Like many of Baldwin's extracurricular activities, the show is an extension of his social life. Many of the people he interviews are friends, like Michaels and Turner Classic Movies host Robert Osborne, and the show's co-producer is Baldwin's friend and Long Island neighbor Kathleen Russo, the widow of actor and monologist Spalding Gray. Baldwin says his original idea for his NPR podcast was modeled after Howard Stern – not dirty like Stern, but a proper daily morning show, with a bullpen of regular characters, comics, and writers. One character would have been called the Kid, Baldwin tells me. The Kid would have been given a pocketful of cash and gone out all night and done all the things Baldwin was too old to do now, and the next day Baldwin would ask, "So, Kid, what did you do last night?"
Maybe it wouldn't have been such a great show. Still, Baldwin loves radio. He says his goal on Here's the Thing is to get people to talk about the emotional experience behind whatever it is that they do. "I'm always intrigued by that," Baldwin says. Then he adds: "I'm kind of obsessed with it. Like, I could ask you that. 'Do you like doing this? Why?'"
"No, I'm asking you." He's leaning forward again. This is back in the Grand Havana Room. "Do you like doing this?"
I do, I tell him.
"Why?" he asks, sounding deeply skeptical. "What about it do you like? I could be boring the shit out of you right now. What do you do when you're talking with someone and they completely disappoint you and bore the shit out of you?"
"Occasionally that happens," I say. "But most of the time, what I like about journalism is that it allows me to dip into other worlds."
Now Baldwin looks appalled. "How the fuck are you dipping into another world talking to me?"
I glance around this private club for millionaires, and then out the window at a panoramic view of the penthouse suites of Midtown. But I don't comment on that. Instead, I say, "Well, I'm finding out about your life."
Baldwin finds this very funny. "So, are there some really, really intense questions you want to ask me, that we should just leapfrog to right now?" he asks. "Let's get to the granular stuff. Forget about things you can just get on IMDb and Wikipedia." "Of course," I say, slightly offended. "I'm trying to avoid tha–"
"C'mon. Lay it on me. Let's have a real tête-à-tête here."
"Well," I begin slowly, blatantly stalling for time, "the evolution of your film career is one thing that interested me."
"Go even further," Baldwin interrupts. "What do you mean by evolution? Spit it out."
"Well, moving from the period where you could have become Bruce Willis, let's say," I begin. I'm referring to that point, earlier in Baldwin's career, when he played Jack Ryan in The Hunt for Red October, which was shaping up to be one of the most sought-after franchises of the decade – this was 1990 – and then, somehow, Baldwin ended up being replaced in the sequels by Harrison Ford. I'm trying to be diplomatic. "So, you went from almost becoming Bruce Willis to . . . not doing that. And that not happening for, uh, whatever variety of reasons."
"So what's the question?" Baldwin says.
"The question is," I begin. But I still don't really have a proper question. I say, "Looking back from where you are now, do you ever want to reclaim that past in some way?"
"It's too late to reclaim it," Baldwin says dismissively.
"Yeah, obviously you can't go back in time," I say, warming up to my weird nonquestion. "But now you're loved for all of these comedic roles. Rightly so, I think. But are you content to keep going in that direction, or do you ever want to get back to something–"
At this point, Baldwin interrupts me again and tells a very long story.