'It’s working if it makes me nervous'

American-Canadian humorist Jonathan Goldstein joins his guests for awkward reunions and nerve-racking conversations as they try to get closure

Week 31 Podcasts Jonathan Goldstein

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“My barometer for knowing it’s working is that it makes me nervous. I feel scared.” Jonathan Goldstein is describing the moment in his podcast Heavyweight that millions of listeners have come to know so well. It’s the time of denouement, usually around two thirds of the way through each episode, when his guest, having arrived with a long-held regret, unexpressed desire or occasionally a grudge, faces their reckoning. No matter who it’s with, be it a distant relative, an estranged friend, a significant teacher or a lost love, the stakes are always high.

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Heavyweight, which debuted in 2016, was inspired by various ideas Goldstein developed as a producer on the non-fiction US public radio behemoth This American Life. “The stories I cared about seemed to share a common denominator of deep dives into the past with an element of regret,” he remembers. “One of them was even called The Things I Should Have Said.”

This elegiac quality was present in Heavyweight from the very first episode, which featured Goldstein’s attempts to heal a decades-old rift between his father and his uncle. As the two pensioners finally met after 40 years’ silence, the tension was palpable. “My boss, Alex, had always wanted to put me in situations where I was uncomfortable,” Goldstein laughs. “I felt that I stood a strong chance of making this situation worse, but I was also deeply invested in the outcome.”

Another early episode featured his friend Gregor, who once loaned the pop star Moby a box of CDs that inspired the 1999 hit album Play and now wanted them back. Goldstein’s encounter with the bemused millionaire musician is priceless. More recently, a two-parter about a broken family was both surprising and profoundly moving.

Throughout, Goldstein’s winning combination of comic awkwardness and compassion are key to the show’s success. He remembers how, following a first season filled with family and friends, strangers began writing in with their requests for help. “The look of hope on their faces was daunting. I felt like maybe I’d bitten off more than I could chew, that they thought I was an expert in this area that I’d just invented. They were strangers, but I grew to care about them too, so that was very rewarding.”

Despite millions of downloads and being a rare podcast that has made money, the show was dropped by its original platform after eight seasons in 2023 – “I guess our long-lead documentaries no longer fit their business model; the investment’s quite heavy,” says Goldstein philosophically – but will return in a new home on 18 September. The break has made the presenter more appreciative of both what Heavyweight brings to the world – a quiet, constant celebration of solidarity between folk – and his part in it.

“Our stories never go the way we want them to, and I’ve come to realise that it’s maybe for the better,” he reflects. “We all have failed friendships, things left unsaid, and we pretend they don’t matter. This is the opposite of that, it’s the search for meaning and permission to say, yes, something matters. This is what we’re alive for – relationships and connection.”

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Has presenting the show changed him? “My sense of confidence has deepened, even if it’s to show that I still don’t know what I’m doing, and that’s OK. I don’t know if this is because I’m going soft in the head or it’s a function of age, but I’m finding myself more easily moved.”

Authors

Caroline Frost

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