July 9, 2024

The Singular Fredness of Armisen

Fred Armisen grew up idolizing trailblazing musicians, from The Beatles to The Clash and The Talking Heads. But spending his twenties drumming in bands never seemed to land him further than moderate crowds and endless nights loading his gear into the van. In need of a change, he turned to comedy, honing the craft of creating characters we know and love him for, on shows like SNL and Portlandia. I connected with Fred while we were both on set in different locales to discuss his unusual pivot, why he still feels an intense yearning for the music he loves, and the strange intimacy of filming a fight scene.

July 2, 2024

Check it Out: “Kierkegaard or Californication? (with David Duchovny)”

This week I wanted to share this interview I did with my friend Samantha Bee on her show Choice Words. Read more about our discussion below, and happy listening. We’ll be back next week.

June 25, 2024

Tony Hawk and the Trick That Changed Everything

I may not know a lot about skateboarding, but I can recognize the type of relentless drive that fuels Tony Hawk. He’s left his mark on a sport that thrives on risk, which means he’s soared high and fallen hard. On the 25th anniversary of Tony landing the first “900” — a trick where he somehow spins 900 degrees in mid-air — we discuss the years of trial and error (and the broken rib) that led to that fateful moment. I also inquire about what’s kept Tony on the board all these years, and what lessons he’s applied to life off of it.

June 18, 2024

Sean Penn and the Squared-Away Individual

There are few actors left who embody the ethos of old Hollywood. Sean Penn is one of them. We got together at his place for a face-to-face exploration of Sean’s life and career. We discussed how his childhood in Malibu helped him create the iconic Jeff Spicoli, and how his first acting coach still shapes him today. We speak of his friends — Brando, DeNiro, and Scorsese — legends whose reputations, work ethic, and willingness to keep learning shaped their characters and their lives. Spending an hour in his presence is a masterclass in the pursuit of being a better creator, and a better human.

June 11, 2024

Patric Gagne and the Art of Sociopathic Zen

When I first heard about Patric Gagne, a diagnosed sociopath with a buzzy new memoir, I was intrigued. If she lives without the social emotions that often hold us back — embarrassment, jealousy, and shame — does she actually have a superpower? What can she teach us about failure, and does she fear it like the rest of us do? After tearing through her book, I sat down to discuss these big questions, bust the tired tropes, and learn about the Zen of sociopathy.

June 4, 2024

Stephen Dubner and the Joy of Quitting

Stephen Dubner, host of Freakonomics Radio, has done more than change the way we think about economics — I consider him a spiritual guide of our time. But for all his success, he’s got a laundry list of careers he’s left behind, from rising-star musician to New York Times writer. We debate the merits of expecting the worst versus hoping for the best and discuss how to trade nuance for novelty as we get older. It’s never too late to keep learning — or, according to him, to start a podcast.

May 28, 2024

Sarah Silverman and the Stupid, Shitty Things You’ve Done

On stage and off, Sarah Silverman is always evolving, whether that’s honing her standup routines or coming to grips with missteps in her past material. We reminisce about our mutual friend Garry Shandling, including the comedy star-studded basketball games he used to host, where I first met Sarah. I also have the pleasure of talking to Sarah about the satisfaction of apologies and the struggle of forgiveness, and I realize, once again, that I extend much more grace to others than I do to myself. Lucky for me, Sarah won’t stand for that.

May 21, 2024

Brad Gilbert and the Problem with Perfection

Like all of us, athletes fail often. Renowned tennis coach Brad Gilbert knows that well, and has spent decades analyzing weaknesses as a way to develop strengths. As a player, he rose to the rank of #4 in the world, then began coaching stars like Andy Roddick, Andy Murray, and, most recently, Coco Gauff. He even trained Zendaya for the movie Challengers. I loved hearing how the man Andre Agassi called “the greatest coach of all time” gets even more out of the best players in the game.

May 14, 2024

Gabor Maté and the Reason We’re All Addicted

This is my most personal episode so far, but it’s really about the wisdom of Dr. Gabor Maté. The author, physician, and public speaker reminds us all how we sometimes become too comfortable with self-criticism and regret. We talk about parenting, collaboration, and addiction, and I leave the interview feeling a level of gratitude that I don’t know what to do with. Here’s that conversation.

May 11, 2024

EXCLUSIVE PEEK: Reflections on Bette Midler

You can get even more Fail Better with Lemonada Premium, where I share the extended thoughts I have after each interview. Here’s a free peek at what you could be getting: After my conversation with Bette Midler, there are many things I’m still wondering about because I couldn’t find a way to bring them up, including what I wished I’d asked her about parenting. Subscribe to Lemonada Premium now in Apple Podcasts.