Q&A: Reggie Ossé on becoming an accidental interviewer

A great interview is one of the journalist’s most powerful tools. It can be informative, entertaining, thoughtful. For the next five weeks, the Columbia Journalism Review and MaximumFun.org will broadcast conversations with some of the world’s greatest interviewers. Hosted by NPR’s Jesse Thorn, the podcast, called The Turnaround, will examine the science and art of journalism.

This episode features Reggie Ossé, the host of The Combat Jack Show and founding partner of the Loud Speakers Podcast network. An edited transcript is below.

 

THE ACCIDENTAL INTERVIEWER

Jesse: Why on earth would you decide to go into this field? When you have skills!

Reggie: Well, you know, it wasn’t planned. I think I mentioned this to you before. I totally burned out in the music industry. Initially, I was a fine arts major. So I always craved being in a creative setting or creative surrounding. I got burned out, dude. And when I got burned out, I just stopped doing everything. It was literally a meltdown, and the only thing I could do at the time was start blogging about my experiences in the music industry. I started off with this insanely profound, but evil, genius blogger by the name of Byron Crawford, and then shortly after I started my own blog The Daily Mathematics. I would just write stories about my adventures with Diddy and Jay-Z and Damon Dash and Russell Simmons. And unbeknownst to me, I’m just writing and throwing these stories into this bottomless pit. But it starts resonating online, particularly with the hip-hop bloggers and with the hip hop audience. Then my blog became a thing, and Combat Jack became a name. So about after three or four years of writing, I got approached to host my own online radio show. I held off for about a year because that definitely was not my thing. Like ’05 to ’09 was kind of this golden age with regard to hip-hop blogs, and I felt that age was kind of dying off. I was like, “Listen, I have nothing to lose. I don’t have an audience. I mean just try it.” So I started the Combat Jack Show on a whim in August of 2010. And then I found out that I liked it, you know? It wasn’t initially like an interview show as much as it was me and my gang. Dallas Penn was my co-host. We would just talk;we just sit around and talk, caca all night. You know what I mean? And this thing started catching a buzz, we started getting interviews. Our first guest was the late, great, Sean Price. And then Just Blaze, The Premiers, EPMDs, the Redman’s–the caliber of our guests really just started improving, and then it became my career. So it was like about a year and a half after I started doing this online radio thing, and we had since been putting recordings on iTunes podcast. I didn’t even know what the hell a podcast was until like a year and a half after I started this thing, Jesse. So it was all fortuitous. That’s been the story of my life.I’ve been this wanderer. I don’t have a plan, I’ll fall into it. It’ll be great. I’ll thrive in it, and then I look for the next thing.

Jesse: When you started the show, what was your model? I heard you reference Howard Stern at one point.

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Reggie: My model was Howard Stern. Like his interviewing skills right now are just, it’s so compelling. His subjects can be somebody that I really don’t give a damn about, and he pulls the most interesting stories out of them. And then I become interested in his subjects. So, Howard Stern was a huge influence on me because I was like, “I want to be able to talk to anybody and make this thing engaging to anyone listening.” Of course, Star and Buc Wild from the Hot 97 heydays. Because those guys are just so irreverent, and we have never seen anything that irreverent in hip-hop before. Also just, going back to the old school days of urban radio and Frankie Crocker on WBLS. He was a master disc jockey. But he also was brave enough to transcend or break through barriers. So like, if say urban radio only played black music, he’d play in a funky Rolling Stones record or Mick Jagger or whatever. And his thing was always, “Let’s break convention.” So those three were my main inspirations with regards to the Combat Jack Show.

Jesse: One of the things that I think is different about your show, but that is similar to what Stern does, is that because you have over 7,000 people in the studio with you at any given time, you can be the dad a little bit, you know? You can be the straight man. You can be the, “I-went-to-Cornell” guy. And at any moment one of the other 22 people co-hosting your show with you can ask a totally impertinent question that you couldn’t necessarily have asked, being a dad.

Reggie: Right.

Jesse: It’s because there’s six people in there, and everybody’s got a voice.

Reggie: Of course. I’ve kind of moved away from that model because now the format really is one-on-one. It really is just the interview. But initially it was definitely capturing that zoo-like atmosphere that Howard became so famous, with regard to crafting his show.
 

BEING AN INSIDER

Jesse: So you lived through these times in hip hop, and it was your life and career. I’m sure there’s a lot that you’d just know about these people. But what did you learn when you started doing interviews? What didn’t you expect?

Reggie: I didn’t expect people to open up to me the way that they do. I think the reason why they do is because they don’t view me as an outsider, or a shock jock that’s trying to find red meat on them. I really want to have a dialogue with these people. And what works in my favor is about 50 to 60 percent of my subjects or my guests, I’ve had experience with them in the music industry. Some of these guys, at least 20 percent of them, were my former clients. So we had the same type of conversations 20 years ago that we’re having now. These private, real, intimate conversations where they’re trusting me with either their business or the issues with regard to their lives–personal stories that they never told anyone. A good attorney is almost like a great therapist, and I kind of envision my show as being therapy for my guests.

A good attorney is almost like a great therapist, and I kind of envision my show as being therapy for my guests.

A WIDER AUDIENCE

Jesse: Do you think of yourself as making your show for people who are hip-hop heads?

Reggie: No. I make my show for people that are interested in hearing a great story, and once again this is the aspect of Stern that I copy. I don’t know who Stern designs his show to be listened to. But everyone listens to Stern, like from every segment of Americana. You know what I mean? And even if you don’t give a shit about hip hop, if you hear an amazing story you’ll be captivated. I find that a lot of my audience, now that I’m kind of experiencing this burst in terms of listenership, come from everywhere, Jesse. It’s the story, man.

Jesse: Do you feel like part of your responsibility as the host is to give some context for understanding for those stories?

Reggie: No, I leave that to my audience. I’m working on a new project right now with Gimlet and Spotify called Mogul: The Life and Death of Chris Lighty. It’s a six-episode series on the life and death of Chris Lighty, who is the super famous, super successful executive in the music industry. And then four years ago, he died, and it was ruled a suicide. But I find working with Gimlet that I do have to create context for a wider audience. And that’s something new that I’m learning right now. But for the Combat Jack Show, you jump in it.

Jesse: I’m sorry, Reggie. You said you have to create a context for a “whiter” audience?

Reggie: Wider. W-I-D-E-R. [Laughs] But yes, actually, a wider audience.

 

ASKING UNCOMFORTABLE QUESTIONS

Jesse: What is the thing that you’re nervous to ask about? What’s the thing that you’re uncomfortable asking about?

Reggie: I’m usually nervous about the salacious questions like, “Hey you were blasting your wife last week on Instagram or your ex-wife.” Or, “Hey did this…” You know the questions that our most beloved shock jocks jump into. Those are the ones that I’m very nervous about asking because that’s not my show and that’s not the type of person I am. I’m not trying to find that “Ah-ha” moment. I’m not looking for the red meat. I’m looking for the heart and soul, not the the stuff that everybody runs to. I’m not looking for the headline. I feel it’s kind of insulting and disrespectful for someone to trust me, and then I go into those moments now. Sometimes I have to because sometimes those stories or those incidents in their lives are part of what makes them who they are. But I always feel uncomfortable about going towards those very personal, embarrassing moments in someone’s career. But sometimes I have to, you know what I mean?

Jesse: What was a time that you felt like you had to ask something that you were uncomfortable asking?

Reggie: DJ Mister Cee. Who was a legendary DJ, who was a DJ for Big Daddy Kane, discovered Jay-Z, discovered the Notorious B.I.G. A couple of years ago, he makes headlines, busted for soliciting on the street a transsexual. And then it happened again. It was just a big dramatic moment in New York hip hop radio where he was being interviewed on-air and he’s crying. It was just so painful. I got him to be a guest, and I talked about the legendary era, Big Daddy Kane’s era, what is it like mentoring a young Jay-Z, and what is it like discovering a young Notorious B.I.G. And then, can we talk about this incident. You know? That was the elephant in the room. But fortunately enough for me, Mister Cee knew that’s why he came on the show, and he wanted to come on the show. Because if there was anyone else that he would trust his story with–his story and those incidents in his life–it would be me.

 

STRUCTURING THE INTERVIEW

Reggie: The blueprint is the narrative of someone’s life. But 9 out of 10, we get caught up in the waves of what’s going on currently in current issues. I mean, it’s almost impossible right now to stick to the script with regards to someone’s life in this political climate that we’re living in. So I find a lot of my interviews of late shift from, “What’s your story?” to like, “What’s your views?” and “What do you feel about this current administration?” Black Lives Matter has been such an important theme over the past three or four years on my show. Or just “What’s going on with the North Dakota pipeline?” And so I find a lot of fodder for my interviews to be based on what’s happening currently and how that affects my guest’s individual life. So it varies, you know? It’s very difficult to stick to the script when we live in such amazingly interesting times.

 

HIP HOP & JOURNALISM

Jesse: What in mainstream journalism about hip hop makes you cringe? When there’s a story about hip hop on on 60 Minutes or in the New York Post or whatever?

Reggie: I would say more like the Pitchforks and the Noiseys. I would say when it really does feel like the interviewer is someone that’s on safari.

Jesse: Right.

Reggie: And case in point–what is this guy’s name from Chicago? Crazy thugged out rapper, where this guy had warrants, and he had a troubled past?

Jesse: You talking about Chief Keef?

Reggie: Chief Keef. They got him on camera, like smoking weed. I think even like brandished a gun or something like that, and it led to his re-incarceration. But it was really because this guy is a spectacle, and let’s just hype up every aspect of his life that’s a spectacle for clicks. I just think that kind of culture vulture, that kind of like journalists on safari aspect. It makes me cringe. Because my thing is like, “Well, Chief Keef. What are some of your issues? And you’ve been shot and what led to that?” I’m trying to make them cry, dude. I’m trying to be the rap Oprah.

I’m trying to make them cry, dude. I’m trying to be the rap Oprah.

Jesse: I don’t remember the demographic numbers for NPR exactly but like a big chunk of my audience is old, white people. And so the question for me is, especially as a guy who is so audibly and apparently a white coastal elitist, how do I include those people [hip-hop artists] without being an anthropologist? Without presenting what I’m doing as though I’ve just returned from some foreign shore?

Reggie: I’m fortunate that being of the culture, and based on my base listenership, I don’t have to worry about that. And so I’m able to just jump into the meat of the real issues and real questions. I don’t have to explain. It’s not arrogance as much as it’s pride in my culture and wanting to protect my culture and wanting to be one of those people of the culture that curates the culture. I don’t give a fuck about those that really don’t understand the culture. Black people have been in this country for 400 years, and it seems as if white America has been studying us for 400 years, and they still don’t get us. So if this were a class in college, a lot of white people will get an F in Humanities 101 man.

 

STAR POWER

Jesse: What is the thing that you wish you knew when you started doing this series seven years ago that you had to learn?

Reggie: I wish I knew back then not to be intimidated by someone’s star quality. Because that would throw me off a lot, in my early days. I mean of course you learn through action and experience. But coming in from that perspective, you’re looking at your subject less as a human and more as a thing. You know you’re looking at them as a star. So you’re asking them the typical star questions, but I wish I knew that then. It’s not really knowing as much as also being comfortable. You know what I mean?

The Turnaround is available on MaximumFun.org. You can also subscribe on Apple Podcasts to get new episodes as they become available.

Photo Courtesy The Combat Jack Show

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The Editors are the staffers of Columbia Journalism Review.