Terry Gross recently had an interview with Jay-Z that was fascinating. I’ve known that he was articulate and intelligent, but what surprised me in the interview was how insightful he was.

For example, Terry asks him about the effect that crack had on his neighborhood. And what he points out is really interesting, that it fundamentally altered the dynamic of the authority figure. I’ll just quote him:

They have a saying, “It takes a village to raise a child.” It changed the authority figure. Crack cocaine was done so openly, and the people who were addicted to it, the fiends, had very little self-respect. It was so highly addictive that they didn’t care how they obtained it and they carried that out in front of children, who were dealing at the time. So the relationship of that respect, “I have to respect my elders” … that dynamic shifted and it broke forever. It just changed everything from that point on.

That totally makes sense, and I had never thought of that before. Crack destroyed the traditional authority figure. Pretty insightful, Jay-Z. Great interview.

For whatever reason, I listen to a lot of talk nowadays. Here are my favorite interviewers:

  • Terry Gross – probably my favorite. She has the unique ability to draw interesting things out of her interview subjects, like in the Jay-Z interview, and it feels conversational rather than interrogational. Also, of all the interviewers I listen to, she asks the best questions. Her guests frequently prepend their answers by saying “that’s a good question”. They are.
  • Bill Simmons – The Sports Guy is a surprisingly strong interviewer. As with all the other good interviewers, he’s conversational, and draws out interesting answers. Simmons’ unique gift is that he seems utterly comfortable with whoever he’s talking to, be it Cousin Sal or David Stern or Shawn Michaels. It makes you feel like he’s a good buddy (or could be one) with everyone, and that’s really a gift. I think it’s his interview with Michaels that made me realize his talent. Michaels is a WWE wrestler, and not surprisingly, he wasn’t super eloquent and the interview started off stilted and awkward. But Simmons was so relentlessly comfortable and passionate about wrestling that Michaels couldn’t help but be drawn in conversationally. It was masterful.
  • Jim Rome – By far the best short form sports interviewer around. It’s kind of funny, because he’s like the exact opposite of himself in the Chris Everett days; nowadays, his main weakness is that he kisses his guests’ butts too much. But I still think he’s a great interviewer. What I like most is that he seems to actually listen, and he’ll change his line of questioning based on interesting things his guests say, which gives his interviews an element of surprise.
  • Kevin Pollak – What I like: he’s conversational and interested, almost to a fault – his interviews go on for like 2 hours. They’re only occasionally worth being that long (e.g. his interview with Bradley Whitford, in which Whitford revealed that he was raised a Quaker), but in general I like that style. However, he likes to talk about himself a little too much, and he actually ends up repeating a lot of anecdotes.

And my least favorite interviewers:

  • Conan O’Brien – Don’t get me wrong, I love Conan. But I have always found his interviews awkward. I think the primary problem is that his style is intellectual and absurdist. I jive with that, but it makes connecting with guests harder. I actually feel like they’re not connecting a lot of the time, just kind of talking on different levels. Makes me uncomfortable.
  • Dave Davies – He’s a guest host on Fresh Air. The dropoff in quality from Gross to him is insane. What drives me most crazy about him is that it feels like he’s going through a script, not conversing. There’s one little thing he does that I feel exemplifies this – his interviews are filled with him responding with “Right…” It’s the type of thing you say when you want to redirect somewhere, and he says it constantly, almost as if what the guest says is irrelevant. Frustrating to listen to.
  • Ralph Barbieri – For years, my least favorite interviewer. He doesn’t interview. He talks at length, and occasionally leaves his guests brief moments to say something before he interjects again. The Mercury once included a 10 minute transcript of a Barbieri “interview” with Steve Young, in which Barbieri talked so much that Young literally said three words. The man loves to talk. Makes him a great talk show host. But a terrible interviewer. In fact, my least favorite interviewer of all time.

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