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How does one interview someone who’s interviewed most—if not all—contemporary hip hop artists out now? Someone who’s worked at magazines that are institutions in the genre? For the most part, I have a connection or a relation to the who and what I write and shoot, so when I was asked if I could interview Elliott Wilson, whom I met once before at a event, I hesitated for a bit, jotted a few notes and replied, “Sure!”

I read whatever info was out there, Wikipedia entries and other pieces. I watched some episodes of The Truth on JAY Z’s Life+Times YouTube channel, and checked out Rap Radar just to try and get a better understanding of who Elliot is and how one interviews the interviewer. It wasn’t until I sat down in front of him and we started talking and I started listening—listening to how he started and his approach to doing what he does and has done—that it started to come together. There’s always a point where an interview turns into a conversation, and the person you’re interviewing simply talks to you and you listen… and there’s a flow. It’s difficult to do, but as Elliott says, “There’s a finesse to it.” Over the course of his career as a music journalist, due in part to his being an active participant in the culture, and someone who truly lives it, he has mastered this finesse with the artists he’s interviewed. In the brief time that I spent with him in his Soho office at Rap Radar, I had a better understanding of him and how he does what he does and why artists respect him, even when documenting their personalities surfaces differences between the documentarian and artist. “I’m not a tough guy, but when you write something and do things and you make decisions, you have to stand by your word... What you say, hopefully, has power,” says Elliott. Read our interview below where we discuss respect, advice to budding music journalists, misconceptions in the industry, and channeling anger in a positive way that can only keep driving you further.

You’ve interviewed everyone from Lauren Hill to DJ Khaled. When talking to such diverse and strong personalities, how do you keep the conversations so vibrant?
I think the thing is that with my interviews, it’s become its own monster now... I think for the last couple of interviews I’ve done with, like, a Jay-Z or a Drake—they really stand out and now people are recognizing me for my interviews. And all I really try to do with interviews is try to a lot of research, be really well-prepared, and I try to ask the questions people want but achieve that by creating a conversation. I think one advantage is that I put my work in. I’ve been there for a while. Artists have respect for me, even if we don’t always agree on things. They respect my work ethic and see what I’m doing and know that I’m a great platform for them to get their vision across.

It’s a little bit of both, but I think I’ve done a great job at becoming a better listener, not talking over people—which I always used to do to try to get that gem. I’ve learned to be a little more patient... [Sometimes] these artists know the negative or controversial content you want to ask them. It’s really how you ask them and how you get them to open up on it—there’s a finesse to it. Or, “How do I ask this question in a way that’s going to open dialogue about the subject that’s not necessarily a subject this person will want to talk about?”

When did you realize that writing about music was what you wanted to do?
First, it was writing about sports. I thought I wanted to be a baseball player and my dad wanted me to be one. I started not having the desire to play as much as I got towards the teenage years [and] I didn’t think I was good enough to go pro. I always said I was supposed to be Derek Jeter—that’s how I was raised, I was biracial and supposed to be shortstop for the New York Yankees. So I was like, “Okay, I can’t be the athlete. I love sports, I wanna be a sports writer.” I used to love Howard Cosell, Warner Wolf, the Newscasters. I used to read the newspaper writers and the columnists in New York so I was like, “Let me write about sports.”

But then hip-hop started taking over my life more and more—this is late ‘80s early ‘90s. I started seeing The Source and I was like, “That’s kind of more what I want to do, I want to write about this music.” I always felt that it wasn’t being treated with respect, and no one understood [how] it was changing my life and that it was special. And here was a way I could make money doing it. So I was like, “I gotta be a music editor at The Source.” That was my career goal.

You started Ego Trip too, right?
Started Ego Trip first, yeah. Because Ego Trip basically came out of the fact that we wouldn’t get recognized. I would write letters [to The Source] and try to get down and I got rejected. That’s when I met Sacha Jenkins and Haji Akhigbade. He had just started an independent magazine called Beat Down. They did one issue with Cypress Hill was on the cover.

I kind of knew Haji from college and Sacha from high school, and it was like, “No, we do our own magazine, we do our own newspaper, we do our own product.” And I was like, “You can do your own newspaper, your own magazine?”

We did Beat Down for about a year and a half, and then Sacha and Haji had differences. I was like, “Sacha, we should do our own magazine, our own newspaper. And it should represent you teaching me about culture in terms of graffiti and all these other things that are going on. It’s not just hip-hop.” And no magazine that was a hip-hop magazine at that time was really that broad, that independent, and with that mindset that we’re really covering graffiti or rock culture or skateboarding... We had a clear vision and could do something different. And out of that came Ego Trip.

So by doing Ego Trip, it’s how I got the job with The Source and how Sacha got a job at Vibe because people started recognizing, “Oh, this is a dope zine, these guys are talented, who are these guys?” It was really doing our own thing that led to me getting the job that I thought I wanted for my whole life—music editor at The Source.

So eventually, it led to you being the executive editor at XXL.
Editor in chief. Source music editor, I did that for two years – ’96 to ’98 – left on bad terms, I wanted to be better than them. Well actually, I threw myself into the Ego Trip rap list that we were working on, so I worked really hard on that, I’m really proud of that book, I think it’s one of best if not the best books on hip-hop still. And then about a year into that they approached me about the XXL job.

I was like, “Wow, could I really be that boss—Editor in chief?” Could I do it? Could I run it? And I went for it and my whole thing was to try to really directly compete with The Source because I was really angry about the way things ended. So it became this real contentious thing. So that went on for about nine years until we were finally able to outsell them and it was a crazy exciting time.

I’ve gotten salty, personally, situations have made me salty and it just makes you go harder.
Yeah, exactly. People say, “The worst thing someone could say to you is that you’re bitter.” Because bitter is really dismissive and you’re just not coming to peace with something wrong that happened, or you’re not doing anything active and you’re just known for the fucked up thing that happened to you. So you can either be that and be in a state of what people call bitter, or you can take that aggression and anger and use it in a positive way. You can make yourself work hard and push yourself and figure out what you want to achieve and redefine yourself.  If I didn’t want to be the guy that quit The Source, or the guy that got fired from XXL, I had to keep doing other things. You have to keep defining yourself.

For budding music writers and aspiring journalists reading this, what would be your top three rules or words of advice?
Do your research, that’s the un-glorious part of it. The beauty of the Internet now is... There’s so much stuff online, there’s Wikipedia, there’s artists’ discographies right there, there’s mix tapes, there’s albums—all the information is there. But you really have to take the time to get into it and connect to it. Download all the music, read a lot of the articles that are written about the person, and see what there is to really talk about them. What do people want to know? What do people want clarity on that they don’t know? What hasn’t been explored or discussed with this person?

It’s about taking advantage of the way the world is now. Yes, it is one big glorious mess and some if it is erroneous that’s out there, but a lot of information is accurate out there, and you have to figure out which is. And then you gather than information and use it to your advantage.

I guess, secondly, be a good listener. It’s a challenge when you’re younger because you have your ideas of what you want. You tend to talk over people, you’re excited, and you have to learn that you don’t control the pace—they control the pace. You have to be somewhat deferential to the subject that you’re talking to, to make them feel comfortable. You have to be respectful to them and follow their train of thought and not just push what you want to talk about. Try to guide it by listening to them and asking the right follow-up questions.

And then the third is really just work really hard. Approach it like a job. Approach it like it’s un-glorious. Approach it like it’s a job, like you have to be there at 9. Do as much as you can to turn it into a professional thing without suits and ties and bosses and someone breathing down your neck. Everybody wants a career, but they don’t want a job. Surround yourself with people that will hold you accountable to that. Because, I think, at the end of the day, you’re going to get better results that way

What is a misconception about working in music journalism?
I guess that the artists are your friends, that it always doesn’t lead to the same things, that it’s about respect. That if you are true to yourself and responsible, there are going to be times when you have differences with the people that you document. There’s going to be times when you’re on good terms, and times when you’re on bad terms. Most of the relationships work that way... I think the lines get blurry of who is really down with who. There’s no real royalty to it at the end of the day. It’s about respect, it’s about communication, it’s about wherever this artist is in their life and what you can or can’t do for that person in the moment. And you ride those waves.

I think it’s a misconception that you can’t be critical [or that] you have to be down with everybody. At the end of the day, you have to trust your instincts. You have to be true to yourself, and you just gotta be a stand up person with people. I’m not a tough guy, but when you write something and do things and you make decisions, you have to stand by your word... You can’t hide behind things—you put yourself out there. What you say, hopefully, has power. The words you put out there. So you gotta be responsible and willing to accept the ramifications of what comes with your voice and your words.

That’s never gonna change whether you’re doing it on Twitter or doing it in a written New York Times article. Nowadays, it’s a very blurry line in that sense.

Any final words, thoughts, thank you’s?
Thanks to The Hundreds, taking the time. Shouts to Dezi, Taylor, the guys that helped me with The Truth. Like I said, I’m really proud of this season five that we got. We finally have a good feel of what we’re going for with the series now, and redefining it. I think it’s shot really well… This season, we did Freddie Gibbs, 2 Chainz, Hit Boy, Action Bronson. We have a pretty good season of content and we’re proud of it.



Watch episodes of The Truth with Elliott Wilson here on JAY Z’s Life+Times channel. And keep up with the latest in Hip Hop on Rap Radar.

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