Jonathan Goldstein of Heavyweight on Playing Out the Past in the Present

The Heavyweight host reveals how he helps people deal with things in their past that they wish they could change.

Four years ago, Alex Blumberg, CEO of Gimlet Media, got together with Jonathan Goldstein to discuss creating a new show with him. Goldstein was a long-time contributor and producer on This American Life, and for 11 years he hosted the popular Canadian radio show WireTap in the wry, droll manner that has become his trademark.

“Alex basically liked the idea of placing me in uncomfortable situations,” says Goldstein. “He thought that was where I’d be at my most interesting. At one point the idea was floated that he would send me to the airport in New York with a sealed envelope that I could only open once I was there and it would tell me where I was going and what my assignment would be. That amused him.”

In the end, they came up with Heavyweight, which debuted in 2016 and will enter its fourth season later in 2019. In the show, Goldstein takes people back to a time in their lives they wish they could change – sometimes it’s something they did; sometimes it’s something they didn’t do; often it’s something they regret or don’t understand. One thing they all have in common is that they want answers and a chance to do things over again.

Goldstein is there to guide them through this process – Rachael had a baby ten years ago but never informed the father; Jesse wants to reconnect with the stranger who ran him over and nearly killed him to thank him for changing his life; Gregor wants to ask Moby why he never returned the CDs he borrowed that became the basis for the album that transformed him from washed-up musician to millionaire megastar. The host has also revisited an experience from the past, most notably in episodes about meeting up with the first girlfriend who broke his heart, and finding the non-Jewish boy he once met who went on to become a Rabbi just as Goldstein was losing his faith. We caught with Goldstein about how those experiences plus others went over.

Spotify for Podcasts: When someone finds out you’re a podcaster and asks you to you describe Heavyweight, what do you say?

Jonathan Goldstein: Well, first of all, I become embarrassed because doing a podcast somehow doesn’t seem like a real vocation. I was recently called in for jury duty and the bailiff went through each of the potential jurors and you give your name and address and your job. I was filled with anxiety as my time was coming and I would have to say I was a podcaster. But before they got to me, one of the other jurors had the same answer. It took me a while to arrive at something quite simple to describe Heavyweight, which is this: it’s a show in which, together, I and a subject go back to a particular moment that they want to fix or undo that’s had negative resonance in their lives. It’s like therapy, but therapy as a real-world quest where we go an adventure rather than lie down on the couch.

Many of the people you feature on Heavyweight are dealing with confusion or disappointments or difficult moments in their lives. Yet you manage to bring a lot of humor to the show. Is that a difficult balancing act?

It is a constant conversation and a constant concern getting that balance right. Often times I’ll play versions of things to my wife and she doesn’t like my digressive flights of fancy as much as I do. I think when they get in the way of the story then it’s a problem. But when it has that chiaroscuro effect of making the dark parts darker and the light parts lighter, then that’s the most gratifying. I don’t want to make light of someone’s pain. That’s why it’s easier to make stories about myself because I can self-deprecate at will.

Yes, in the first season of Heavyweight you primarily used yourself, your family and your friends for stories. Then in the second season, you looked for other people. Did that make it more difficult? And did you source those stories from listeners?

Yes, they largely came from listeners sending in ideas, and yes, it was very daunting. You’re right, when I conceived the show it was something quite personal and soaked in my own life and the lives of the people I knew, so the second season was something of a reinvention. It ended up being really gratifying. It allowed me to get out of my own head and to think and care about other people.

Are there certain elements you need in order to make a Heavyweight episode fly?

We do start a lot of things that don’t come to fruition. Everything can be in place – an interesting subject, the stakes are there, but people might not want to talk. The elements I do want to see are intensity and vulnerability and an ability for someone to put themselves in the skin of the person they once were, without detachment. You don’t have to be the greatest talker in the world or the most psychologically astute person, but people relate to vulnerability and the sincerity of the quest. The other thing is that I like to feel I can actually do some good. If it’s just an interesting hole to go down with interesting characters but there’s no point, then whey go down there? I like to come out the other end and at the very least be able to say that I didn’t make a person’s life worse.

With that in mind, are there particular episodes that have had that extra resonance, where you felt that you really helped someone get closure or answers?

Yeah, they’re the ones where the endings were bittersweet, where it’s not the rosy ending the subject was hoping for, but it felt as though a greater truth was gotten at in a way you could feel. The episode about Moby with my friend Gregor – in the end it felt like Gregor wasn’t looking for fame or riches or credit, he just wanted to hang out with his old friend Moby and feel that Moby was glad to see him. And I felt that. They were both funny and hyper-intelligent and kindred spirits. Being in the room with them you could feel that. The other one that comes to mind is the episode called Christina, about the girl who always wanted to play basketball, but her foster mother made her quit. I was worried whether people would think we were verging on self-parody because of its smallness, but even though it was small it always felt real and never petty or manufactured. At the end, she connects with her foster mother and there are moments when they realize they’re more similar than either of them would have anticipated. It’s not a happy ending because her stepmother is a tough old bird who is not sentimental and doesn’t want to admit regret. But what she’s able to offer Christina is the truth and Christina is able to appreciate her for what she is.

—Barry Divola