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Josh Gondelman, aka 'The Nicest Guy in Comedy,' joins us this week to explore the true essence of kindness, when being nice can actually backfire, and how 'niceness' differs from 'goodness.' Josh is a Peabody- and Emmy-winning comedy writer, known for his work on Last Week Tonight with John Oliver, and currently serves as a senior staff writer and producer on the Showtime series Desus & Mero. He also released a stand-up album, 'Dancing on a Weeknight,' and authored a new book titled 'Nice Try: Stories of Best Intentions and Mixed Results.'
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Episode Highlights
Insights from the Josh Gondelman Interview
On being labeled 'The Nicest Guy in Comedy':
Part of it is that people just don’t buy it when I’m mean on stage. It feels off-brand with my usual tone and personality... I’ve tried little experiments, like, 'Oh, I’ve seen others do this,' but it never feels genuine or authentic to what I want to express. It’s like trying to be something I'm not—it never clicked. I never had a phase where I wore a leather jacket, smoked on stage, and told dirty nursery rhymes or anything like that.
On distinguishing between 'nice' and 'helpful':
I often think about the difference between niceness and goodness. Niceness is about being pleasant, polite, and agreeable. It's about creating a conflict-free space with someone. These are valuable qualities in many situations. But goodness is more about doing what’s uncomfortable but ultimately beneficial—whether that’s being generous or standing up for what’s right. They overlap sometimes. For instance, giving a loved one a birthday gift is both nice and good. But if someone asks for advice on something, and you tell them it’s a great idea when it’s actually not, that’s nice, but it’s not good.
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