Heavyweight’s Jonathan Goldstein in the Hot Seat
By: Skye Pillsbury
Tags: Podcasting, Spotify, Gimlet Media, Podcast, Interview

Heavyweight’s Jonathan Goldstein in the Hot Seat

It’s 2017 and I’m sitting in my car, listening to the Heavyweight season two finale. In its final moments, the host mentions that the show is looking for stories. If I’m being honest, I’ve been waiting for this moment. I have a story. And most motivating of all, my kids want me to pursue it. In seemingly slow motion, I take out my laptop and pound out a pitch, hit the “send” button. I feel sure I won’t hear back, and the receipt of an auto-reply seems to confirm my hunch. I feel secretly relieved— but not for long. Within 24 hours I’m on the phone with Heavyweight producer Kalila Holt and a beautiful and terrifying journey has begun.

That’s the origin story of episode #17, “Skye.” The premise of Heavyweight is simple: host Jonathan Goldstein eases friends and listeners, and sometimes himself, into revisiting and redeeming regrets. In its most well-known installment, Goldstein attempts to get a friend’s CD set back from electronica musician Moby; in another he brokers a meeting between a permanently disabled man and the driver who caused his injuries. In every scenario, Goldstein’s able to strike the perfect emotional tone while imbuing each story with humor and whimsy.

Earlier this year, I sat down with Jonathan to ask him all the questions I had stored away while he (and his team of producers) created “Skye.”

This interview has been edited for clarity and length.

How did you develop the idea for Heavyweight?

We tried all kinds of things. Alex [Blumberg, founder of Gimlet Media] thought it could be about anything — like we could call it Jonathan Goldstein Walks into Buildings, where I wander into interesting buildings to see what’s going on inside. That probably wouldn’t have been that great of a show. Another idea was to call it Jonathan Goldstein, Medicine Woman where I try to cure the ills of people. At one point we bandied about the idea of sending me to the airport with a sealed envelope containing my destination and mission.

That sounds glamorous.

No — not glamorous — Alex wanted to put me in uncomfortable situations. That’s where he thinks I flourish. If he could, I think Alex would parachute me naked into a jungle, wearing nothing but recording equipment.

In the end, it was like one of those Hasidic tales where you try all kinds of different things, and they end up leading back to the simplest thing that was there all along. I had this one story in my head about how my father and his brother hadn’t spoken in forty years. And from that one story, the show started to take shape. After season one the trick was to see if I could transfer the premise and make it work with people I didn’t know.

And was that because you felt like you had exhausted your own stories?

That was part of it. I didn’t have high hopes for it working because the best episodes of the show tended to be personal — almost hyper-personal. But then it ended up being really rewarding and allowed me to be surprised and form new connections and care about other people. Like in your case, the mention of your son caught my eye. There was something instantly relatable about the idea that you had to do this thing for your child.

[In my pitch to Heavyweight I explained that when I was twelve, four girlfriends had come to my house in the middle of the night and written “F**K YOU” on our garage doors. I never spoke to those girls again. My eleven-year-old son Clark had encouraged me to find out why they did it. “I’ll never have the courage to do this on my own. Perhaps Jonathan can help,” read my note.]

When did you know that my story would become an episode?

The decisive thing was that you and Clark had a really nice rapport. All our stories up until that point were about one person who wanted to do something. Your story was made richer and more complex by the connection to your son. The listener hears the story through your ears — but they also hear it through Clark’s ears; they hear how Clark interprets it. That gave the story stakes.

We also loved talking to your mom. We were charmed by so much of what she said. We asked her how she became a poet and what her relationship was like with her mom. She read us this poem that she wrote about watching you sleep, when you were a baby — it was beautiful. We really liked being able to incorporate all three generations.

There was also something about the atmosphere of your episode that we all fell in love with. [Producer Jorge Just] became very protective of carving out a space in the midst of it that had this dreamy, late-at-night feeling.

Did anything surprise you during the making of the episode?

Before I set out to California, Alex said I should find a studio where Clark and I could watch you talking to your old friend Tessa. I thought that that would be insanity — a formula for complete weirdness. But it worked out. It’s still hard to believe that it worked out as well as it did.

And then — when I left the hatchback door open! I felt bad — but also like, this is great! That’s the safety net of always recording your experience. It’s like, I’m embarrassing myself, but for a purpose.

People asked me if you did that deliberately.

I’m not that much of an evil genius.

Has there ever been a story that you thought would be perfect for the show but didn’t work out?

Many of them. One was about this woman who had never met her father. She’d been told by her mother that he was no good. She went to his funeral as a child and the one thing that she remembered was that there was this guy who was missing two fingers, standing over the casket, crying inconsolably.

So she grows up and has kids and she wants to tell them something good about their grandfather. Her family says don’t bother. But she remembers how this one guy cared enough about her father to cry at his funeral. He must know something that they don’t.

It’s so cinematic — this guy with two fingers, why was he crying?

Somehow we tracked down the guest list to the funeral. And then [producer Kalila Holt] started googling names and finds an insurance claim regarding the wrongful loss of two fingers. It was part of a lawsuit or something. And we’re like — this is our guy!

It was exciting. We’re thinking, all we have to do is call this guy up on the telephone. He’ll say something nice about this woman’s father and — bingo bango, play the theme song — we’re out! But I call him up and he wanted nothing to do with me. And so I call him up again with the woman on the phone — I figured he couldn’t refuse with her on the call. But he just would not play ball — he actually said, “don’t call here again.” We poured a lot of energy into that one.

In the episode “Jeremy” from season one, you mention that at one point you considered becoming a rabbi. Does that same impulse animate Heavyweight?

I’m flattered by that question. Perhaps. The Jews’ relationship with God is one of wrestling. We don’t take things at face value — our questioning is a part of the wrestling. And there’s this idea of showing vulnerability, of letting people live vicariously through your stumbling.

I was just re-listening to S-Town. And I was struck by how much [creator Brian Reed] shows his own vulnerability; it humanizes him. He doesn’t always say the right thing — but he keeps it in the tape, because people relate to that. You can have good writing and clever jokes. But the thing that is the most lasting, the thing that people connect with most is vulnerability.

Are you always pondering these things outside of work — like in your day-to-day life?

Oh yes. With the most personal episodes, the focus is usually about something I can’t get over. It’s a quest for some kind of understanding. I’m at an age where I can now have decades piled up between myself and a troubling experience. If something has stuck around for twenty or thirty years, it says to me that there’s something meaningful to explore there.

We’re taught to look forward or “be in the moment.” But I’ve always felt more comfortable in the past. I remember, as a kid, I was with a friend and I was talking about what a great time we’d had the previous summer. And he said something like, “Jonathan you live in the past.” I was ten years old.

Has the dynamic with people who approach the show with a story idea changed now that you are more known?

When I talk to people, I try to put it out of my head. Like when you and I talked for the first time — maybe it was weird for the first couple of minutes, but it probably gave way pretty quickly, right?

It did. On our first call, I remember saying that I felt a little intimidated. It was just so weird to hear your voice coming out of my phone. But you said something like, “oh don’t worry, that feeling will wear off in five minutes.” It broke the ice.

That’s good to hear. I think I’m more concerned about my own nervousness. Once I’m comfortable, then things are okay.

How did the idea of calling your friend Jackie at the beginning of every episode happen?

It was kind of a last-minute decision to do that. Initially each episode was going to start with me on the Brooklyn G train. I’m kind of dozing off and the recorded voice that usually says, “stand clear of the closing doors” was going to start talking to me about that week’s episode. We produced one intro — but it was almost like producing a whole episode. It was a lot of work. We realized it wasn’t sustainable. So then I just had this thought — let’s call Jackie. It was a last-ditch effort. I played the first one for Alex and he liked it.

People love those calls.

She was in New York a few weeks ago and I went to see her. We were hanging out in the lobby of a hotel and I showed her all the tweets about how much people really enjoy her and think she’s hilarious and find her laugh so infectious — but it really doesn’t mean that much to her. Or so she claims. Maybe she’s just hostile and withholding.

Is there anything you want your listeners to take away from those calls?

I guess that people shouldn’t see me as a voice of authority. I’m just a schmuck who gets hung up on stuff.

If this is the first time you’ve heard of the Heavyweight podcast, get started with “Gregor,” “Jeremy” or “Skye.”

Editor’s Note: “Skye” just received a nomination for Best Audio Documentary from the International Documentary Association (IDA).

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