and our assistant Lisa. And it would be us on the floor, shipping, packing records,” he said. “I mean he was a worker. He worked his a** off.”

2. On Tupac’s beef with Mobb Deep

Though Steve and Tupac maintained a tight relationship over the years, a publicized beef between the late rapper and former Loud Records signees Mobb Deep made the label founder question where he stood with his old pal. That is, until one night, when Tupac cleared the air on the situation. “I went to see Tony Rich at House of Blues one night. And I'm walking through, and I get smacked in the back of my head. I got a bald head. So, I don't know if it's a love tap or a real smack. And it's him (Tupac),” the exec explained. “And I'm looking, and he goes, 'You don't say hello?' And I'm like, 'Man I don't know where I stand with you.' And he goes, 'Oh you're talking about them? I'm just messing with them so I could be relevant.' He loved them.”

3. On artists he could have signed

When asked about artists he wanted to ink a deal with for Loud Records, Steve noted a few notable names he would have added to his roster if things worked out. One of them was JAY-Z. “Dame [Dash] came to the office. We wanted to do the deal and BMG (Bertelsmann Music Group) wouldn't let us do the deal because they were trying to build their stuff up. And they were like, 'It's not gonna happen,’” he said. “But I also had [Irv] Gotti before Lyor [Cohen], and Russell [Simmons] got him. And he'll tell you that too.” How did they get connected, you ask? “It was Mic Geronimo,” he added. “We were gonna sign Mic, but we couldn't get the sample cleared. So, they say timing is everything.”

4. On why he started his own record label

As he built out his career, Steve was employed by several companies and made a pretty penny for those contributions. But when he was approached with the opportunity to start his own label, he declined. That is until his father got in his ear. According to Steve, his dad said, ‘“With the company that you have now, you’re doing extremely well but you're only as good as your last contract. MCA could fire you. Warner Brothers could fire you. You could get fired. And then you're left with your d**k and your hat. With this, having a record company, you own something. You're making money while you're sleeping.’ And I couldn't disagree with him on that.”

5. On how working with New Edition impacted business with Wu-Tang Clan

Steve played a hand in the careers of New Edition and the Wu-Tang Clan, among many other soon-to-be marquee acts. For both the underground rap legion and the R&B stars, he embraced the members of each unit going solo. “The reason why I let Wu-Tang do all their solo records because to me the group was always bigger than the whole,” he explained. “Michael [Jackson] sold more records with the Jackson 5. But when Michael went back for the ‘Victory Tour,’ back in that day, that was the biggest tour in the world, ever,” the exec added.

6. DJ Cassidy on beginning his career as a 10-year-old

DJ Cassidy has been spinning on the 1s and 2s since he was in elementary school. During this discussion, the New York-bred spinner recounted how he got his feet wet in the music industry as a child. “I had to be in front of people. I never enjoyed DJing in my bedroom. I was never a real scratch master; I was never that guy. I was never a turntables guy. I was a party DJ, so it's only so much you could do in your room,” he voiced. “I DJ'd every possible thing that I could and brought my milk crates of my records and my turntables to school. And although it sounds silly, it gave me my first experiences in front of anyone. I didn't value these kids' musical opinions. In fact, I kind of had disdain for it. But as a sixth grade, seventh grade, eighth grade kid, and then into high school, it was a beginning,” Cassidy recalls.

7. On DJ Cassidy’s sense of fashion

DJ Cassidy has a specific look to his character, which is done intentionally after growing up in an era when artists looked like superheroes in their own signature apparel. “I think I started experimenting with hats because of Run-DMC, Jam Master Jay and Michael Jackson… Every kind of bit of my style, I could trace back to someone in something. I wore my pants really short; that's Michael Jackson. Every little bit is some kind of influence in a blender,” he said. “As a kid, I idolized Bobby Brown. He's also become a friend. And he just looked like the coolest person on earth. The leather outfits, I got that from him. So, I've been idolizing people for a long time and a lot of those people are my friends today, but they're still my idols.”

8. On DJing at The White House

DJ Cassidy is the first DJ to spin at the inauguration and at The White House in general. With the latter opportunity in mind, he told a story about performing “Signed, Sealed, Delivered (I'm Yours)” with Stevie Wonder at a party thrown by former President Barack Obama and how he was able to shake the nerves off for the momentous occasion. “I'm cutting up this song, praying that I just stay on beat every four bars. Stevie's rocking. And I kinda turn to my right. And I see JAY-Z and Chris Rock. And they're nodding their head. You know that mean face you make at the studio when you make a beat and the head nod? And I look at them and they see me seeing them and at that moment, all the pressure went off. Then, I was rocking when I saw that and it was one of the greatest moments of my life,” he recalled.

9. On curating the sounds of Beyonce and JAY-Z’s wedding

DJ Cassidy has been called on to soundtrack special occasions for countless famous people. One of the most significant is Bey and JAY’s wedding. “I had already been DJing JAY's parties for at least five years. I got my first call from JAY, I think, when I was still in school, so I must've been maybe 20. And so, I would DJ all his parties: his birthdays, then Beyonce's parties when he threw them, the 40/40 Club opening in Atlantic City and Vegas… So, the call to do his wedding was not at all abnormal at the time,” Cassidy recalls of getting the ultra-high-profile gig. “I don't think there was any talk of music other than the first dance and the entrance song,” he notes of the trust the Carters placed in him as the sole DJ.