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Inside ‘Caresha Please,’ Yung Miami’s Chaotic Podcast We Can’t Stop Watching
Caresha barely blinks. She’s an endearing presence with a steady, somehow both warm and unnerving gaze. It’s like she wants it to be known that she’s here. That she’s listening. But that steadiness seems to be a tool to mask her nerves. It’s been almost a year since she launched Caresha Please and she’s reflecting on its success, and the energy she brings. “I be nervous as fuck,” she whispers in earnest about interviewing her guests. “I’m a shy speaker, I got a strong accent. I talk different. So when I do it, I be so nervous… But now I’m getting more comfortable and having fun with it.” Caresha, the host, officially launched Caresha Please in 2022 to much discourse and buzz, as the lord intended. We get into it, and it’s impossible to talk about the show she now famously fronts without speaking of Diddy. The rap mogul and businessman, who recently added Love to his list of tags, is part owner of DeLeón tequila (sponsor of the show), and owner of Revolt network, home of both Caresha’s podcast and Respectfully Justin, a podcast with Diddy’s son Justin Dior Combs and IG meme curator and “Demon Time” founder Justin Laboy—the self-proclaimed “toxic duo” that hasn’t released new episodes since August of 2021. But during her and JT’s appearance on the latter, the idea of dipping into media was planted.
“Diddy had came and then after the show, [he] was like, ‘I like the way you was answering them questions,’ and that hit me off guard. I was like, ‘Huh?’ [and] he was like, ‘You got such a great strong personality; I want to link up with you or whatever.’ So I had ended up linking up with him at Miami at his house, and he was like, ‘You ever thought about doing a podcast?’ And I was like, ‘No,’” she says with a straight face. “[But] he was like, ‘I think you would do good. I think you’d be a great host.’” Although she was hesitant at first, Caresha’s team echoed the sentiment, encouraged the venture, and eventually convinced her to take the leap.
“I don’t feel like you should mix friendships and romantic relationships into business because it never works out. It’s too personal.”
So, naturally, for the inaugural episode of the podcast, which they ultimately launched in June of 2022, the two sat face-to-face as Caresha, the lover, gave viewers a taste of the deliciously daring energy she’d subsequently bring to the ongoing series. Similar to shows like Drink Champs or the newly launched The Wine Down With Mary J. Blige—on which Caresha and Taraji P. Henson served as the R&B legend’s first guests—alcohol acts as a guest of honor on Caresha Please. She recalls being the most drunk when interviewing Diddy, G Herbo and Latto, in that order. She was so drunk on the first taping with Diddy that it required a whole reshoot, resulting in what we ended up feasting our eyes on. She laughs at the memory now, saying, “I’ma tell you the truth… Say today is Sunday; we had did Caresha Please on Saturday. I got so drunk that we had to do it again on Sunday… I had to scratch it.”
Among the many spotlights from that episode was the question of how they individually handle romantic partnerships; at the time, Caresha said, “We ain’t done until I say we done.” Nine months later, when I ask if they’re done, she says, “I will say this. I will say that I am single. That’s my friend. He gon’ always be my friend… we were friends first. But yeah.” Period.
An hour or so after our chat, she went on Twitter to reflectively punctuate that thought and expand on her learnings from the entanglement, writing, “I’m not sharing my next [ni***a]!”
The two spawned dating rumors in 2021 and developed a kindred friendship since, fueled by ambition and love. They never publicly defined their romantic relationship, and media pundit DJ Akademiks commented on that decision, unprompted. In December, when Diddy formally announced the birth of his family’s latest addition (he and Dana Tran’s daughter Love Sean Combs), the podcaster referredto Caresha as a “side bitch.” Dear friends like rapper JT and makeup artist turned rapper Saucy Santana—who she credits as the reason the show bears its name—swiftly came to her defense, writing “With them, it’s a good situation…. They’re a power couple.”
Reflectively, when asked about conjoining the intimate and professional, Caresha advises against it: “I don’t feel like you should mix friendships and romantic relationships into business because it never works out. It’s too personal.”
She speaks on that particular exchange with DJ Akademiks in December, as well as the influence that media personalities like him hold, and puts it plainly: “They some bitch ass [n****s].”
The controversial male hip-hop media personality is prevalent in the space Caresha stands in. They’re the norm rather than the exception, and some of its most influential figures have built large followings because of their dangerous rhetoric and general affectation of superiority over women rather than in spite of it. Over the last few years, in tandem with their rise, several of them—including Joe Budden, DJ Akademiks, Adam22 and others—have been accused of alleged sexual assault or harassment and have had both their content and personal integrities questioned by members of the media who they now share prime real estate with. In the days following unfavorable accusations, their close collaborators, partners and follower counts tend to fall off. But why is it that folks who promote misogyny, hate, and extremism are allowed to take up so much space and remain?
For many, when they want to start a fire, call attention to themselves online and via press, they ensure chaos and clicks with thoughts they likely wouldn’t utter vis-à-vis. In 2022, Akademiks and DJ Vlad bonded over Doja Cat’s dislike for them. That same year, DJ Akademiks pulled a targeted fake news campaign undermining Megan Thee Stallion’s credibility during The People v. Daystar Peterson, the trial that ended with Tory Lanez being found guilty of shooting her, only to admit Lanez’s wrongdoing after the verdict was announced. Most recently, this year, Latto confronted Adam22 after he made fun of her for interacting with someone who didn’t know who she was. “[You] wouldn’t try a male rapper like this,” she wrote.
“I really think they should keep that energy for men,” Caresha suggests. “And I really think that they should stop speaking on women because why the fuck you care? Whatever I have going on in my dating life, why is it important for you to speak on a female on your pod or whatever it is? You got so much shit to talk about.”
Caresha would know. She’s having fun with it, but she’s also using her platform to address serious real-life subjects, including mental health. In conversation with Chicago rapper G Herbo, she got him to discuss everything from how he deals with PTSD after the death of his brother to his past cheating tendencies, and, in turn, he got her to answer a couple of questions herself—including whether she likes gangsters or gentlemen and if she knew about Diddy’s baby before October—a rare mutually symbiotic moment that gave the host a taste of her own medicine. Her stretch of range is impressive. Caresha’s interviewing skills are perhaps best displayed on this season’s second episode, which led pseudo-psychologist rapper Kevin Gates—who’s usually stoic and clear in his delivery—to go from stepping over his own words to gleefully uttering, “This is my favorite show.” Coincidentally, it was also Caeresha’s favorite episode thus far. “[He]had my mouth to the floor the whole interview. I was like, ‘Are you for real?’”
Not everyone is ready for the smoke though, and Caresha’s aware of that. But she doesn’t seem to have trouble filling the roster. “They don’t even be coming to the interview thinking that they will open up or touch on certain topics… I know some people be like, ‘I don’t want to come on there. She’s too messy or da, da, da,’” she laughs. “But people really come on there and have a good time… that’s the most fulfilling part—people coming on the show, being open and really enjoying themself and being vulnerable.”
Her expertise and appeal lie not in academic study or the conflict-ensuing approach of some of her peers but in genuine interest in the unseen lives of her friends and equals. As is the case with traditional journalism and any medium that involves a mic, the wall of acceptability in what is asked to a stranger or acquaintance is torn, and she’s left pulling from the rawest of questions in her hat. “Do you like making love or f**king?,” she asks Diddy, “So many people speak [poorly] about having a BBL… how would you respond to that?” she asks Latto, or “Is it hard to not cheat while you’re on the road?” she asks G Herbo. It feels as if the viewer is peeking into a private chat between close friends—because, most of the time, they are. Unguarded, the familiarity of kinship allows for unhinged conversations.
“I know some people be like, ‘I don’t want to come on there. She’s too messy or da, da, da.’ But people really come on there and have a good time.”
She does all this while pushing DeLeón and her own products like the Resha Roulette, a card game that makes an appearance on each episode, which typically sells out, reminding us that the bag is the goal. With Caresha Please, Caresha positions herself as a savvy businesswoman, too, and wiith an average of 3.2 million YouTube views, she surpasses the viewership of her loudest peers.
Thus far, the show has featured three men and five women, and when I appear startled at the fact that Denzel Washington is one of her dream guests, she gets to the idea that guys make for great couch heaters and wild spitters. “I feel like guys are very interesting. I like to see things through their eyes. They think differently than women. So, I just really be wanting to know what’s going on in their head.” A relatable sentiment.
She has two more episodes to go to wrap up Caresha Please’s first season and doesn’t know who’s slated yet but has an idea of who she’d like to interview next. Future dream guests also include Lori Harvey and Beyoncé (to talk “girl things”). And as the show continues to solidify its identity and reach, artists are tapping her and her team to be on the show, too. Most recently? SZA. The two have yet to meet, but the thought of the union excites her. “She was supposed to come on the show and I was like, ‘Really?’” she beams. “I love that ‘cause I feel like SZA is very quiet.”
At 28, Yung Miami, which she describes as her more “savage alter ego,” has laid down many wigs (two in the span of our time together–one pin straight that wisped by her hip and the other right above the shoulder, giving her the air of an anchor); the mother of two has had a rather unconventional and specially configured path to stardom that makes her feel both new and seasoned in the space depending on the setting. Music is what got her in all of the rooms. A mere four years ago, Caresha, the rapper, and JT were signed to Quality Control. Their story thus far—unraveled and presented in docuseries form by both MGX Creative and Mass Appeal—is one of triumph. The duo became the first two women on the label, also home to Lil Yachty, Lil Baby and Quavo; they had little experience and two songs under their name, but QC’s co-founders, Coach K and P, saw into their future. City Girls released their first studio album, Girl Code, in April 2018 and had an affirming co-sign when Drake tapped them to be part of his song “In My Feelings” that July. The song was released with much of their original contributions chopped with the exception of their interlude, Drake name-checking them in the hook, and Yung Miami’s appearance in the video. It came out on the same day JT turned herself in for credit card fraud in June 2018. She would go on to serve over a year of her sentence, and her counterpart was tasked with keeping the entity alive and relevant, while pregnant. “F*ck that Netflix and chill, what’s your net worth?” she spits on the track.
Yung Miami has taken a backseat to Caresha over the last few months with the growth of Caresha Please, but she’s still top of mind for the multi-hyphenate. She’s well aware of the inklings and commentary surrounding she and JT’s partnership. Duos are few and far between these days, and women duos are particularly so, with Salt-N-Pepa paving the way for them to have a seat at the table, a mission many opt to fill alone. Recently, JT’s sentiments on things coming between them, shared in conversation with Angie Martinez on her IRL podcast, sparked skepticism on the future of the duo overall. But, Caresha is cocksure.
“I don’t think that we would ever split up. Sometimes we go through shit. Like sometimes, we not speaking months, weeks… I can think, ‘Oh yeah, I could do it without her.’ She could think, ‘Oh yeah, she could do it without me.’ But it’s like we’re better as a group. I feel like two is better than one,” Caresha says. (The two just performed at Dreamville Fest and are on the lineups for the Roots Picnic and Broccoli City Festival.) “I feel like the world can push ‘cause I read a lot of tweets and everybody like, “You want JT to go solo, solo, solo, solo, solo.” And when groups separate, it’s really, like, when you come out as a group, you better as a group… Sometimes we don’t feel like doing it. But I don’t see us splitting up. That’s not a worry, and I don’t see it. I don’t feel it. Or at least I just feel like I don’t see it no time soon.”
Despite being willfully and joyously tethered and in pursuit of further growth with the City Girls, Caresha is building a solo name and identity for herself on her own terms. In the music studio, she recently exhibited her pen’s chops with a quick dip into Lola Brooke’s fun forewarning track “Don’t Play With It;” her pithy verse proves she can hold her own. In the podcast studio, she further leans into that unabashed, raw persona by drawing inspiration from no one… except maybe Oprah.
In an off-the-cuff tweet from September 2022, Caresha called herself “The next ((((BLACK)))) OPRAH!!” She doubles down and explains, saying: “I feel like you have to put ‘Black’ in front of everything. Let people know it’s Black as f**k…I’m the next f**king Black Oprah. I’m the next Black young bitch that come from where Oprah came from. I’m going to be where she’s at. You get what I’m trying to say? That’s what I meant… Some people got it and some people didn’t. I wasn’t trying to take away from Oprah being Black. Oprah is Black.”
Aside from the obvious, Oprah was, too, a meteor-like arrival. Like the dichotomy of the persona and being, Caresha brings the smoke but is a breath of fresh air. She didn’t enter this space with the intention of being a disruptor but has already become one. While women continue to intentionally take up space in the hip-hop genre and its offshoots, and toxic men ideally déclassé as a consequence of their own actions, Caresha isn’t worried about the competition––because she doesn’t believe she has any.
“I’m never worried about what no man got going on. I don’t give a fuck,” she says. “That’s for your wife to do. Or your bitch.”
Joe Budden Argued His Way to the Top
Congratulations, Joe. You’re No. 1 on our first-ever Hip-Hop Media Power Ranking.
Thank you, man.
First off, I wanted to reveal our scoring system to establish this ranking. Here are the criteria: “Commentary & Banter.” What is the ability of the person to establish rapport with a guest, but also talk freely and fluidly about any topic? “Star Power of Guests.” How relevant, famous, and newsworthy are the guests this person books?
Mm-hmm.
Three: “Consistency.” How consistent is the cadence and volume of this person’s content?
That’s where I’m up. I got ‘em right there.
Four: “Viral Moments.” How often does this person produce a soundbite or interview moment that creates conversation on social media?
Shieeeeet.
And then fifth, “Content Integrity.” Is this person interested in actual journalistic endeavors? Do they promote false narratives and clickbait content?
Look at fucking Complex, pursuing the integrity of these people! I love that!
That’s where someone like Akademiks, for example, or Adam22, could potentially get knocked.
That’s where it gets tricky. Yeah.
So hearing those criteria, do you think we have the right system?
I think y’all got ‘em all. Y’all got the important ones anyway. Those are the sliders. I think everybody kind of falls under those. A few of those are high for me.
When I said “consistency,” your ears perked up. I think one way that you’re definitely winning is that you’re so regularly putting out content—whenever anything happens, people are flocking to listen to what your opinion is. How important is that for you?
One of the most important things for me. I was talking to my mom this morning and just catching her up on all the work I’ve been doing, and she said, “Man, you need a day off.” And I said, “I’m gonna take a day off when I’m 50.” By design, I just want to go as hard as I can go right now. So no vacations. Let’s get in there, let’s talk, let’s mix it up. I feel like in the sports world every day they have so many different things to talk about. And if you just try in the hip-hop world, I think we can come pretty close to it.
To me there are several reasons why you stand out above the rest. Great voice, obviously. The timbre.
Oh, come on. Off the charts.
You’re similar to the people who work at Complex in that you have a fast media metabolism—meaning you stay on top of shit. So when a Drake album comes out, or the Grammys or whatever, people want to hear Joe’s opinion on it.
For better or for worse. I can see it. That badge has come with its ups and downs. But yeah, like who else would I rather be than that person? That’s one of the reasons why I started doing it, right? Like I was a rapper and the people I was going to speak to didn’t really understand the plight of rappers. [The media] were kind of just doing their job, they got the little script in front of them to give the quick rundown on the person, then they get ‘em the fuck outta there in about 10 minutes. And there was so much more depth to it than that. For me it was, anyway. And clearly by the landscape, other artists out there felt the same.
It’s funny you say that because I just read a profile of you from back in the Everyday Struggle days. It said that when you were an active rapper you didn’t really appreciate bloggers and critics, but that doing the show helped you realize that the people who comment on rap generally love it and play an important role for fans.
Facts. I agree with that.
What do you think your role is as a media personality?
I think my role is to deliver perspective the way that probably only I can because my perspectives come from my very unique experiences. I kind of pride myself on being that Swiss army knife guy in music, right? Like, I’ve been robbed by managers, robbed by business accountants, robbed by lawyers, independent deal, major deal in a group—fucking, like, reality tv, digital mixtape, you name it. I’ve kind of been there a little bit. So that’s what I try to do. And the flip side of that is, I know most of the people I’m talking about, that’s where it gets tricky. So, I mean, you gotta be true to self and you have to be true to your relationships with all of these people. It’s a constant juggling act. Many phone calls, many texts. But I love it. I live this shit.
You were mentioning before that when you were a rapper and you were doing the press runs and stuff—
Hated them.
[Laughs.] Well it’s funny because back in the day, the criticism from rappers about rap media was usually that it was a bunch of white guys punching on keyboards. “You don’t know what I’ve lived through. You don’t know the culture.” And now the pendulum has swung entirely almost the other way where the people with the most powerful media voices are people like yourself and not that old stereotype. So now the debate is different: People on Twitter now argue over what constitutes journalism or what constitutes entertainment.
What do you think the difference is? Because yeah, it is a very blurred line.
There is a thought—and you might be an exception to this—that people aren’t actually really critiquing music anymore. Everyone’s just kind of ambulance-chasing and talking about the off-the-field stuff. But you see that with the NBA too, where off-the-court stuff is as talked about as what’s happening on the court.
I’m sure Adam Silver loves that. Right?
Yeah. So, do you consider what you do entertainment more so than journalism?
It’s 100 percent entertainment. It’s definitely entertainment. If it wasn’t entertainment, then I would be spending the night outside of NBC trying to get on their news channel. I’d be at Vice, “Hey, let me be your something.” But it’s entertainment first. It’s probably journalism second [laughs]. For me. Where I saw this thing going a few years ago was news, much like music, was kind of taking the backseat to brands and personalities. So everybody’s delivering the same news. We all have access to the same shit. But how? How are you doing that? Like, what makes people connect to you? What are you doing to establish a relationship with that audience? That’s been my “escape the room” math equation since 2001. How do I develop this connection with a fan through music, through TV? So that’s that same shit today.
Yeah, that makes sense.
And I’m a cheat code, ’cause it’s relationship equity. Got a lot of relationship equity with these people that I’m talking about. I love that.
I was listening on the way here to N.O.R.E. on your show. He was talking about something he said on his show that upset Peedi Crakk. He was essentially alluding to the fact that he’s gonna bite his tongue now about people who he knows or are his friends. And that goes back to the journalism thing—
See, that’s where it gets tricky. That’s where for me, because of my profession and just how I choose to live my life, I can’t be friends with y’all. I can’t be friends with these entertainers. I know a lot of ‘em, we got a lot of history, and we cool. But I cannot be friends with y’all, ’cause I’m gonna be loyal to me before I’m loyal to you. So if you go do some fuck shit and I read it and I feel like talking about it, I don’t want there to be so many instances where I say, “Hey, that’s my friend, I wanna skip over this.” I don’t. No.
That’s interesting, because N.O.R.E. obviously made the list, but I think N.O.R.E. wants to be beloved, like, the life of the party type.
But a lot of people do. A lot of people feel that way. I am the complete opposite. And I think that’s a positive, a plus for me, because I don’t need to be at your function, I don’t need to be at your brunch, I don’t need to be in your office. I’m not looking for a record deal.
You’re still buddies with rappers, though, right?
A bunch of them. Because I’m naturally me. And if you love that, then I will love you. But I’m not customizing myself for the gig. Or for the relationship, or for the invite to the popping party or for Grammy weekend. No. When these people hit me, “Joe, you out here for the Grammys?” N****, no. You know, I’m not out there. I don’t wanna be out there. I don’t wanna be next to y’all. I want to talk about y’all. I want to move right along with the industry from outside of it. I didn’t enjoy myself in it.
Is it fair to say that some of the rap media people today are bigger than rappers themselves?
Well, yeah. They are.
And I think that’s a crazy shift from even 10 years ago.
Well, shit, I learned that when I started working here [at Everyday Struggle]. Because I was coming in every morning with Ak and all the young people in my life were familiar with him. I wasn’t. So it was like, “Oh shit, this guy’s got some following somewhere.” Like, let me get hip. And then the rappers often will—let me find a nice way to say this—the rappers see the media people as an opportunity sometimes, and they will attach themselves or attempt to attach themselves to that person for rollout purposes. I’ve seen ‘em do it with Ak a million times. I don’t play with those games like that.
You mean, like, in the interest of promoting whatever they’re doing?
What’s happened to me a bunch of times is somebody got a project coming out and now they’re gonna just go out of their way to put themselves in the news to hear what you have to say.
Do PR people actively pitch you?
All the time. All the time.
But it feels like the guests who come on your show, it’s mostly you cold-calling them, and not a lot of staged PR.
Yeah, it’s not. When I worked here, I never liked publicists coming in here, giving us a list of things we can’t talk about. Publicists are there to ruin the interview. Normally they hear everything now when [they] leave, I gotta make a bunch of edits. But I have publicists that I’m fly with and sometimes publicists come through with the artists. Some of these guys are too big to not go anywhere without their publicists. But for the most part, nah, I try to stay away.
This is also I think a good evolution of what we’re talking about in journalism and entertainment and people like yourself. There’s less gatekeeping, it’s more authentic. So you get the bumps and bruises with that and sometimes faulty journalism. But it’s at least real, you know, there’s not a PR person breaking—
They’re there to step on the real.
Speaking of rappers being more famous than rap media, one thing I’ve noticed too is there’s this ecosystem now. So N.O.R.E. can go on your show and you can go on No Jumper, then Adam22 can go on Vlad, then Vlad can go on Akademiks—and you guys don’t even have to talk to rappers and get hundreds of thousands of views. That’s an amazing little cottage industry that you guys have built.
Yeah, no it is, it is great. And it can be bad sometimes. Like when I had Adam on, oh my God, that conversation lived for the next two months.
People defended Adam in that.
Oh no, they did. Yeah, they did. 100 percent. But I think as long as my message got to Adam, which I think it did, I don’t care what people had to say. That’s back to that integrity thing.
Well I don’t wanna re-litigate that conversation, I think it was about Kevin Samuels, R.I.P.—
It was about everybody. Rest in peace, Kevin Samuels.
It reminded me of this whole recent thing with Michael B. Jordan. Sometimes you take a purposefully contrarian approach just to incite the debate. Because if everybody agrees you have no discussion.
That Michael B. Jordan was one of those moments where it’s like, you could just say what you thought and what everybody thought, or you could spice this up a little bit. Yeah. That was fun. That’s fun in media. And shout out to Michael B. Jordan. Big Jersey.
OK, so we did a ranking and you came out on top. I didn’t wanna show you our full ranking, but I wanted to show you—
How many people did y’all rank?
Twenty-five. [Hands Joe the list of unranked names.]
Oh, whoa. Y’all gonna get people fighting.
It’s in no particular order. So take a look at it. I just want to hear what your thoughts might be.
Yeah, you know what? You could do 25 now that you look at this.
We could have done 30. Some people who you know intimately well were, like—
Teetering.
Yeah, teetering. On the edges.
These are the names here. Can I read? You got Sway, the O.G.
Yeah, got some O.G.s on there.
Caresha, who somehow won the new podcast award? She won some media award recently.
Everybody loves Caresha, but she got knocked for consistency because she only has eight or nine episodes a year.
And that’s why she probably shouldn’t have won the award. She didn’t have enough gas in the tank. But I fuck with the show, I love her. [Angela] Yee, another O.G. N.O.R.E. Big Boy—yeah, that’s those L.A. guys. Gillie & Wallo, for sure. Math. Pete… Pete still scrapping over here?
You’re talking about Rosenberg?
Yeah. [Laughs.] What the fuck he got going on?
He’s active! Juan Ep, Hot 97.
I don’t want to sound like a hater ’cause that’s my man.
There was some pushback on Pete and I actually advocated for him because I feel like whether you love him or hate him, his opinion does matter. Like when he says something on the radio or Twitter or on IG about rap.
I agree with you. It causes a little, a little stir.
It does.
I can see your point. Jinx, my man. Jason Lee, Elliott Wilson, me, Jazlyn. OK. Narduwar. How many times did Narduwar drop?
Yeah, Nardwuar was a controversial one.
Nardwuar? I hate to be the guy, because he’s a legend—
One thing we were talking about was like, do you get props for just going to festivals and red carpets or whatever?
No!
But—Nardwuar got Hov, and he’s got Tyler, Uzi, people that we can barely get, you know? So he has power, in that sense.
And he’s just been around forever, and he has his own shtick that nobody else does. So, I mean, I can’t argue with him there. But I don’t see Narduwar enough. I don’t want to get to his age and people say that about me, too.
You’re saying you’re younger than Nardwuar?
I’m 100 percent younger than Nardwuar. Please, please fact-check this for me. He’s been around forever. He’s from radio in the ’90s. [Editor’s note: Narduwar is 54; Joe Budden is 42.]
My mind is blown.
Vlad. Can’t hate on Vlad. Ak, Ebro, Fantano—Anthony’s here—Charlamagne, uh, Kai. Yeah. I’m anxious to see how y’all ranked this out, this top 10. Well, Angie and Nadeska, Angie is making a really strong late push. She’s been going crazy the last few months.
Yeah, her booking power.
She’s a mentor. I think we mentor each other.
Back in ’04 when you were doing your broadcasting debut for Hot, she was there, right?
Yeah, but fuck that. Angie was my friend somehow. Like I had met Angie back then and we clicked, and we became friends that lived down the street from each other. So while I was in my deepest, darkest days of independent rap, struggling check to check, trying to make things work, I saw Angie thriving as the voice of New York and media and interviews and just class. Just the way that she was moving was inspirational to me. Yeah, she’s great, yeah, she’s a legend, yeah, all of that history—but how she impacted me on a personal level, and still does to this day, I’m forever in debt to her.
Yeah, she’s a legend.
A few people on this list that inspire me, actually.
Peter Rosenberg?
Yeah. I mean, at one point, Pete helped me get my podcast number one off the ground. So, I mean, I can never say a bad word about Pete. Look at Flex! Oh yeah. This is gonna be… y’all are gonna get a lot of people fighting.
Yeah, we are. You know what’s interesting too, when we were putting the list together—you see Angie, Angela Yee, and a couple of wild cards, but for the most part, and especially in the top 10, it’s mostly men over 30, over 35. There’s not a lot of young people and there’s not a lot of women who are in punditry.
Well, in rap.
In rap, for this particular genre of talking, it feels like there’s not a lot of young people who are throwing their hats in the ring in terms of commentary. But you have someone like Kai [Cenat]. So I’m actually curious about your opinion of someone like Kai or Adin Ross, even if he didn’t make the list—
Adin Ross should’ve been on this list before a few people.
I think Kai trumped him though.
Yeah, but he still should’ve beat a few other people that made this list.
What’s your opinion on Kai and the rise of the streamer? That’s the next evolution of this entertainment journalism, where Kai just gets Lil Baby to hang out with him. He’s not even asking him questions, really. They’re just chilling and conversating, and that now is how people wanna see their rappers.
I love it. I love it. I think that that is part of the evolution of this thing, and where this is headed, where it’s going. It’s part of the ecosystem. Everybody gotta feed off of each other. So to see this guy sit in whatever room that is and have everybody in the world go there and just sit there and listen to him—I can’t even critique it, because I don’t know what’s happening. But I know there’s a large audience and all of my nephews, little cousins, and everybody fucks with him. And I seen him in the strip club a few times. Cool little dude.
They get sturdy on his streams.
Listen—I say all the time: We gotta stop beefing. Because everybody here has a place, and it’s important. Every rapper don’t want to go to the same people to say the same thing or do the same thing. Right? Like, Nicki [Minaj] will call me however many times because she’s comfortable with me and how we deliver or present her story. [Lil] Durk will go to Gillie with a million dollars and take him to Chicago and I’m sitting in my house like, “Oh my God, what the fuck? [Laughs.] How are they doing that?!” But we need that, ’cause I wanna see it. Jason Lee, he’s got Cardi, right? Like I know Nore was a little tight at that for a second, because we all have these inner little wars who gets who, who does what. But everybody here has a very important place. And all the musicians, we need them.
So you’re generally congenial with your competition?
I don’t think I have any competition. I don’t think none of ‘em could fuck with me. I don’t put myself in that. I’m like a deranged, psycho, perfectionist Virgo with OCD. So the bar that I set for myself is gonna be higher than whatever bar these people could set for me. Like I need to be in competition with my last interview, or my last outing. I need to see how this looks from the Yachty interview on Everyday Struggle, which was my very first sitdown with somebody—
You were moving around for a lot of it.
—to how do I listen more when I’m talking to Rob O’Neill from the Navy Seal Team Six. Like how do I listen and just be engaged in that? It’s just different things that I wanted to learn, and I’ve learned from a lot of these people, but I’m competing with me and me only.
Someone whose name came up on the N.O.R.E. episode with you is Taxstone. If Taxstone hadn’t gotten into the trouble that he did, do you think he would be on this ranking?
I say all the time: If Tax was out, he would be at the top or very near the top of this list. He was a force, he was a force to be reckoned with. I was gonna have to deal with that for a few years. And, if he’s lucky enough to come home, I’m still gonna have to deal with it, because he’s great. He’s great. No doubt about it.
From your brief stint on Hot 97 in 2004 to Everyday Struggle to now, how do you think you’ve gotten better?
Listen: On Hot 97, I was… I mean they think I’m politically incorrect now? The things I was saying on that radio before there was a delay? Oh my lord, people were lined up to beat me up outside. I remember we had Ron Artest come up there and I said something real stupid to him. And everybody in New York knows that you’re not supposed to say something stupid to Ron Artest, the last person. Oh my God, it was a nightmare. But I was a baby. So then you come up here, to Everyday Struggle, I do my Yachty thing and that goes the way it goes, just because passion is blurting outta you. But then you go home and you learn that your passion is not received as passion. You look like a fucking insane lunatic. So [laughs], you gotta switch that up a little bit.
And there was the Migos incident.
That Migos shit was… that was the biggest one of the year, and Complex didn’t wanna put it out, goddamnit.
I wasn’t there at the time, so—
I know, I know. No, that was a judgment call for me. “We’re putting it out and they can deal with me. If they want to fire me, fire me!” [Laughs].
Is there one thing that you attribute your success to, in this realm as a media personality? Is it outworking the competition or a combination of things?
It’s probably gonna be a combination. Outworking people is one of them. But I mean, like I tried to say earlier, I designed my life for this. Everything else is coming second to the gig, at least for now. But that’s will too, right? Like, to outwork people that way, your will has to be strong. You have to just want it more. I’m a Knick fan. I could tell when I’m watching a Knicks game when the other team just wants it more. We just lost that last game to Charlotte, up 19 at the half or whatever it was, because they just wanted it more, and you could see that. So yeah, will is important. And, you know what? The audience, ’cause we don’t even have all the control. This audience is gonna change every four years, five years, you know what I mean? Everyday Struggle was 2017. That was six years ago. So for me that means that today there’s a 16-year-old out there that is trying to learn and see what’s going on that might not have been watching us when he was 10. Like my oldest son, I watch him and his journey at 21, I think back to me at 21. I was getting my shit from hip-hop, rap, the interviews, Fab 5 Freddy, fucking Dr. Dre, Ed Lover… the guys! Yeah. So we want to be those guys for the youth, and continue the chain.
In terms of your podcast now, do you feel like this iteration is the best it’s ever been?
Do I feel like this iteration is the best it’s ever been? I’m gonna say yes, because of the plan. I wanted a woman on my podcast since day one. The entire time I’ve wanted one. I’ve always wanted a panel. So even if my old co-hosts were still there, I was gonna add. So the fact that this is closer to what I envisioned and what the plan is, yeah. And I’m not done man. I’m not done. I’m kicking ass. I’m on they ass. Everybody.
We could probably end it there, but I have a couple more.
Give it to me.
You were talking about Yachty actually.
My man.
Back in that 2017 profile, you said:, “If Complex wasn’t paying me, I would never talk about Lil Yachty.”
[Laughs.] What a dick!
That moment between you that happened not far from here, when you were screaming at Yachty, was like the perfect old head vs. new head argument, and that’s why that thing went so viral. Can you reflect on that moment and also how you may have changed since then?
Even listening to that quote. I was super wet behind the ears in terms of doing the interview, what I wanted to convey or get out the person I was interviewing, I just didn’t know shit about shit. But that was kind of fly. That’s what they say, if they say I’m missing my edge, that’s what they be talking about. But I’ll never do that shit again. But today? I learned from Yachty, I learned from Quavo, rest in piece Takeoff. I learned from that moment, Offset. I learned from each interview that I do. So the next one could be better. I’m still not all the way there. Like, I watch my shit and be like, all right, we need to fix that up, make a couple of changes here and there. I’m committed to the work. It’s always a work in progress and I’m just committed to doing the work. I know that sounds really cheesy when you write it, but that’s just the truth.
I’ll close with this quote you said in 2017: “I never really identified with being a rapper, if we’re being totally honest. Rappers drink. Rappers smoke. Rappers fuck a whole lot of women. Rappers go to clubs every night. Rappers stand on couches. Rappers carry weapons. Rappers want to fight everybody. Rappers are tough. I’m not any of those things.” What’s your reaction to the quote today? And do you think this version of yourself, which is the most powerful hip-hop media personality, was always going to be your final form?
Today I think that quote’s bullshit. [Laughs.]
Because you’re standing on couches?
Well, because that’s the wrong idea of what a rapper is. That’s what I hear today.
Probably ’cause you were more bitter about rap back then, maybe?
Well maybe because at the time of my entry, that’s what they were urging me to do or urging rappers to do—which is be seen, be around a lot of women, cause chaos. That was in ’01. But a rapper didn’t have to do that. Like you could still be a rapper. And that part is missing from the quote. And, at some point in my journey, I tried to go do all of those things, except for the “be tough” part. All of those things I tried to go do, so I could be a rapper. But the truth, if I just had a better understanding of my own value, then I maybe would’ve changed what rap or a rapper looked like at the time. That’s what I think of when I hear that quote now.
Yeah, and that’s obviously changed since the late ’90s and early aughts.
Thank God.
You can be—
—whoever you want to be today. You can be Lil Uzi with a fucking house record going number one. You can be Cyhi and Pusha, you can be lyrical miracle, you can produce, you could write for people, you could be Yachty—it’s so many different things you could do today. That sounds ancient. And you never want to sound that way when you’re dealing with art. You want to be as timeless as possible.
What’s next for you?
Oh, I got a second wind. I’m rejuvenated. It’s like I just woke up from a nap. I’m ready to kick ass. Like I said, I got big plans. I want to continue to develop my vision—I can’t share because the competition is right above me on the list. But there’s a lot of things I want to do. I’m anxious and I’m passionate, still. Like that’s always the scariest thing for me. In rap, it was, damn, I can’t even imagine a day where I don’t want to rap. Like that’s scary where I don’t have the passion to do it. But then that day came, and it was fine. Same here. It was like the day where it feels like you’re getting up and going to work, then I don’t want to do it anymore. And by the grace of God, that day is nowhere close.
I was listening to Bill Simmons on the How I Built This podcast and he said a couple of things that resonated with me. One is that in the business of content you can’t run the same thing back every year and grow. And two, the people who actually give a shit will always be the most successful. It sounds like both are on your mind.
For sure. And will remain at the front of my mind. I’m not letting up on these dudes. [Points to list.] There’s some talented people here. Better keep up.
Hip-Hop Media Power Ranking
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Jazzy
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Nyla Symone
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Sway Calloway
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Nardwuar
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Anthony Fantano
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Nadeska Alexis
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Adam22
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Big Boy
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Brandon “Jinx” Jenkins
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Peter Rosenberg
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Funkmaster Flex
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Angela Yee
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Ebro
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Angie Martinez
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Jason Lee
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Math Hoffa
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DJ Vlad
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Elliott Wilson
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Caresha
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Kai Cenat
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N.O.R.E.
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Gillie and Wallo
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Charlamagne Tha God
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DJ Akademiks
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Joe Budden