30 years of Bad Boy Entertainment (with Zack Greenburg)

We can’t tell the story of hip-hop without mentioning Diddy and the record label he started. Bad Boy took off in 1993 after Puff was fired from Uptown Records. He brought TheNotorious B.I.G. with him from Uptown Record, and signed a 50-50 deal with Clive Davis’s Arista Records, and it was off to the races.

Bad Boy survived the tragic fallout of the East Coast vs. West Coast rivalry, and reached even bigger heights after Biggie’s death. Puff began to rise as a solo artist, but did the rest of the artists suffer as a result?

Friend of the pod, Zack O’Malley Greenburg, joins me on this episode to cover 30 years of Bad Boy Entertainment. Here’s what we hit on:

0:35 Sean Combs come-up story

5:16 Diddy breaks in with Uptown Records

8:22 Starting Bad Boy Records

14:11 What sets Diddy apart

21:04 How Diddy controlled the narrative

23:58 Bad Boy’s formula for success 

29:00 East Coast vs. West Coast rivalry

30:39 Bad Boy’s historic 1997-98 run

45:42 Bad Boy curse?

48:44 Diddy’s reputation compared to Cash Money

54:50 Best signing? 

55:19 Best business move?

57:19 Best dark horse move?

1:00:19 Missed opportunity?

1:08:52 Possibility of biopic?

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Host: Dan Runcie, @RuncieDan, trapital.co

Guests: Zack O’Malley Greenburg, @zogblog

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TRANSCRIPT

[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.

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[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 basic