The Legacy of Bad Boy Entertainment

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Bad Boy Entertainment founder, P. Diddy (via Shutterstock)

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This week’s episode of Trapital is our breakdown of Bad Boy Entertainment. It’s the next podcast in our case study series. I’m joined by Zack O’Malley Greenburg, who wrote 3 Kings and shared several stories from his work for that book.

can’t stop won’t stop, the motown – bad boy comparisons

Puff Daddy’s Bad Boy Entertainment and Berry Gordy’s Motown Records have been compared countless times, but let’s dig into that.

Motown created a new genre. Gordy convinced the industry gatekeepers that music made by Black artists wasn’t just for Black people. There was a formula, and it worked.

Bad Boy also had a distinct sound, but several 1990s record labels did too. Death Row Records did the same with G-funk. So did Cash Money, No Limit, LaFace, and So So Def. They all had in-house production teams that turned soul samples into modern anthems.

The real tie between Motown and Bad Boy is the ability to maximize derivative work.

When Marvin Gaye’s “Ain’t No Mountain High Enough” became a hit in 1967, then ran it back three years later with Diana Ross’ version, and it became an even bigger hit. The Jackson 5 did several successful Motown covers. Motown would even have the same artist do two different versions, like Martha and the Vandellas’ two versions of “Jimmy Mack.” The list goes on.

Bad Boy did the same with remixes. It’s debatable whether Bad Boy actually invented the remix, but the hits delivered. When Puff was at Uptown Records, he turned Mary J. Blige’s “Real Love” remix into a completely different song featuring The Notorious B.I.G. Years later, Craig Mack’s “Flava in Ya Ear” remix was the song that closed the deal for Bad Boy and its 50-50 deal with Clive Davis’ Arista Records.

Bad Boy had a similar approach with its “Part 1” and “Part 2” of songs like Busta Rhymes’ “Pass The Courvosier” or Diddy’s “I Need a Girl.” That formula had Berry Gordy’s name written all over it.

If Gordy and Combs built Motown and Bad Boy today, they would be all over AI music. There would be an AI artist named “Marvin GAI” with its own spin on “What’s Going On.” Bad Boy would have created an AI artist named “MAIse” to replicate the real Ma$e. It was all inevitable.

You can listen to the episode here or read below for more highlights.

building something bigger than yourself

Here’s an excerpt from Puff’s 1997 interview with The Los Angeles Times:

In the past, many recording artists have dreamed of becoming moguls, but no one has reversed the process. Imagine Motown founder Berry Gordy putting out his own album and becoming as big a recording star as Marvin Gaye or Stevie Wonder.

Sound ridiculous? Not to Combs.

“I know it’s a very weird career move, but I take it very serious,” … “At first I thought nobody would accept me as a rap artist. After all, it’s not like I came from the hood. But you know what? It’s all in how you market yourself.”

This move became a blessing and a curse.

The blessing is that Bad Boy reached greater heights in the immediate years after Biggie’s death. Biggie’s Life After Death—released 16 years after Biggie’s death— went diamond. Puff Daddy & the Family’s No Way Out went 7x platinum. And Mase’s Harlem World went 4x platinum. Puff was on top of the world in 1997.

By summer of 1999, Bad Boy had sold more records in that fiscal year than Madonna’s Maverick (during her “Ray of Light” era) and more than Def Jam when DMX and Jay Z were on top. They were in their bag.

But as Puff’s star rose, the rest of the Bad Boy roster took a backseat. Faith Evans and 112 wanted off the label and had rumored financial disputes. Mase has been at odds with Puff for years over financial disputes. Other artists like Shyne, G. Dep, and Loon had legal troubles. By 2002, the only Bad Boy artist with a platinum future was Puff himself. Despite a few bright moments, like Diddy’s Press Play, Danity Kane, and “I’m Coming Home,” the label couldn’t recapture that 90s glory.

In hindsight, Bad Boy’s journey was inevitable. Puff has always been a brilliant marketer. His biggest skill is marketing his own lifestyle. He did it with artists like Jodeci (at Uptown), 112, and Mase. They were modeled as extensions of Puff. He did it with female artists like Faith Evans, Total, and Cassie (who eventually became his long-term partner). And he did it with products like Ciroc and Sean John.

That mentality can scale consumer products, but it’s hard to scale creative talent with the same longevity. Puff did it well with his own artistic brand, down to the frequent name changes, TV shows, and guest features. But without another Bad Boy leader as his peer, who isn’t “all in the video” and can think beyond the flagship artist, there are only so many resources to go around to develop an entire roster.

It reminds me of my conversation with Dreamville’s CEO Ib Hamad. I asked him how the label separates its brand from J. Cole. It’s hard as hell to do, especially today, but it helps that Ib isn’t also trying to build his own artistic career.

It’s no different than a startup with a technical co-founder and a front-person as the other co-founder. Doing both isn’t impossible, but it’s not easy.

a “what if?” for Bad Boy and Roc-a-Fella

The first single that The LOX released on Bad Boy was “If You Think I’m Jiggy.” Please take a minute and listen to this track.

It’s a decent song but not the right fit for Jadakiss, Styles P, and Sheek Louch. It was an attempt to fit The LOX into that Bad Boy brand. This is why Kanye West said, “I feel like Bad Boy street team, I couldn’t work The LOX.”

The LOX eventually left Bad Boy. Jadakiss and Styles P dropped successful solo albums, and it all made more sense. This is what these emcees should have been on the whole time.

On the podcast, Zack brought up a great point.

He said that there should have been a record label trade: Bad Boy should have traded The LOX to Roc-a-Fella in exchange for The Diplomats. Songs like Cam’Ron’s “Oh Boy!” and “Hey Ma,” or Juelz Santana “Oh Yes” made a lot more sense with Bad Boy’s swagger. Meanwhile The LOX had more in common with the grittier, State Property, Hard Knock Life vibes that Roc-a-Fella had at the time.

The music business doesn’t work like that, but what if it did? Who says no to that trade?

It would have added a whole new element to the LOX vs Dipset Verzuz battle.

Those are just a few topics we dive into. We also discussed:

– lessons learned from Uptown Records’ Andre Harrell
– the impact of east coast vs west coast beef on Bad Boy
– the money made and the deals signed

Listen here


[00:00:00] Zack Greenburg: Diddy’s ability to sort of walk the line and step back, you know, I think that’s what ultimately kept Bad Boy in the position that, you know, that stayed and kept him in the position that he continued to be in. 

[00:00:09] Dan Runcie Outro Audio: Hey, welcome to the Trapital Podcast. I’m your host and the founder of Trapital, Dan Runcie. This podcast is your place to gain insights from the executives in music, media, entertainment, and more who are taking hip hop culture to the next level.

[00:00:35] Dan Runcie Guest Intro: Today’s episode is another case study style breakdown, and this time we chose to dive deep on the one, the only Bad Boy Entertainment when it comes to branding and when it comes to marketing. I don’t know if there’s another record label that has as identifiable as a sound of vibe as bad Boy, you knew what that vibe was.

Puff said it himself, they take hits from the eighties, but do it sound so crazy? And that was the formula, and it worked time and time again. What Puff did was smart, it was a modern approach to how Berry Gordy approached the record business with Motown. But then he put his own spin on it, interning with Andre Harrell at Uptown Records, learning from him and then putting his own spin on it even more, making it relevant for the 90s and truly becoming the icon that was synonymous with shiny suits with that Bad Boy flavor.

And so much of the success of one of the best MCs ever, the Notorious BIG, some of the most iconic R&B groups at the time, and singers such as Faith Evans, 112 and many more. And plenty of artists that unfortunately also had plenty of challenges and issues when it came to payment, drama, legal disputes and more.

And we dive into all of that. I’m joined again by Zack O’Malley Greenburg. He wrote a book called Three Kings, where he dived deep into Diddy, as well as Dr. Dre and Jay-Z in this book, so he’s well-versed and shared a bunch of great stories in this one. So let’s dive in, really excited for this one. Hope you enjoy it.

[00:02:06] Dan Runcie: We are back to talk about the wondrous world that Sean Combs built himself Bad Boy entertainment and joined by the one and only Zach Greenburg. Welcome back

[00:02:15] Zack Greenburg: Oh, thanks for having me, Dan.

[00:02:17] Dan Runcie: Bad Boy is so fascinating because Puff is someone who has in many ways been this larger than life character even before people knew him externally as that.

And he has really stayed true with that throughout his time in hip hop and even before then. And most people know the origin story starting back in his days at Howard. But I think based on the research you’ve done, I know you have some backstory with some of the lessons and some of the things he did even before that.

So walk us back. Who was puff in the early days before the world? Got to know him.

[00:02:52] Zack Greenburg: Yeah, I mean, you know, I think the funny part is that, that puffy was always puffy and, you know, it just took a while for a little while for the world to kind of figure it out. But you know, there are these kind of consistent themes when you go back through his youth and you, kind of get a sense of who he was.

And, you know, I remember writing my book Three Kings, you know, Diddy being one of these kings, talking to people who grew up around him. He really was that same guy from the very beginning. So even when he was a kid, you know, he spent his very earliest years in Harlem, but then moved to Mount Vernon, kind of a suburban neighborhood.

you know, just north of the city limits. And you know, he had not just one paper route, he had multiple paper routes and on every, you know, every route. He had this philosophy of like, he wasn’t just gonna take the paper and fling it into the family’s yard. He was gonna get up and he was gonna go, you know, open the screen door and put the paper in between the screen door and the main door so that people didn’t have to go up and do so like he was, you know, that dedicated, that hardworking from the very beginning. you know, I think another story I learned from his youth, Puffy was like, there was some, Some debate, you know, some kid had a pool party and, Puffy wasn’t invited. there may have been some racism at play, we don’t know. But anyway, Puffy’s solution was to convince his mom to build a pool in their backyard and then start his own pool parties and, you know, I mean, it’s like the most puffy move ever, right? So he just ended up finding, you know, wealthier and wealthier backers to build the proverbial pool as the years went on.

[00:04:23] Dan Runcie: That is the perfect story to encapsulate him because I feel like I could imagine other people having white parties. He doesn’t get invited to the white party, so he’s like, all right, bet I’m gonna go start my own white party. And now it’s this annual thing, however many years running.

[00:04:37] Zack Greenburg: Exactly. I mean, and you know, you know, as you kind of trace his evolution, you know, in between it was the same thing. So, you know, we all know the Howard Days, he was taking the Amtrak up, sometimes hiding in the bathroom, so they didn’t have to pay for the tickets. He didn’t have any money but, you know, he would go up back up to New York on the weekends, he would plan these parties.

He started to build a name for himself. and it was exactly that, you know, so from the pool parties, in Mount Vernon to the parties that he was throwing, you know, his colleges to the White party, you get that through line of Puffy that, you know, kind of continues all the way through, through the Ciroc era, you know, I think, which really makes this sort of art celebration, ethos, you know, all the more credible, right.

[00:05:16] Dan Runcie: Right, and you mentioning him taking Amtrak. Of course, that’s him going from DC to New York to go to Uptown Records where he pushes and fights to get his unpaid internship. Working with Andre Harrell, who was on the Ascension himself. He had started that record label in the mid to late eighties. He then sees the rise.

He’s early on, new Jack Swing has so many of the early folks making that sound there. And then Puff comes in, he sees a opportunity to elevate and position that brand because the whole thing that Uptown was about, they were trying to push Ghetto Fabulous. They wanted to show that there was a opportunity for people who grew up with nothing to feel like they had that release.

And Andre Harrell, he since passed away a few years ago, but he spoken about this a few times and you can see how Puff at the time adapted a lot of that. He worked with Jodeci. He was so integral with how he styled them and making sure they had the right jackets. And at the time, Jodeci was very much seen as this alternative to Boys to Men, Boys to Men was a bit more buttoned up.

They made music that was G-rated that you could play everywhere. And Jodeci definitely leaned into the sex appeal, which is something that we saw continue play through with. Bad Boy records of Bad Boy Entertainment in the future. He did similar with Mary J. Blige, taking her from just being a R&B singer to giving her more of a hip hop Ben, and doing a bit more of that crossover vibe, which is something that we saw again with Bad Boy too.

And as Puff continued to show his influence, things started to clash because the intern then becomes VP of A and R, and that VP in A and R starts to butt heads and really challenge Andre Harrell on a number of things.

[00:07:06] Zack Greenburg: Yeah. And, you know, I think, you know, like you said, Puff really had an idea of what Uptown could be that was, you know, a little bit different from Andre. But it really worked, right? It was the idea that it was, it had a little bit more of an edge to it. you know, like Jodeci had a little more edge than boys to men.

you know, that every artist that was gonna be out on Bad Boy would have like, you know, would have that level of class, but also would have kind of like, you know, kind of like a street smart edge. And so, right, it was like the Tims and the backwards hat, but, you know, maybe you had like a nice jacket.

It was that kind of mix. And it was very much like in line with Puffy himself. and I think, you know, it’s a theme that you kind of started to see. as kind of, he moved on, you know, whether it was Bad Boy or Roc or whatever it was, the thing was synonymous with Puffy. Puffy was synonymous with the thing. But as he began to later on build these assets, you know, he could sell the businesses in a way that he couldn’t sort of sell his own image and likeness necessarily. So, that started with, Uptown for sure, it was Andre’s thing, but it started to feel like it was Puffy’s thing.

And I think there was some thought that, you know, that there sort of couldn’t be two kings in the castle. And Andre eventually pushed him out and, you know, that kind of left it, the Diddy, you know, in his early twenties kind of figuring out like, Hey, you know, what am I gonna do next?

 How am I gonna really start my own thing here?

[00:08:22] Dan Runcie: And I have this quote from Andre. This was from a documentary a few years later. He says, when Puff got fired, he was on payroll and his artists were on payroll. He’s still recording his artists, but he was able to find the best deal, so we never fired him to hurt him. But he fired him to basically make him rich.

I will say that quote is much nicer than certain things that Andre said immediately after that firing, especially in the 90s. But it was cool to see the two of them find opportunities to continue to work together after that. But I think the key thing from his time in Uptown is that he was able to find and work with art is that eventually he started working with on Bad Boy.

That’s when he first works and discovers Big. That’s when he first works and really begins to hone in on that sound. And then he officially launched Bad Boy in 1991, but it really wasn’t until 1993. He starts working with Big, he starts working with Craig Mack and then it all leads up to this deal that he ends up signing with Arista records to officially do this joint venture with Arista.

Arista, of course, was run by Clive Owen, legendary music executive, and they do their 50 50 split. And as the story goes, Clive was on the fence. At first he wanted to hear more, but then Puff Plays flavor in your ear. Craig Max first single, and he was like, all right, I need to be part of this, whatever it is.

So that was the song that took things off and made it happen.

[00:09:50] Zack Greenburg: Yeah, I mean, Clive Davis, of course, you know, legendary, record men, you know, discovered Janice Joplin, Whitney Houston, Puffy, like you could say, he discovered all these people. they were, they were kind of there already, and, I sort of suspect they would’ve had their success even if it were not for Clive Davis.

But, you know, that, we could debate that. But, know, Clive Davis certainly had an eye for talent, one way or the other. So, I mean, I think what’s really fascinating too is, you know, you got think where Puffy was at that point in his life before he got that deal. He was shopping Bad Boy around right?

To a bunch of different labels and it says so much about him and his whole ethos, the way he approached it, and this was another anecdote that I found in my reporting, by one of the founders of The Fader who happened to work at EMI at the time. He was in the room when Puffy brought the Bad Boy deal, to the folks at e Emmi and, you know, so like, just to refresh, here’s Puff early twenties, just been fired.

Just had his first kid, I think. And also, you know, he’d been a part of, this charity basketball tournament at City College where a bunch of people got, crushed in a stampede. He was ultimately found, you know, not guilty of any kind of criminal charges or anything, but his name was all over the papers.

Like there’s a lot of negative press around him. He was kind of, you know, almost radioactive at this point, or at least one might have thought that turned out he wasn’t. But, so anyway, he goes into this meeting with e Emmi and, you know, Their big thing was, Vanilla Ice. And he sort of goes into this meeting and he’s like, that dude’s corny.

Like, I have no interest in anything having to do with Vanilla Ice. Let me tell you how to run your business. And, you know, so he proceeds to like, give them this vision. And then at the end of it, I mean, and I’ll read the quote cause it’s just so good. he says, when you guys get in a room with all them suits and you’re gonna decide what you’re gonna pay Puff, just when you get to a number that you think is gonna make Puff happy, I love how he was referring to himself the third person, right?

He says, get crazy on top of that. And then when you’re there, I want whipped cream and a cherry on top. and this is the best part, he goes, I don’t even want to think about the money. That shouldn’t even be an issue. Don’t be coming at me with no n-word money. Goodbye. And like that was vintage puff.

Like that was billionaire Puffy. Before he was billionaire, before he even had. Like before we had a company. So, you know, I think there’s just such a great lesson in there, which is kind of like, you know, the sort of, if you can pull off the, fake it till you make it, if you can have that kind of swagger. And to be fair, not available to everybody and like, you know, don’t try this at home, kind of if you don’t have it.

But man, if you can pull that off, if you have that kind of confidence in yourself, you can accomplish some pretty incredible things. He didn’t even, you know, end up going with EMI but I think he made a similar pitch at Arista and, you know, and that ultimately got him the deal, that created Bad Boy and, you know, that was really the engine for so much of, what he ended up achieving as the years went on.

[00:12:46] Dan Runcie: That story is one of the reasons why he has lived on to become meed and in many ways become a bit of a gift himself. Whether you look at the Chappelle Show skit where, Dave Chappelle is making fun of making the band, and he has that whole sketch about, I want you to get me some Cambodian milk from a goat, or whatever it is.

And it’s something that sounds completely absurd, but one, it sounded like a lot of the shit that he would say in that MTV show make in the band. And it sounds exactly like that quote that you just shared from that story. The difference is he did this, whether it was for pure entertainment on a show like making the band or when there was really things at stake, like he was at this point when there wasn’t a deal in place, he was recently fired.

But regardless of whether he’s up or down, trying to get it still the same guy.

[00:13:39] Zack Greenburg: Absolutely. You know, and I think it just kind of goes to the point like, did he creates brands. He is the brand. He imbued the brand with his essence. And then the brand becomes that much more valuable, whether it’s a brand that he can sell, you know, for some huge gain, or whether it’s a brand that is compensating him, you know, handsomely for his association or in some cases both.

 That’s kind of the formula and, you know, not everybody can pull it off because not everybody has a brand that is that clear.

[00:14:11] Dan Runcie: And let’s dig into this because I think this is one of the things that does set him apart. Denny used to be a club promoter as well. And this is a persona that we’ve seen oftentimes in music where the club promoter or the party promoter works their way up to then become the executive. You see it now with Scooter Braun, someone who’s a billionaire now, or close to it in his own right.

And he was a party promoter in Atlanta. You saw with Desiree Perez who now runs Roc Nation. She was a party and a club promoter before as well. And you’ve seen it plenty of times before and I think there’s a few things there. There’s a hustle and a relentlessness that you need to have to make that work.

You need to create momentum around some of that isn’t there. You need to understand and be tapped into what people want to hear and what people wanna do and how people wanna feel entertained and how they wanna leave from something feeling like, damn, I had a good time. We need to go do that again. And that is a lifestyle and what Puff did was aligned himself by building businesses that allowed him to do that. Some of those businesses worked better than others, but I think that is the key through line there. On the flip side, I do think that some of these operators and business leaders can often struggle with the bigger picture because there’s so many more elements to building companies outside of the marketing brand promotion and those things, and I think we can get into some of that here because I think we saw some of those dynamics play out with Bad Boy as well.

[00:15:39] Zack Greenburg: Yeah, for sure. And you know, I mean, I think one of the things about Bad Boy is it wasn’t like this was the first record label to develop an ethos and kind of build a lifestyle around it. And, almost like, assembly line, right? I mean, Puffy was doing that himself at Uptown before he just took that same idea and, Pufified it even more.

But, you know, I would kind of almost liken it to Motown. I mean, if you look at, Berry Gordy’s role, I mean, you see Berry Gordy, credited as a producer on so many, of those songs and, you know, he wasn’t like the only person in the room, producing right? he was putting together the right songwriters, the right musicians, everybody to be in the same place. And he was tying it all together with this kind of Motown ethos. And when, you know, when you had a Motown record coming out, you knew what it was. And I think that’s why people in the old days used to be fan people would be fans of like, specific labels, right? They’re like, I like the stuff that this label puts out, you know, I trust them. It’s almost like, you know, I don’t know, you know, Coachella sells out, even before the artists are announced because you know what you’re gonna get if you like Coachella and you just trust that that’s what’s gonna happen. That’s what it was like, Motown, that’s what it’s like with Bad Boy.

So I think Diddy really followed that model that he was going to be the person, you know, sort of putting things together, you know, maybe he was going to, do a guest verse here and there. Maybe he was gonna be more involved in the production of this play of this song or another song. but it was really more in the vision and the ethos of the brand, the Bad Boy brand, what that looked like, what success looked like, you know, the Diddy version of success looked like maybe a little different from the Uptown Andre Herrell version. And, you know, it was like, like a little more swagger, like, you know, like a little more edge to it. And he was really able to kind of like, make that tangible. So, you know, I would keep going back to that as like something that sets him apart, you know, following the footsteps of the likes of Berry Gordy and 

[00:17:34] Dan Runcie: The Motown example is good because they also were able to maximize the most from the broader roster they had from the hits that they had Berry Gordy, of course, was famous for one artist on his record, has a huge deal. Okay, we’re gonna get another artist on that record on that label to then do it again.

You saw that with Aint’ No Mountain High Enough. Marvin Gaye has his version that goes through the roof. Okay, let’s get Diana Ross to do her own version, her own spin on it. That becomes a song in its own right. And you saw, did he do this to some extent with remixes? How one artist had the remix that worked out well.

Okay, or one artist had the original song that worked out well, okay, let’s get the remix now. Let’s get the whole Bad Boy crew on this remix to go do their own verse and do this thing. They did that time and time again, and then in the early two thousands he had that album. We invented the remix, and there’s plenty of debate on whether or not they actually did invent the remix, but that remix that they did of Flava in Ya Ear with, Craig Mack, and they had Biggie on that one as well. That is one of the more classic iconic remixes that people do go back to. And I think the other way that they’re , similar too is some of the disputes that artists have had about pavements and things like that, which we can get into eventually.

But that’s always been the model. I think there in many ways, you’re right, it’s more like Motown than it is like uptown.

[00:18:58] Zack Greenburg: for sure. And you know, on the Biggie point, I mean, people forget sometimes, but Biggie was originally signed to Uptown and Puffy had to go and get him back, and I think they were able to negotiate his release or his transfer of his deal from Uptown to Bad Boy for something like half a million dollars, which, you know, turned out to be, a pretty good deal all the way around.

So, you know, he knew that sometimes he would have to shell out and, you know, he did from time to time. That certainly didn’t stop there from being disputes, as time went on. But, you know, I think one of the other fascinating things is sort of this interplay, you know, he really walked this line, of sort of like, you know, the corner in the corner office, right?

you know, the boardroom, and the street, and, he played up this sort of like lineage that he had of the Harlem gangster world like his dad, Melvin was an associate of Frank Lucas from, you know, the subject of American gangster. And you know, like his dad was known in Harlem. I think they called him, pretty Melvin.

Like he was very flashy, you know, he always had the best suits and, you know, and all that kind of thing. But, you know, he definitely came from that sort of like grand gangster era. you know, Frank Lucas and Nick Barnes and all those guys. I mean, that was sort of Puffs lineage.

And he definitely played up and he certainly played up, you know, sort of different sort of, street edge, you know, when things got heated in the Bad Boy Death Row situation. But at the same time, he never really wanted to go too deep into it.

And I talked to somebody who sort of grew up around him, and he called him Jimmy Clean Hands, you know, because he didn’t really want to get like, like he used the association. When it was sort of convenient, but also he didn’t want to get too deeply associated, with that side of things.

So, to me it’s, a really fascinating tightrope walk, how he pulled it off. And, if he’d gone further, toward that side of things, I don’t think that would’ve ended well for him. And if he hadn’t gone quite as far as he might not have had, you know, a certain credibility or an edge that, you know, that contributed to so much of the success of Bad Boy, especially in those days.

[00:21:04] Dan Runcie: And he did it at a time in the 90s when it was easier for hip hop stars to be able to control the narrative and push what they wanna push and not have other things cover or not have other things be uncovered, or all these internet rabbit holes. I could imagine him trying to do this 10, 15 years later, and it could be a situation like Rick Ross where all of a sudden there’s photos of you as a correctional officer popping up on the internet and people are like, bro, what the hell’s going on here?

I thought every day you were hustling. I could have seen something like that happening the same way that Diddy, but by the time that plenty of people have had those debates about, oh, well, you know, Diddy was actually a kid that grew up in the suburbs and went to college and X, Y, Z, and there’s plenty of ways that you could flip that story, but by the time that even became a discussion point, at least in circles where I heard him growing up, he was already an established star.

So there was really nothing else that you could do at that point.

[00:21:58] Zack Greenburg: yeah. And I guess he could walk that line because he really did kind of embody both, right? Like he was the son of a, you know, a Harlem gangster. he was born in Harlem. His dad was killed, you know, on I think Central Park West and 108th Street or something, you know, in a dispute a case of I think mistaken identity.

I mean, so there were real, you know, tough things that, he was born into. And at the same time, he was also, you know, like the college dropout. Like you know, he went to school, he did his thing like, you know, you could say he was like a proto backpack rapper in some ways, like if you wanted to spin it that way.

And he kind of embodied both of these worlds, but I think that really, if he hadn’t actually lived both those lives, it would’ve been harder to sort of embody them simultaneously as he did.

[00:22:47] Dan Runcie: And even in him, in his own right, there were many incidents that he had that people felt could have supported this narrative that he wanted to, for better or worse, whether it was the 1990 Club nightclub, the 1999 nightclub shooting after the Nas Hate Me Now Music video, him and his team going into Steve Stout’s office and then, you know, assaulting him.

And then everything that came up after that, or even as recently as within the past 10 years, the incident at UCLA with the coach yelling at his son. There’s been plenty of things that have came up that show, you know, that the relentless, the temperament that could often work against his advantage as well.

[00:23:26] Zack Greenburg: Yeah. I mean, you know, didn’t he bash Steve Stout over the head with a champagne bottle or something? I mean, you know, but what’s that line? We back friends like Puffy and Steve Stout, you know, like it, 50 cent had that line. I think he has a remarkable ability to, you know, to end up being sort of friendly with, people who he had these disputes with in the past.

So, you know, whether, Steve Stout or, Shine or whoever, like, he finds, various ways to, sort of bridge divides in the end. I don’t know how it turned out with the coach from, was it UCLA, or USC. But I suspect that’s fine too. but yeah, he does find a way of patching things up.

[00:23:59] Dan Runcie: No, he definitely has and we could talk a little bit more about some of the disputes that came with some of the artists, but I do wanna talk a bit about the business of Bad Boy itself and how it went about things. And one of the things that we saw from successful record labels, of course, Zach and I have done past conversations on Cash money, and Roc-A-Fella, and they’ll always find innovative ways to work within their constraints or find ways to make things work even when you don’t have all of the resources in the world.

And one of the things that Bad Boy did was they really leaned into sampling and sampling hits from the eighties and making them the most successful things they could be. What’s that line from that May song Making, taking hits from the eighties make ’em sound 

so Make it sound so crazy. Yeah.

so they have their in-house production as well with hit men who then do most of the production, and they give you that Bad Boy sound that you can identify when you hear it immediately on a song, whether it’s a total song or it’s a one 12 song.

And they were able to do that and that formula worked so well because you had this generation that grew up listening to those songs because their parents heard all those songs as well. These are black music classics and then they were able to repurpose them and because of the time and things weren’t quite as oversaturated, it sounded quite authentic in a way where I think even some samples now can feel almost a bit forced because you can be like, okay, they’re really trying to work that artist.

And who knows? I might be also looking at this now, someone in my thirties as opposed to in the 90s, looking at it as someone that’s growing up experiencing this. But still, I do think that there was a bit of like a authenticity and a vibe that they were able to create with each of those sample tracks.

And plenty people tried to do it. Of course they didn’t invent it. I know that Death Row and NWA, Dr. Dre had done it successfully before Diddy, but Diddy and Bad Boy were definitely able to put their own unique spin on making that as effective as it was.

[00:25:57] Zack Greenburg: Yeah, definitely. I think, you know, I mean, I think to your point, but it, like it really opened up this sort of aspect of mainstream hip hop when, you know, maybe there were some radio stations that weren’t gonna play some of these songs, but, you know, like a puffy song or a biggie song ordinarily, but, you know, if you have like, Oh, that’s David Bowie in the background.

Like I’m familiar with this. then, you might be sort of like more inclined to put it on the radio if you were a certain kind of dj, which then might reach a certain kind of listener who didn’t, you know, ordinarily listen in hip hop and, you know, and you kind of have this, kind of snowball effect.

you know, sure.

[00:26:32] Dan Runcie: And then from a personal perspective, I’ll be the first to admit the amount of songs that I had heard the first time as Bad Boy Version. And then growing up, you then later hear the original one that they sampled from the eighties or seventies, whatever Disco tracker, soul Tracker was, and you’re like, oh, that’s what that song was from.

It’s happened endless times and it continues to still happen.

[00:26:54] Zack Greenburg: Yeah. I must confess, I heard I’ll be missing you before, I heard I’ll be watching you, so, yeah, yeah, yeah, yeah. you know, so yeah, and I think a lot of that narrative around the sort of peak Bad Boy sampling era, you know, I think it gets unfairly criticized as sort of being uncreative and like, you know, essentially just being cover and, not adding much to it.

But, I disagree entirely, and I think that in addition to creating a different song with a different vibe and everything, you know, th those songs did introduce a whole generation of people, to eighties music that, you know, they may not have been alive to have heard, you know, from, you know, let’s say I was born 85, some of these songs came out before I was born.

So, yeah, I think that does get missed sometimes.

[00:27:35] Dan Runcie: Yeah, and I’m in the same boat. I knew Juicy before. I knew the original Juicy Fruit. I knew Mase Bad Boy before I knew Hollywood Swinging, and I could go on and on with all the songs that they were able to help in introduce and connect the dots there. Another thing that I think Bad Boy did at this time that was a continuation of Uptown was how intentional and borderline maniacal Puff was about continuing that image.

So, they had the Can’t Stop Boat Stop documentary that came out a couple years ago. And the artist from one 12, which was the main male R&B group that Puff had signed to the record label at the time, they said that they were styled, dressed and personified to be an image of Puff themselves, to essentially be Puff as R&B singers, which was really interesting.

And then on the more controversial side, which I don’t think would ever fly in the same way today, Faith Evans, who was married to Biggie at the time, she was sent by Puff to go to tanning salons cuz she a light-skinned black woman. They sent her to tanning salons so that her skin can be darker because he wanted to be able to sell her as a certain image that would never fly again the same way today.

But that’s how Puff was. He was so maniacal, even things down to the nail color and things like that for women. He wanted to make sure that people looked a certain way.

[00:29:01] Zack Greenburg: Yeah, and I think what’s, you know, especially interesting when you, kind of zoom back on the 90s and that, that era of Bad Boys, you know, given the level of control he had over, you know, that level of detail, you know, the whole east coast, west coast thing, the whole Bad Boy Death Row thing obviously got way out of control.

and, you know, culminating in, the desert of big and pop and you know, obviously we don’t know exactly who was behind each of those things, but it’s, you know, still kind of debate to this day. But, the fact is that, you know, got kind of wrapped up in this kind of, know, sort of thing, like the fact that Puffy could bring Bad Boy back from that, and kind of like continue to have the same brand, you know, after everything that went down, you know, I think is another testament to like the identity of the brand, right? I mean, you know, cuz I remember in that period of time hip hop was really under fire from, you know, so, you know, like the Tipper Gores of the world and the parental advisories and all that, and there was this narrative of like, oh, this music is dangerous.

And there was a whole period of time, you know, after everything that went down, in the mid to late 90s, like there were questions like, is hip hop? You know, really a viable commercial genre? Are brands really gonna want to be attached to this? you know, because of the violence that happened, you know, really publicly there.

And I think, you know, whether you love him or hate him, like, I think he deserves some credit for pulling things back from the brink. you know, regardless of whatever role he played in getting them, to the brink, but he really did kind of pull things back from the brink and show that hip hop could be this, you know, commercial force.

you know, that would be like a mainstream success sort of thing. And really pretty quickly, after all this went down,

[00:30:39] Dan Runcie: If you go back to winter 96, the height of this beef, you have that infamous vibe cover with Tupac, Dr. Dre Snoop, and Suge Knight. They’re there, the Beef and Bad Boy and, Biggie as well. Were on respective vibe covers as well. If you asked people, okay, five, 10 years from now, which of these two record labels will be in the stronger position, you probably would’ve put your money on Death Row.

To be frank, they had the better artists just from like a roster perspective. With those four, the leadership seemed in many ways quite as strong and there were similarities there as well. You had these two relentless, large and life figures. Granted, Suge and Puff are very different in a lot of ways, but that’s where you would’ve taken things.

But then two years later, it’s a completely different story. Death Row is imploding and bad Boy had the biggest year that any record label has ever had. If you look back at that 1997 to 1998 stretch, and this is after the death of the biggest rapper as well, they end up releasing Biggie’s second album, Life After Death, ironically, 16 days after he passed away.

And then Puff himself becomes this larger than life icon. He releases his own album, Puffy, P uff Daddy, the Family, No Way Out. And they continue to go on this run. And in many ways, as other heads and other figures in hip hop have faded and necessarily taken their own path, he continued to stay on that.

It really is a remarkable journey when you look at each of those steps in it, because I probably would’ve put my money on Death Row if I didn’t know better.

[00:32:21] Zack Greenburg: Yeah, Yeah, I mean, it sure felt that way, right? I mean, but if you kinda, if you compare the leadership, if you compare Puffy to Suge, you know, I think that so much of, you know, the back and forth between Bad Boy and Death Row, you know, it was a case of like, these guys were playing a role, right?

I mean, they were, it is funny in some of my reporting, people say like, both Puffy and Suge, especially Suge, were sort of, it was like they were acting in their own bad gangster movie. And I think the main difference was, you know, Suge really came to believe it and live it in a way, that Diddy, didn’t quite do it you know, as we were saying before, Diddy kind of walked that line.

but Suge just kind of got deeper and deeper into it, and that was kind of who he was, you know, all the time. So, you know, that there’s not really like, kind of like a way to, back out, you know, to kind of come up for air when you, when you’ve kind of like gotten that deep into it like Suge did.

 I think that was the main difference, you know? I mean, I think he became just completely, you know, is like possessed by this image that he created for himself. And he started to live it, you know, all the time and Diddy’s ability to sort of walk the line and step back, you know, I think that’s what ultimately kept Bad Boy in the position that, you know, that stayed and kept him in the position that he continued to be in. 


[00:33:42] Dan Runcie: And everything that went down to that 1995 Source Awards is a perfect example about how they dealt with this whole thing. Suge and Death Row, famously win Best soundtrack for Above the Rim. He goes up, accepts the award, and he makes the infamous line. If you wanna sign with the label, you don’t wanna have your executive producer all on the record, all on the video dancing come to Death Row, and then you see.

Puff is there just looking, not saying anything, but everyone knows who he’s talking about. But then later on the night Puff goes and is on the mic, he doesn’t go necessarily take a shot back at Suge, but he just makes some type of more global statement, Hey, we’re all in this together. I forget Puff’s exact quote, but that’s a perfect example of this, right?

Of knowing that line cuz as we know, puff had a temper. Puff wasn’t afraid to throw down in the moments, right? But he knew that in that stage, in that setting, especially even on his home turf, this was all the West Coast guys coming there because, you know, there was that famous scene of Snoop Dogg standing up being like, East Coast ain’t got no love for Dr. Dre and Snoop. 

That’s my horrible Snoop dog voice there. But Puff was cool, calm, collected during all of that, and as you put it, the difference behind the difference between the two of them is more than puff deciding to be all the video and should not be in, the video. The same way it was everything that you explained it more.

And that is one of the biggest reasons, I think for that difference. And what helped Bad Boys essentially be even stronger, unfortunately. So after Big’s death,

[00:35:21] Zack Greenburg: yeah, totally. And you know, I think with Puff, he ultimately. He had that calm, cool, collected side to him that came out, you know, I think at, helpful points, but he was ultimately about, you know, protecting the bag, right? Like Diddy is a business, he is the business. And he, knows that he has to kind of keep that in mind.

And I think, you know, Suge on the other hand just kind of like got too deep in his own narrative and couldn’t kind of like poke his head up over the clouds and see the view from, you know, 35,000 feet or whatever. So, I think Diddy’s business sense, you know, I think ultimately helped keep him, keep him, you know, just above the fray.

So, still super remarkable when you look at it. He threw that first white party in 1998. That was really, that was what, like a year, a year after Biggie was killed. And, you know, just to give you an idea of the kind of stuff that was going down. I mean, he bought this house in East Hampton, and he decided that he was gonna throw the most exclusive party people just to give the background.

I did some reporting on this too, but like, it apparently if you got invited to the white party and Puffy’s White party, you could not get in If you wore like a cream suit, they’d throw you out. If you had, like a blue stripe on your white shirt, they would throw you out.

So you had like grown men running home to get like an all white proper shirt to go to these parties. And you know, like pretty quickly you had Martha Stewart and Howard Stern and Donna Koran and like, Donald Trump used to go to these parties, you know, with his daughter everything. So, it was kind of like a who’s who of like a certain type of celebrity in the late 90s.

And to go from, you know, from the depths of the East coast, West coast thing to that, in like a year. I think it just shows how Puffy’s able to kind of flip things around and that’s what he was able to do with Bad Boy. He pivoted the whole narrative and suddenly it was about Puff Daddy, the family.

It was about, you know, Godzilla soundtrack and, you know, doing the thing with an orchestra and Jimmy Page and whatever. And, you know, singing, he’s able to like recreate himself and also these brands like Bad Boy that’s created in his image. you know, like in a remarkably quick timeframe, I think.

[00:37:38] Dan Runcie: And to share some numbers on this era. This is peak Bad Boy. I would say this whole 97 to 1999 stretch. 1999, they sold 130 million worth of records. And for some context there, that was more than Madonna’s Maverick label had that year. And this was, or Madonna, during that whole Ray of Light era, if I’m remembering the timeline, and Beautiful Stranger, if I remember the timeline correctly and more than Def Jam had at its peak that year, and this was, we did the Def Jam pod recently.

This was around the same time that Lyor was trying to get X and Jay-Z to release those albums in the same year, and Bad Boy was still doing its thing then they’re Puff Daddy and the Family Tour. They went on their own arena tour, they made 15 million that year, and Puff was starting to extend himself in the same way that we saw other moguls do the same.

We talked in the Roc-A-Fella episode about, this was the time that Dame Dash had started to have different partnerships in film and district and sports and things like that. We saw Master P as well in the late 90s get his hand involved with a number of things. And one of the things that stuck out from this era is that Sean, is that, did he actually made a partnership with Johnny Cochran at the time, who was his attorney during all of the drama that he had in the late 90s after that nightclub shooting. And they started a management business that was gonna be focused on NBA players. And this just gives you an idea of all of the things that he was interested at the time.

So it really is remarkable. And a lot of it came because Diddy himself was putting himself out there. He became the brand, it was him putting it on, and he really became the most successful artist on this label. But around this time, if you start talking to some of the other artists on the label, they start to get a bit frustrated because they feel it’s no longer about their development.

It is now about Puff building and doing everything for himself.

[00:39:36] Zack Greenburg: Yeah, and I think that’s when you know, he really starts to have all these brand extensions and, you know, you can see there’s actually, I think the first Forbes cover on a hip hop artist was Puffy in 1999. And, it was a celebrity issue. And they had, Puffy and Jerry Seinfeld on the cover together, which always cracks me up.

But, you know, Seinfeld’s wearing this suit and Puffy’s got this like Sean John denim t-shirt on. you know, just like a walking advertisement on the front of this magazine, which is just brilliant. And, you know, so he is got that going. He’s like opening restaurants, you know, and like really kind of like realizing that, he could be not only the sort of the straw that stirs the drink and like the producer and whoever behind the scenes, but also the, you know, the main artist.

And you know, I can imagine that being another artist on Bad Boy at this point, could start to get a little frustrating.

[00:40:28] Dan Runcie: Right. And I think he had a quote around the time he wanted to be David Geffen. He wanted to be bigger than David Geffen. And of course this was Pete Geffen making moves with Dreamworks and everything else. Still being, in many ways, music’s prominent mogul. That was due his thing there. And this was around the same time that we have another quote from, Andre Harrell.

And I remember if you mentioned earlier, or if I mentioned earlier, there were some other quotes at the time that were less favorable than Diddy, than the ones that Harrell ended up having later. This was one of them. He said, and this was in a New York Times 1999 interview. He, Puff, gotta separate the young man thing from the business thing.

If there’s an incident where the situation is going in a way that he feels slighted or disrespected, the only way for him to handle it is as if he was a 45 year old IBM, CEO, which is a very interesting way. But he’s essentially saying, Hey, you gotta change your act based on where you’re going and where things are.

And this is, that trending the line that we’re talking about that I think that Diddy was eventually able to get to. But there was still some question marks about that and the trajectory in 1999. But to some extent, I think that kind of played to as factor. There was something about, especially some of those celebrities you mentioned, these are some more buttoned up, you know, white celebrities that never really did much on a, anything that was risky.

So someone that has the image of Puff at that time, it’s like, Ooh, I’m doing this risky thing. It’s almost like the person in high school that wants to date the Bad Boy literally called his label bad voice. So they’re leading into that whole persona, and I think it worked a bit to his advantage there as well.

[00:42:07] Zack Greenburg: Yeah, totally. And you know, another thing people talk about, you know, I think that this time, and a lot of times I think there’s a lot of jealousy going around and, you know, Puffy does this, puffy does that. But, know, one of the things that I, that I’ve always heard is that, Like, yeah, he’s the last one at the club and you know, he’s always out and, doing whatever, but he’s also the, first one in, like, he outworks everybody and you know, he’s somehow manages on, you know, like a couple hours of sleep at night or something.

I mean, this is another thing you sometimes hear about fantastically successful people. I hear about this, about like Richard Branson and other people too, that they just can operate on four hours of sleep or something like that. And man, you know, I mean, if you think about it, if you have that much confidence and you’re that brilliant, and then also you get an extra four hours a day, you know, you get another, was it, 28 hours a week, you get like an extra day every week basically to just like do shit.

that’s pretty hard to, contend with. I mean, like an extra day, like two extra waking days, to get things done. I mean, that, that’s a pretty big advantage.

[00:43:13] Dan Runcie: That was a whole 90s mentality from, overall, from people that were successful. Now that I’m thinking about it, cuz of course Richard Branson, that the 90s was a transformational decade for him. You are Bill Clinton, especially when he was president, talk about getting four or five hours of sleep at night, still being able to operate and do his thing.

Even folks like Madeline Albright, who worked for him and in his cabinet were doing the same thing. And even someone like Kobe Bryant, there’s that memorable. A piece of the Redeem Team documentary that came out on Netflix last year, where the younger guys at the time, LeBron, Bosh, Wade, were all going out to the club.

Were all gonna go out for the night because that Olympics was in Beijing and they’re coming back from the club and Kobe’s on his way to the gym in the morning. And then Kobe spoke about this himself as well. He is like, no, I’m gonna do another practice to wake up earlier than everyone else. So you think about how this compounds over time, and that’s what you’re saying about how that essentially gives you two, three extra days a week.

You do that time and time again, and just how much better you get. Granted the fact that those people can still do that while not requiring that much sleep. I know. I mean, I couldn’t do that myself. I need those hours of sleep, but I commend those people that can.

[00:44:25] Zack Greenburg: Yeah. I mean, and who knows, you know, from a health perspective, how it affects you, you know, sort of like later in life and whatever. And, you know, do you lose more years of your life on the tail end because you didn’t sleep more earlier? I mean, I guess we’ll never really know, and it’s hard to kind of pull out the factors and really test that.

 But in any case, you know, it does give a decided advantage, at least in the, present tense. And, he really kind of like worked with that. but you know, I mean, and then just when you thought that he was kind of out of the woods, with the specter of violence, you know, again, 1999, there’s the whole thing in the club, a gun goes off, you know, there’s this whole like, situation, Diddy and Shine are in the club. There’s this dispute, whatever, and you know, who knows what really happened, but at the end of it, Shine went off to go to jail. And, you know, and Diddy ended up, you know, without really any kind of anything other than like, a little bit of reputational hit.

So, I think that, you know, he continued to walk that line, right? And there were just these instances kept popping up. But once again, he always managed to sort of, you know, avoid any really serious repercussions and then, you know, go on to some even bigger and better commercial thing, shortly thereafter, you know, which he did eventually with Ciroc and, what have you.

But, you know, it didn’t really seem to hurt anything with Bad Boy. Although I think around that time, you know, his career as a solo artist started faltering a little bit to be sure

[00:45:42] Dan Runcie: And I think this is a good time to talk about the proverbial Bad Boy curse that’s been discussed. There are a number of artists that have had their issues with Bad Boys, specifically with Diddy in terms of whether they feel like they were fairly compensated for things. And it’s artists like Faith Evans 112, Mark Curry, and the Locks as well as most recently as a couple years ago, Mase famously people that have publicly claimed to try to get what’s theirs called out Diddy for not doing certain things.

And then on the flip side, you have people that surrounded themselves with Diddy, and Diddy was the one that came out, scott free, and they were the ones that ended up in challenges and some of that Diddy benefited from by associating himself with them, but they didn’t necessarily work outta that same way.

You of course mentioned Shine, who, his career never really took off after he had that brief moment where that Bad Boy song came out. I think that was in 2000. They had sampled that, the Barrington Levee reggae song and then had him on that. But you had a few instances like that. I look back on one of my favorite songs from The Bad Boy era.

let’s Get It with G. Dep and Black Rob. And the sad part about that song is that you have G. Dep, the first person that was. Or essentially his lead single, he’s saying that he’s saying, or he did special delivery as well. G. Dep eventually ended up being locked up for a murder that he had done in the 90s, but then it had some run-ins after that Black Rob unfortunately passed away a few years ago, and I don’t think was ever really able to capture that momentum after Whoa. And a few of the other songs he had with Bad Boy had come out. And then of course you had Diddy who, you know, is still thriving doing his thing.

And I think that’s true as well. You look at an artist like Lone who l kind of had his moment where they were trying to make lone really be a thing, especially with the, I need a girl, part one and part two, but then Loon as well, ends up getting locked up. I think there was a heroin charge or something like that.

So all of these folks that were around Diddy in some way ended up having their challenges. Not all of them, but some of them.

[00:47:50] Zack Greenburg: For sure. And I think, you know, probably around this time, you know, the sort of like the turn of the millennium was, you know, the moment, when did he kind of realize that he had to, he did have to start figuring out his next step. And if it wasn’t gonna be him, as an artist, you know, and it wasn’t gonna be somebody else on his roster, it was gonna have to be something else.

 And so I think this is sort of like when you think about the Bad Boy era, you know, I don’t know, I think about it as sort of like early 90s to late to, you know, to really the end of the decade. And although, you know, of course it went on and it continues to stay at different, you know, sort of capacities.

It’s like that was sort of the prime era. And, I think once the fortunes of the label became too closely intertwined with Diddy’s as a solo artist, then when he stopped being such a big deal as a solo artist, the prospects of the of Bad Boy itself were a little bit more limited.

[00:48:45] Dan Runcie: Agreed. Question for you. Do you think that, well, lemme take a step back. In the Cash Money episode that we talked about not just the disputes people have had with Birdman and Slim over the years, over disputes, but also the notorious reputation that they’ve built up. Do you feel like the reputation with Puff is similar in that way?

And if it’s different, why do you think so?

[00:49:09] Zack Greenburg: So you mean Puff like the Cash Money sort of similarly having trouble paying people?

[00:49:13] Dan Runcie: Yeah, Yeah, and whether that reputation has stuck with Puff the same way that it’s clearly stuck with Bert and Slim.

[00:49:21] Zack Greenburg: I think they both have, you know, or rather the three of them, I think it does follow them around, but in different ways. I mean, I think, I think with cash money, there’s some element of it that’s like, well, you know, I think their response to a lot of it is this stuff began when, you know, the things weren’t properly papered up and, you know, nobody really knew how these things worked and blah, blah, blah.

And you know, you can sort of agree with that or not, right? Or maybe you could say it is to some extent your responsibility to make sure things are paid up, you know, once you become that successful. but, you know, I think that Puff was sort of like, you know, Bad Boy was, done through Clive through real estate.

It was done through a major label, sort of from the beginning. And, you know, I think you could argue actually that that’s why Cash Money was ultimately worth more, like, was like a bigger source of the Williams Brothers wealth than Bad Boy ever was, for Diddy. And he had to go, you know, do these other things.

 But you know, like it wasn’t as though there were no lawyers involved. It wasn’t as though there wasn’t some big record label apparatus. There absolutely was. And you know, so I, think that excuse sort of like, doesn’t fly quite as much. it’s probably not leveled quite as much with him either, but, you know, but it’s definitely there and, it’s sort of like, it’s hard to look past it in some regards.

[00:50:41] Dan Runcie: Yeah. I think that one of the reasons why I think the public image of it is different is because of the businesses that the two are involved in. Bird man’s a music man almost in the same way that Clive Davis is a music man. That’s what we know him as even in the conversation you had shared last time where you were doing this extensive feature profile with them on Forbes and you were gonna have another follow-up conversation with him that night, and he’s like, no, no.

Bird Man’s still in the studio. He’s doing his thing like that’s what he wants to do versus Puff has his interest in all these other areas, beverages, spirits, sports, entertainment, now with Revolt or Sean John, or whatever it is. So there’s so many more things we know him as, or he’s running the New York City marathon, he’s trying to launch this thing, and all of those things can broaden your image of him.

So if you hear a complaint about the one particular aspect of this business, that’s one area of what he’s doing, as opposed to us knowing Bird and Slim as. The owners of this record label, and now there’s a dispute with the one thing that we know them for.

[00:51:49] Zack Greenburg: Yeah. Okay. I see what you mean. So it’s sort of like, in a way it’s less central like the music is less central to his identity, therefore we hear less about the disputes because we just hear less about the music side overall. 

[00:52:01] Dan Runcie: Right. 

[00:52:02] Zack Greenburg: Yeah, that makes a lot of sense. I mean, and then, when you look at what happened to Bad Boy, you know, even just from a corporate perspective, it was a 2005, he sold 50% of it to Warner for 30 million bucks, something like that.

So, obviously that, means, you know, by those numbers it was worth 60 million. At the time there was probably just the recorded music side and there was publishing as well, which is separate. I think you did some other publishing deals too, but you know, that number in 2005, I mean, I’m sure that’s lower than.

Cash money was valued at in 2005. But, you know, he just kind of made the decision to pull some money off the table, right? And I think that says some, something about his priorities too, that he wasn’t that focused on the music side of things. So, you know, like, let’s make this deal and then move on, to the next thing.

And I think a couple years after that was when he launched Ciroc or, you know, came on with Ciroc and launched his Ciroc campaign presence, whatever you wanna call it. you know, partnership thing. So, I think ultimately for Bad Boy, you know, I think it had a peak that was as high as really, you know, any label, in hip hop did.

But its fortunes became so wrapped up with Puffy that once, once he moved away from music, it’s like, how are you ever really gonna come back from that?

[00:53:15] Dan Runcie: Right. It really wasn’t a business it was a business, but almost in the same way that a lot of people that are creators now and trying to do things, there’s this ongoing discussion or debate they have about whether are you trying to build a business with a roster around you, or is this more so a soul entity?

And I think Bad Boy definitely saw both of those things, but you normally seen in the flip side where you start with the lead person being known as the thing, and then they add the roster around them. But Bad Boy was kind of the opposite, where you had this roster and then it becomes the lead person becoming more known for the thing.

[00:53:48] Zack Greenburg: And I think it moved away from that assembly line idea, you know, the Motown thing, the Coachella thing, whatever, you know, you’re gonna, buy the tickets for, you know, who’s there. It just became all about Puff and, you know, I think in a way he realized it was more lucrative that way, right? N o matter how involved he was in however many different pro projects as sort of the, the Berry Gordy, he could make more, you know, for himself being Puff. And in a way, when you look at Ciroc, it’s like, you know, it’s the same thing, right? Like he’s selling the Art of celebration.

 He’s selling his brand of success. He just doesn’t have to sign other artists to it, you know? So I see has Ciroc Boys, you know, that’s, I mean, it is almost like a record label to some extent, you know, if you like an extension of, Bad Boy. If you think about, you know, the different artists who are kind of like involved on some level, you know, over the years with that brand, it just, you don’t have to get involved in like publishing and, you know, licensing and mechanical royalties and all of that fun stuff.

[00:54:50] Dan Runcie: Right. And I think with that it’s a good chance to talk about some of these categories we have here. So what do you think is the best signing that Bad Boy did?

[00:54:59] Zack Greenburg: I think a hundred percent, you gotta go with Biggie, no doubt. I mean, you know, if you’re calling the signing $500,000 to get him over from uptown, you know, plus whatever they ended up paying him. I mean, you think about the success of Life after Death and all the other albums and, you know, the albums that, were sort of in the hopper after he died.

I mean, I think hard to top that.

[00:55:19] Dan Runcie: Agreed. Yeah, No debates there. That was the same one. What do you think is the best business move to come from Bad Boy?

[00:55:26] Zack Greenburg: I would, I would argue that, I would argue Sean John because, you know, in creating the Bad Boy image, that was, you know, really bankrolled like all those videos, obviously Bankrolled by Arista, bankrolled by, you know, the, parent company, you know, Puffy created this aura around himself, which was very fashion oriented.

And then he was able to parlay that into creating, you know, an actual fashion brand that he owned, or at least, you know, partially owned and himself, which then generated hundreds of billions of dollars. And then he sold and got, you know, whatever it was, a hundred million dollars and he bought it back.

but anyway, he did really well for himself. I think with the help of this shine that was kind of like given or enabled at least, by a Bad Boy.

[00:56:13] Dan Runcie: Yeah, I think that’s a good one. The other thing that I wanna give some love to, that we haven’t talked about much yet, but was the Bad Boy Street team and how they went about promoting and pushing their records all over the major cities. A lot of people may think that Bad Boy invented to the street team.

I think I still do give loud of records credit for that, but Bad Boy did take things to another level, and this goes back to Puff and his strength as a promoter. This is what Club promoters do. This is how you push and get the word out there. So he’s able to replicate himself. He’s able to empower the people to feel like they’re part of Bad Boy himself and making sure that they’re styled in the same way, to be able to help sell that same image that Puff wants to sell himself.

And you saw him replicate this as well with Ciroc Boys and things like that. And shout out to Sean Perez, who worked with Puff at Bad Boy and on Ciroc on this same strategy.

[00:57:07] Zack Greenburg: Yeah. Although, you know, it was a great one, and a great strategy, but it didn’t always work. What’s the line? I felt like Bad Boys Street team, I couldn’t work. the locks.


[00:57:19] Dan Runcie: Yeah. Usually worked. But yeah, they just needed to see the vision as they said. what’s the best dark horse move? You have a good one for this.

[00:57:27] Zack Greenburg: Yeah. Yeah, yeah. Okay. maybe a little controversial. I don’t know. I’m gonna go shine. Because if Paul hadn’t signed Shine, I mean, I don’t know, you know, I’m not a lawyer or anything, but, all I know is that something went down in that club and, Sean ended up doing, you know, like a decade and, Puff, you know, got away without any trouble.

So, I think that worked out pretty well. But actually I think they’re back friends also, Shine, you know, like converted to Judaism, moved to Israel, then he’s like back in Belize where I think he was born and now he’s like a member of parliament or something, and Puff has helped him with his campaign and there, so there’s like pictures of them together and they’ve managed to patch things up.

So, you know, I think that speaks to Puffy’s gratitude for whatever, you know, whatever went on in the late 90s there, 

[00:58:10] Dan Runcie: so signing a fall, man.

[00:58:12] Zack Greenburg: Yeah. Well, well, whatever you wanna call it. I don’t know. I don’t know, and people forget that Shine was supposed to be the next Biggie.

Like you know, he was sort of like the heir apparent 

[00:58:21] Dan Runcie: He had the voice, He had the vibe. you hear Bad Boys, that, I know I mentioned it earlier, but you hear that Bad Boy song in Beson Levy, you’re like, oh, he has it. It’s almost in that same way where there’s people that have that grit that reminds you of that, like New York Grit sound, whether it’s a, Chuck D or even when, I know people may laugh at this, but when Ja Rule first came out and they were hearing him on mixtapes, they thought he had that same sound too, and Shine had it.

[00:58:45] Zack Greenburg: yeah, yeah. Absolutely mean DMX had that edge. So, yeah, I wondered what would’ve happened with Shine, you know, ultimately if things had kind of gone differently there. but you know, and I think Puff has expressed this, but he’s kind of, he feels bad about the way things went down and he, he feels like, you know, that Shine ultimately got the short end of the stick and, you know, but they seem to have, you know, gotten over it at like even more than some artists have gotten over whatever, you know, royalty situation, that they don’t agree with. So, you know, there’s a dark horse candidate

[00:59:14] Dan Runcie: Yeah, that’s a good one. The one I have is the original hip hop artist partnering on a fast food release, and that is of course the Big Mac. We go back to mid 90s, I think it was 93 or 94. They have the Big Mac meal, and that was part of the push to have Biggie be more present. And this is where you’re already seeing how Puff is thinking about how to have his artist be part of that lifestyle.

What are you trying to sell, what are you trying to integrate with? And then of course, we saw things blow up 25 years later with all of the meals, with the Travis Scott meal and the J Balvin deal and all of the things that McDonald’s had done, especially in the beginning of the pandemic, you saw Burger King and others fall in line.

And these have always happened in waves, but I always point back to that one as that was the original one. I’m necessarily know about the sales numbers, but if anything it sticks out more so as. That mentality.

[01:00:12] Zack Greenburg: a really good I, I like Uh, certainly fits with everything that, that puff has been about, um, forward too. So 

[01:00:19] Dan Runcie: Yeah. 

My missed opportunity for bad. Boy, we’ve alluded to this several times, but not being able to make things work to some degree. In the two thousands. I think that a lot of people talk about the demise of New York hip hop and how strong New York hip hop was in the 90s and what happened in the two thousands.

And I think you still had strong artists in the two thousands. You clearly had the 50 cent beef. You clearly had Daisy and Nas. These are all things that happened in the two thousands and heat up, but there really was an opportunity to be able to see some of that continue. We saw that brief moment, I think it was in 2006, where Diddy releases press play.

They signed Cassie and you start to see a little bit of this comeback. He then has another one in 2011, I believe, where he releases that song, I’m Coming Home and that becomes


[01:01:16] Zack Greenburg: that was a really fun song. I like that song a lot 

[01:01:18] Dan Runcie: Yeah, and that was a big hit. That was a big hit. And it’s like, okay, you know, Diddy’s over 40. Now he’s still able to command himself on the radio, And granted, I don’t think that Diddy necessarily tried to position himself as the best rapper himself like he wasn’t Jay-Z necessarily. Where, okay, it makes sense for you to continue to be the brand, but if you know that you’re not necessarily going to be known as that, how do you find ways to continue that?

And I know that they tried to sign artists, and I know that’s several of the artists I mentioned had had their struggles. But where was the opportunity to have a bit more time to nurture these artists and not just nurture ’em from a talent perspective? Cause I think many of them were clearly talented, even on the R&B side.

I think about artists like Mario Winans and folks like that. But how do you find the way to really cultivate and build this as a unit the same way that others in New York were starting to do at the time? It’s almost like when Bad Boys started to decline. You saw the rise of Roc-A-Fella, you saw the rise of Dipset, you saw the rise of all these other groups in New York that were doing their thing.

[01:02:16] Zack Greenburg: Yeah, I think that’s a great one for missed opportunity. I mean, I was gonna say the locks, you know, to go back to that line, Bad Boy Street team couldn’t work the locks. But, you know, I love the locks. They were great and, you know, like, ah, how did you, you mess that one up? But, you know, if you kind of look at what the locks were about, and what Bad Boy had kind of evolved to be about, you know, this was sort of like post shiny suit era.

Bad Boy had gotten away a little bit from what it was. In, you know, the early to mid 90s and it was like, maybe got a little too glitzy and so it was sort of at odds with where hip hop was at the time. And, you know, this was around when 50 cent was becoming really big and kind of taking things over.

Things had gotten sort of like a little more aggressive again and, you know, like, a little more of that edge. But, you know, Puff had kind of like moved even beyond that to the point where, you know, I don’t know that puffy in that era could have even been an artist on his own label and in the early to mid 90s, right? And whereas I think the Locks would’ve been a perfect fit in the early to mid 90s. It was just a little bit of an odd, you know, combination by that point, with what Bad Boy had kind of, you know, evolved into. so in a funny way, I would almost say like, they should have done a trade, they should have traded the locks for Camron or for Dipset.

You know, I mean, I feel like Dipset, there’s the Harlem connection, you know, like Come home with Me, had a little bit more of that Bad Boy kind of vibe to 

[01:03:52] Dan Runcie: definitely. 

[01:03:54] Zack Greenburg: yeah, yeah, 

[01:03:55] Dan Runcie: Oh boy. Especially with the samples as well 

[01:03:57] Zack Greenburg: Samples and, you know, whereas like the locks I think would’ve fit more in with what, Roc-A-Fella’s doing at the time, you know, in state property and all that stuff.

So, you know, like little fantasy baseball trade. I know it doesn’t work like that in music, but, 

[01:04:12] Dan Runcie: I wish it did though. I wish it did. 

[01:04:15] Zack Greenburg: That could have been really fun, right? And I think we said last time that Cameron and D ipset said were sort of like a bit of a missed opportunity for Roc-A-Fella and, you know, I wonder if things had been flipped, if it would’ve turned out differently for both those acts.

[01:04:28] Dan Runcie: Great example. I think that Bad Boy not being able to work the locks it in many ways reminds me of the The oklahoma City Thunder, not being able to figure out why they should keep James Harden. And then they trade James Harden for Kevin Martin and then James Harden goes on to beat this MVP candidate and it’s like, oh shit, we had that.

Well, I mean, you knew you had something, the guy was sixth man of the year. He played meaningful minutes in the finals, in 2012 when they played the heat at the time. But yeah, that’s exactly what this was. And then he goes and does his own thing and it’s like, oh shit. That’s what we had. And you saw the same with Jada Kiss to some extent.

Oh one, he releases Kiss the Game Goodbye and we gonna make it is one of the best hip hop tracks from that era. And it’s like, oh, we had this all along granted. And I don’t think that the locks, I mean the locks still were on plenty of Grammy award-winning singles and big splashy hits like the Honey Remix and stuff like that when they’re on Bad Boy.

But you were able to really see them get and. Live their own life and breathe in away. So, yeah. Oh man. The locks for Camron 

[01:05:34] Zack Greenburg: The locks were Dipset to make it even. Yeah. 

[01:05:37] Dan Runcie: That would’ve made that whole versus battle something completely different.

[01:05:41] Zack Greenburg: Yeah, yeah. Exactly. So, I don’t know, maybe it’s not too late. maybe they can work that out. you call Puff. I’ll call Jay. How about that?

[01:05:49] Dan Runcie: I know. Let’s do that. Let’s do that

[01:05:50] Zack Greenburg: Or you wanna flip it? I don’t know.

[01:05:54] Dan Runcie: Well, the one they keep talking about now is, well by they, not the actual people a verses, but Puff and, Jermaine Dupri himself, they keep talking about that one, trying to do a so-so death versus, Bad Boy versus, but we’ll see if that one ever happens. I feel like that’s kind of Puff doing the hype machine and just staying in the conversation. 

[01:06:12] Zack Greenburg: You know, I don’t know. I think it would be more fun to see like, if you could get, you know, obviously you couldn’t do Bad Boy Death Row with, Puff and Suge, but you could do what if you did it with like, Dre, you know, and Snoop, you know, and then you had Puff and somebody else.

I don’t know, but I don’t think they would do it. It’s like maybe a time that, you know, we don’t wanna revisit it anymore, but yeah, we do hear, 

[01:06:32] Dan Runcie: Yeah. but no, there’s definitely something there. But yeah, before we wrap things up, though, I know the answer to this one, but who do we think want the most out of Bad Boy?

[01:06:41] Zack Greenburg: Oh, yeah. Puff, I

[01:06:42] Dan Runcie: Yeah, not even a question. I mean, maybe to his fault to some degree, but it’s one of these things where I don’t think it would’ve reached the same heights it did, especially in the late 90s if he wasn’t front and center.

But that was more of a short term money grab, in my opinion, just given the nature of it and not being able to really build a strong business. That said, he was able to build strong businesses off the back of what he did, and we all know how music is a platform to be able to build other businesses, just so shout out to him for doing that.

But there was a world where you could have done all these things by having 

the right people around you.

[01:07:16] Zack Greenburg: For sure. And you could also say, of course, like with Biggie, you know, biggie wasn’t really breaking on Uptown, but he did break on Bad Boy because Puff knew how to market him. you know, certainly it all worked out very well for, Clive Davis. you know, I think that kept him relevant in a way that, you know, would not have been possible otherwise, perhaps for like an extra, you know, couple decades, in certain spheres anyway.

 And, you know, still considered one of the great, record executives of all time. And I think, you know, Puff. Puff really helped burnish that legacy. So, you know, I mean, there were other people who won, but I think Puff, certainly won the most

[01:07:52] Dan Runcie: Without a doubt. anything else before we wrap things up on Bad boy?

[01:07:56] Zack Greenburg: Can’t Stop Won’t stop, right? What’s he gonna do next? I don’t know, you know, I mean, just when you think that you know, Bad Boy is like in, mostly in the rear view and it’s, you know, legacy nostalgia thing, you know, he goes out and he does a Bad Boy reunion tour and he manages to pull in all these great people.

I mean, I remember going to see him at the Barclays Center when they did that whole thing. And, you know, in addition to, to pulling, you know, most of that roster together, he just brought Jay-Z out, like surprise, you know, here you go. So, he has that ability to just pull all kinds of rabbits outta hats.

you know, and, that could be Bad Boy related or not.

[01:08:32] Dan Runcie: That show was a lot of fun. I saw it here. they had it at Oracle, Oakland. It was a lot of fun, waiting to see if they’re gonna do a movie. You think Puff would sign off on that?

[01:08:41] Zack Greenburg: Ooh. Yeah. You know, I mean, I think it depends, how it aligns with everything else, you know, is there like a Ciroc placement that could be had? you know, that kind of thing. I could see it. I could see it.

[01:08:52] Dan Runcie: I could see it too. I know that there’s this fine line where some of these movies, especially if the main person involved is a little bit too attached to the project, then there’s certain things that are gonna be sanitized over and even a conversation like you and I had, a lot of the things that we discussed may not even make it there.

And I know that there’s a fine line with these things. I think that’s Straight Outta Compton. Navigated that pretty well. And I think that’s still my favorite hip hop biopic that we’ve seen done so far. Granted, people still felt that they glossed over Dr. Dre’s controversies with women. And to be honest, I think that differ that movie would be received differently and maybe even have some different reviews, especially if it came out in a Post Me Too era.

But it’ll be interesting to see if they do something like that. I mean, Puff is always in the business of maximizing things. And I’d had Tarik Brooks, who’s now president of Combs Global on the podcast, and it sounds like, wow, he probably wouldn’t wanna sell any of his music, rights that he may own in the same way they could be interested in further multimedia.

[01:09:56] Zack Greenburg: right. I mean, there was that biggie biopic that, you know, that may have already kind of gobbled up some of the, the part of the story that, you know, would, be involved in a Bad Boy.

[01:10:05] Dan Runcie: Oh, yeah. Notorious, right? That came out in like 09′ or so. 

[01:10:09] Zack Greenburg: Yeah, yeah, gosh, I can’t believe it’s that long ago already, but, you never know. It’s already been, gosh, almost 15 years,

[01:10:15] Dan Runcie: Yeah. It’s like how many Whitney Houston Biopics have we had, right? I think there was at least two of ’em. And then you had this bigger one come out last year, so you never know.

[01:10:23] Zack Greenburg: Yeah. Yeah. Yeah. Sponsored by Ciroc.

[01:10:26] Dan Runcie: Sponsored by Ciroc that this podcast is not,

No, just to clarify. No free ads here, but 


[01:10:34] Zack Greenburg: Yeah,

[01:10:36] Dan Runcie: But Zach, thanks for joining. Pleasure as always, man.

[01:10:39] Zack Greenburg: As always, Dan, thanks for having me.

Dan Runcie

Dan Runcie

Founder of Trapital

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