Do you enjoy challenges? Then you should try going to sleep before you have to interview Marc Maron the next morning.

It’s not that Maron is a scary or intimidating star (though he is known to be cantankerous); you’re staying up because you know you’re going to be talking to a man so good at conversing that he elevated an entire medium, the podcast, into the eyesight of popular culture.* And you’re doing it on the day he releases the 600th episode of his long-running podcast, WTF with Marc Maron, which inspired thousands of people to buy recording setups and start interview shows of their own.

Luckily, I’ve listened to Maron since he was on episode 16 of WTF, back in 2009. Like many of his listeners, I feel like I know him, so it was easy to think of questions. And he was also just like he is on the show: honest, quick-witted, and a little bit volatile. He even went on a bit of a rant when I asked about his issues with his neighborhood pizza joint. (I’m posting it below, complete with my breathing, because it’s such a great Maron moment that I can’t keep it to myself.)**

On the phone from New York, Maron talked about his show Sunday at Davies Symphony Hall, the new interview show he’s developing for Vice’s new cable channel, and exactly how he gets such great interviews.

What is going on with the Vice show?

I just did a deal with them. Vice is starting an entire network, though it has yet to be announced where that network is going to be. I was approached by Spike Jonze, Lance Bangs and a couple of the Vice guys to see if we could come up with a show that would engage my interviewing skills or my conversational skills. We came up with a format that will honor what I do: longish-form interviews that happen out in the world, hopefully in environments that are emotionally charged for the interviewee, or somewhere that makes them a little awkward — though I’m not planning on going into their homes, if I can help it. I’m not trying to make a lifestyle show.

Each episode is going to be like a documentary about an interview. People are going to follow my process a little bit as I move towards it.

Your interviewing style is uniquely yours, but in the past you’ve talked about how a producer helped you hone your skills while at Air America. Was that Brendan McDonald, the current producer of WTF? Was he with you from the beginning?

Yeah, he was there the day I walked in. He was an associate producer on my show (The Marc Maron Show) and he was a kid; I think he was 24 when I met him. Maybe.

He’s been with me the whole time, through all my radio projects and my video project with Sam (Seder) as well. I’ve been with Brendan for a decade.

How did he help you when you were first developing your interview skills?

When I got to Air America, I got on the mic, and you are either going to connect with that kind of mic or you’re not. I don’t know what makes people more appealing in audio as far as their skill set goes. It’s some kind of weird gift. It’s something that anybody can do, but in order to pop on that mic, who knows what that is. I know I enjoyed it, and once I learned how to man a mic solo, I transitioned that into something that could be very creative and expressive and immediate for me.

In terms of interviewing, when I was doing politics at Air America, there was a lot of stuff I didn’t know and didn’t understand. I needed it to be contextualized, so Brendan, who is the smartest guy I know and understands me, put things that were fairly large or broad and complicated into context for me so I could talk about it efficiently. In terms of WTF, on his part, I don’t need him to do research for me, unless I really don’t know or have time. I don’t do a lot of research anyway, but when we have something specific we need to cover, I’ll always talk with him about where to go with that. But generally I’m on my own. At this point, Brendan does most of the engaging with the outside world and all of the production. He also handles all of the booking, the advertisers… He is the business side of it and the production side of it. I basically talk to people and send him the files, and he makes it a masterpiece.

For you, what is the basic foundation of a good interview? What are you always trying to go for?

I don’t know if I ever set out to get anything. I don’t call myself a journalist or even an interviewer — generally when I talk to Brendan about an episode, I ask him, “Was it a good talk?” or “How was that talk?” To me it’s still a conversation and that’s really what I’m aiming for. I have places I want to go, and I will usually find an area that I think is rich and could reveal more about the person. I’ll have that in my head once I’ve educated myself a little bit and have an overview of the person — my projection of who they are, where they came from and what their lives look like.

With that portrait in my head, I engage them on what I think, and most of the time I’m wrong. But I really seek a connection and a nice, full conversation.

You have said on your show a few times that you don’t prepare, but it seems like you are preparing for these talks. Also, for your interviews with musicians, like with Kim Gordon, you will listen to their records before speaking to them.

I prepare in a very broad way. Maybe I just underestimate what preparation really is? What I really don’t do is prepare questions. Hardly ever. I’ll make an outline of subjects and put that on a piece of paper in a very scattered way, almost like fragmented thoughts along with bits and pieces of their lives as reminders. It’s like with my standup — I have a hope that somewhere these things will be mentioned or covered sufficiently in the course of the conversation. It’s almost like I sketch moments and ideas that I hope to get in there somehow. It’s a way to prime my brain.

So you’re really not just winging it. And in reality I bet people think they could just wing it, but that’s not what you’re doing at all.

No. I wing it more in the garage. But I am in New York and I interviewed David Byrne the other day. Musicians are a little more difficult because you’re talking about an artist that remains very productive, usually for decades. Most of them, whether you know it or not, continue to produce a lot of stuff and go through a lot of different things. I was really honored to talk to Byrne; I love that guy and [Talking Heads] were a very important band to me, so I had a big sheet when I talked with him.

But a lot of times in the garage I don’t have much, and I take notes as I talk to people to make sure I come back around. Like last night I interviewed Terry Gross live at the Brooklyn Opera House, and I had a pretty good-sized sheet, but there’s so little available on her that the talk was going to be what it was going to be. But I did know there was an area that I saw nothing on, and it struck me as a fairly rich area of conversation. And it turned out to be that I was right.

Knowing how big of a music fan you are, if given the opportunity, would you interview Ted Nugent?

The weird thing with guys like Ted Nugent is that whatever they were known for overshadows whatever you want to talk about. I think it would be impossible to talk to him specifically about music without discussing his current agenda — which I have issues with — and I’d have to indulge his point of view. It seems impossible not to argue with him. If I could have a conversation with him about Detroit and the Amboy Dukes and moving up through the ’80s without it becoming politically charged and forcing me to defend what I believe… I just don’t know if it’s possible anymore to do that with him.

Look, for one reason or another, when I was in high school, I ended up seeing Nugent three times. He was definitely a force and a unique individual, but now, I don’t know. Politics corrupts everything.

*Though Serial brought in record numbers of new podcast listeners, WTF was the medium’s flagship for a long time, especially because it wasn’t already a radio show.

**Thanks to Town Pizza employee Jed Maheu for the tip.