Dante Ross on His New Book and Chicago Hip Hop

Standing as one of last the authentic "Record Men" in the industry, Dante Ross carries a legacy marked by triumphs, setbacks, and constant reinvention. A quick glance at the artists he’s worked with reads like a roll call of hip-hop's most innovative talents: Brand Nubian, De La Soul, KMD, Queen Latifah, Ol' Dirty Bastard, just to name a few. His name has been mythologized just as much for his contributions as the fiery exploits that defined his early career, including an infamous altercation with Diddy at a New York club.

In his recently released book, Son of the City, Dante unravels his life’s story, beginning from New York's Lower East Side to his ascent as a major player in hip-hop's major label realm, replete with its glitz and facades.

Initially conceived as a joint memoir with his father, the activist and writer John Ross, the book finds Dante reconciling his complicated upbringing while taking responsibility for his choices and actions. All interwoven with engaging anecdotes about some of the most influential artists and albums in music.

In part written as a way to let those close to him know the motives behind some of his actions, the intimacy provides readers with unparalleled closeness to stories that shaped hip-hop. Dante remains a candid straight shooter —though now tempered by maturity and experience—unflinchingly addressing the milestones and missteps in his life and career.

Dante will be in Chicago this Wednesday, August 16th for a book signing event where he’ll delve into Son of the City and a vinyl DJ set. In our interview below, I asked him about Chicago’s own Monica Lynch, almost signing The Cool Kids and naturally evolved into his favorite rappers the Windy City has produced. Notably, he demonstrated an impressive recall and connection to Chicago, listing over a dozen names of Chicago talent and sharing his admiration for their work.

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Now that the book has been out for a couple of months and you can revisit it without being in a writing mindset. Have you found that it unlocked any new emotions or perspectives outside of what you were already kind of uncovering when you were writing?

I think on the emotional side, yeah. I think there are a couple of things in a book that I wish I could redo. Two particular things: I kind of misstepped on my Five Percenter breakdown and I wish I could do that again. That's one thing. That information was available to me. If I'd just asked some friends of mine. As opposed to reading online about shit. So that was, that's one thing that perturbs me —and my editor was a little sloppy in a few places, and that bothered me. But when we talk about the emotional aspects of the book, I feel good about it all.

I feel like what comes back to me from people who have read the book is often, they're surprised that the story that's not musical. The stuff that doesn't deal with the famous people I worked with. And I think that that's cool. They're always like, "Wow, your childhood was fucking wild, super crazy. Your family dynamic is nuts. And the fact that you were vulnerable enough to talk about all that stuff was really cool." A lot of people have, you know, taken me aside or hit me on DM and be like, "Yo, I had similar shit in my life. So I think that that vulnerability touched a lot of people and to me, that's really cool. That was maybe the hardest part of the book to write about and most purposeful.

I'm sure that it also helps people understand you more.

Yeah, and that's part of it. Look, I felt like I might owe some people an explanation. I have a good friend of mine, I'll leave him nameless, a famous guy who I've known a long time said, "You know, when I read the book, it explained how unhinged you were when we were younger" and I was like, "Oh yeah, you guys didn't know that stuff."

And he was like, "No, man, I had no idea. Now it all makes sense to me." And I thought that was cool. I don't spend my life explaining myself, but it shows why I behave in some of the ways I behave. So I think that's cool. It sorts out the puzzle.

What I know of you is that you've always been candid, and the book, as you said, was extremely transparent about both your highs and lows. But was there anything you almost left on the cutting room floor that you felt like this might be too personal, too deep?

I don't know about too deep or too personal. There was the one thing about my sister's friend trying to molest me. That was tough. And I don't know if I needed to have the me and Diddy get in a fight story 'cause everyone's heard that story so many times I was like, "Well maybe it's gratuitous." But I left it in there, so those were the couple of things I thought that maybe could've got the snip. 5hat and the Five Percenter thing really that's it really. I mean I am a pretty candid person and I'm not really running for office, so, you know, no real regrets.

I thought it was pretty cool that, which you kind of reiterate just now, in the book you mention something along the lines of wanting to tell your whole story because it's important since just knowing what music you listen to doesn't really give you the full context of what influenced your music taste. I think that's like true for every type of listener, but especially for people that are involved in a genre like hip-hop. Was writing the book, a great opportunity to revisit all those moments that led you to, to finding the genre?

I wrote the book over such a long period of time, but yeah. I've always been relatively aware of why I was so attracted to hip-hop and why it was easier for me than many. I thought it was important to tell that. Whether people's perception of me is one thing or another. I grew up surrounded by the culture that would evolve into hip-hop. And I thought it was important to tell that story. I grew up in an era —the seventies—in a culture where music was heard outside, at block parties, and coming outta cars and in the street, and this music I was exposed to as a child ended up becoming the foundation for hip hop.

So I was, whether I knew it cons consciously or not, I was tied to the mass of the foundation of hip hop, at a very, very early age. So, when the sample era started, the golden era, and people started sampling records, I knew these breaks and when I went to hear people like Afrika and Afrika Islam at places like the Roxy, I was familiar with a lot of these records already. I knew “Apache,” I knew "It’s Just Begun," I knew these records. So for me it was, a kind of like second nature and hip hop is, or was composed of many parts. A great collage. My childhood and the culture I was raised around in New York City, is part of that collage, the many different facets of it.

I think now with the internet, it kind of detached itself from all the core elements that you, especially like growing up before, like you needed to be involved in.

Right, it couldn't be visceral. You had to be there. You had to be outside and, you know, I was outside.

I did not know that Monica Lynch was from Chicago. That was a cool tidbit from your book that I found.

Not only is she from Chicago, but she's also really proud of being from Chicago.

And Midwesterners typically have like a different personality than people from the coasts. Did you find that to be true when she was already working over there? Or was she already acclimated to the scene?

That's, that's interesting. She's a very, very nice person and I didn't spend a lot of time in the Midwest 'till later in life and I find people in the Midwest, in Chicago, are much nicer than people in New York. They're way nicer. [laughs] In general, a pretty congenial kind of person in Chicago. I know Chicago people, they have their own thing: a lot of heart and a lot of soul. I don't know the Midwest all that well, I know Chicago and I know Detroit. I don't really know anything else but, I don't want to offend anyone, but I think that's probably the stuff worth knowing in the Midwest.

We're now technically in the Chicago portion of this interview, and I also saw that you wanted to sign The Cool Kids at one point.

Not only did I want to sign The Cool Kids, I ended up becoming good friends with The Cool Kids, Chuck and Mikey. I was a huge fan. They started the whole blog wave of rap. The rebirth of that was put forward by them and the Fools Golds guys, Kid Sister, that whole vibe. I thought it was fantastic and I literally went to Chicago several times to try to sign them [to SRC], I was the vice president of A&R there.

We flew them to LA and unfortunately, they had signed a deal that kind of handcuffed him. They had a manager at the time who just didn't know what the hell he was doing and nice guy, but he didn't know what was up. He signed the deal and he kind of fucked their whole thing up. They should have become one of the leaders of all of this, and they didn't because of that deal that they signed.

It was ignorance and, they were ahead of the curve and I mean, gold and a pager, like bringing 88 back, "Black Mags," they were great. They were so ahead of this thing, and yeah. I firmly believe that if I had been able to sign them, or the multitude of others who wanted to sign 'em, including Interscope and all these other guys, if that had happened, they would've been a world-famous act instead of a seminal act.

And I thought Chicago at that time in music, the Cool Kids were at the forefront of this whole thing that happens in this time period. It becomes, you know, Savemoney, certainly [are] the nephews or the little brothers of those guys. So whether it's Mano and Holt, or it's any of those guys, they all became very important. Kids These Days, Chance Rapper. Even King Louie, who's another side of the coin, or Chief Keef. They all became part of this. I mean, I went to Chicago and I remember my friend Hustle Simmons showed me Chief Keef when he first came outta jail. He was like, "You need to sign this dude." I didn't do it and I should have. I've always keyed in on the talent in Chicago. At least since that era. I guess Kanye opened the door for us to know about Chicago —Common and others—but it was in that time period that the Cool Kids [led] to the Savemoney period to Saint Alfred, Leaders, all the shit that's going on. Even Bibby and Herb were a part of it. I tried to sign them when they were still a group 'cause my man from Leaders put me up on 'em, Vic [Lloyd]. Mick Jenkins is part of it. The talent pool in Chicago at that time period was, I think, unparalleled by the rest of the country.

I would always say that Chicago, it's like New York in 2000, everyone could rap good. New York in '99, everyone's nice. There was such a deep pool of talent and I was inspired by it, I gotta tell you. It was inspiring and I was lucky enough to know the guys at Saint Alfred. I knew the cats of Leaders. I knew Mano, I knew Holt. I got to know Chuck. I knew Big Chris and all these guys out there. I had access to the world of Chicago that most don't get, and I spent a lot of time there for a couple of years. I really loved it. I really loved all the music that was going down. I tried to sign Chance when he only had 10 Day out. At Congress Hall, which was a show was him, Spenzo, King Louie, Alex Wiley, and some other group that was popping at that time period. L.E.P. Bogus Boys were there. It was a fucking grimy environment, big ass space, Congress Hall and Chance bodied that shit. And I was like, "I gotta sign this guy.” That's where I met Pat and those guys. And I never got to sign him, but man, I was a fan of all it. Vic [Mensa], the Closed Session guys. A lot of cool shit going on back then.

You kind of took my next question which was, are there any other Chicago folks that you are checking in [on]? Either present or from the past, but you just confirmed that you were plugged in at that time.

I knew all of it. And, and I still think, there are good things out there still. I tried to sign G Herbo to Atlantic and we fucked it up. We fucked the deal up. We had it, and there were some things going on behind closed doors that screwed the deal up. But I'm, I'm good friends with Mikkey Halsted and he's kind of one of my cheat codes out there. He knows everything. He's the mayor.

I've always loved the energy of Chicago. Of all cities in America and people in America. It's the most New York, maybe San Francisco. But I think it's Chicago 'cause it has the weather, it's a tough place, it's not for the week and it's also got a lot of heart and soul the way New York did before all the transplants came. I don't know if it still has it, but Chicago still has it.

Are you familiar with Saba?

I love Saba. I love Pivot Gang. I tried to sign Smino. All that stuff is great. Monte Booker is fucking genius. Yeah. You know, there's so much good music out there, man and it's not going anywhere. Ravyn Lenae. There's just so much good shit, man. There's always something great in the water out there.

Our publication is focused on Chicago's music scene specifically, so it makes me happy to just hear you name all these names. The moment you mentioned Hustle Simmons, who's a legend, I was like, "Okay, he knows."

He's an old friend of mine. Um, I know him since he was like a baby damn near. [laughs] He was a youngster. I've known Mikkey for a long time [too]. I go back with Mikkey and Chicago has, I don't know man, Common, Kanye, Lupe [Fiasco], and Mikkey, those dudes all rap really good so to me, that's like the DNA of Chicago rap and it just goes from there. They are prototypes and were bad motherfuckers, so of course their offspring, their children will be equally nasty when it comes to rapping. I love it, man. Flosstradamus was part of it. I was good friends with Melissa [Kid Sister], Kid Sister was my home girl. She's like a little sister and that whole shit was so cool back then, man. It was a real energy going on and I wish I had been able to figure out how to make some of it come to the forefront. I never really did, but man, I'm always looking for stuff from the Midwest, Chicago, and Detroit. There's a lot of good music in both those places.

Yeah and, to your point about the similarities between Chicago and New York, especially reading your book, a lot of those names that you just mentioned, they either work together or they're friends or they were just at parties together and they all just created this sense of like, Improving the, the quality of the music and, and coming out with some really awesome stuff.

I mean, even the drill guys could rap really good for gangster rap. Durk was dope. Reese was dope. Those guys, they all had some shit, man. That whole Chief Keef wave and all the stuff. Them dudes were definitely making street music, but they were rapping really fucking good. King Louie was really good. Reese was really good. They all had some shit. I thought they all were dope.

You'll be in Chicago next week for the listening party. How did that come about?

Alex [Fruchter from Closed Sessions] hit me up. We'd done stuff before; I brought Roc [Marciano] out there, we did stuff with Action [Bronson] out there very early on actually. We brought Action out there, that was one of our places. I saw Smino's first show there too. I went to Schubas to see that. So I don't know, man. I'm friends with him and we just figured it out.

I'm jazzed, you know, I DJed Soul Summit a bunch of times too, which is like this huge vinyl soul party in Chicago. It's the biggest one in the country. With Dave Mata and Mo Manley and those guys. I've done that several times the last like pre-pandemic years. There's a varied culture in Chicago. I've always had connections there. The was also a lot of great rock music from Chicago, whether Smashing Pumpkins or The Orwells or Smith Westerns, Urge Overkill, on and on and on. There's always been a serious music scene there and I've always been kind of tapped into it. There are five or six places in the country I always kind of revisit and I can always like just tap in. And Alex is my guy there. He's one of my guys in Chicago. I've stayed friends with him for a long time. I always loved the studio. I spent a bunch of time there over the years. We're friends and fans of each other and it seemed like a cool thing to do. So I'm psyched.