Uncomfortable Conversations with Josh Szeps

Noam Dworman is the owner of comedy’s most revered venue, the Comedy Cellar, sometimes referred to as the "Harvard” of comedy clubs. He transformed it from a single 1980s room in Greenwich Village into a five-venue behemoth.
The stars who made their name on Dworman’s stage are a who’s who: Richard Pryor, Steve Martin, Chris Rock, Jon Stewart, Amy Schumer, Ray Romano, Sarah Silverman, Dave Chappelle, Louis C.K.
Why does Noam still do it? What has he learned about how to lead a good life? Is it harder to get ahead as a small business owner these days? And why is he getting fined for other people’s sidewalk trash?
Josh visits Noam at his studio above the Cellar to discuss how to give the benefit of the doubt to people who are wrong—from border-town voters, to Trump officials. They wrestle with free speech, ICE, bureaucracy, and why cancel culture’s “consequences” might be harsher than we think.

As we hold our breath to find out whether Israelis will finally spurn Netanyahuism, Yael Bar Tur joins Josh to definitely NOT discuss the Israeli election.
Yael majored in counterterrorism in Israel and has a master’s in public policy from the Harvard Kennedy School of Government. As the NYPD’s head of digital, she was on the front lines of the official response to the defund-the-police movement of the 2010s.
Josh and Yael dug into the Israeli electoral system, the American banking system, policing, and, randomly but inevitably, the new documentary about Elizabeth Holmes.

This episode is part of The Best Of series and was originally posted in 2024.
Few Britons are as iconic as Stephen Fry.
On TV, he’s an Emmy-winning comedy legend immortalised in shows like A Bit of Fry & Laurie, Jeeves & Wooster, and Blackadder. He has hosted the British Academy Film Awards twelve times and won six BAFTAs as the host of the smash-hit BBC television quiz show Q.I.
On stage, Stephen’s adaptation of Me and My Girl won two Olivier Awards. He was nominated for a Tony for his performance in The Globe’s production of Twelfth Night on Broadway.
On the big screen, he’s starred in Wilde (as Oscar Wilde, a performance nominated for a Golden Globe), Gosford Park, Chariots of Fire, A Fish Called Wanda, V for Vendetta and The Hobbit.
Stephen is the voice of all the Harry Potter audiobooks. His eloquence infuses his countless essays, comedy sketches, articles, novels, and books about Greek mythology.
His autobiography, Moab is My Washpot, with its raw honesty about his screwed-up teenage years, was transformational for a young Josh Szeps.
On a trip to Sydney, Stephen swung by the Uncomfortable Conversations studios to visit with Josh. Enjoy this sparkling conversation about the cycle of life, the richness of being human, finding creative authenticity, and ignoring Donald Trump.

Is the exhausted majority stuck choosing between two extremes that can’t be satisfied, and what happens when the far left and far right go head to head?
Josh chats with comedy writer and author of I Might Be Wrong, Jeff Maurer, live from a Washington, DC, hotel room, about why centrists keep losing the argument on both sides. They dig into the chaos in France, where a nation that riots over a modest rise in the retirement age may now face a runoff between an old-school communist and Marine Le Pen, and why Jeff thinks the far right wins that contest almost every time. They also cover the motte-and-bailey fallacy, Australia’s superannuation fix versus America’s looming Social Security cliff, why the left needs its own “Nixon goes to China” moment, the illiberal turn in progressive race politics, and the case for a really basic version of Medicare for All.

Is it more ethical to prosecute your moral beliefs, or to understand people who disagree? Who, exactly, is fomenting polarisation? Who is capable, potentially, of political violence?
Is it, perhaps, all of us? Especially those of us convinced we’re doing good?
Several months ago, Josh hosted an Uncomfortable Conversations panel event at a black-tie gala in the nation’s capital with the federal member of parliament Helen Haines. This week, Haines was intentionally rammed by a car. She has lost both her legs.
The prime minister is trying to soothe a shocked nation by encouraging “people in positions [of influence]… to join in the call to turn [the] temperature down.”
Josh knows a thing or two about fostering conversations across ideological divides. In this ad-libbed editorial from New York, Josh argues that telling other people to turn the temperature down is worse than useless.
Nobody thinks their own temperature is set too high. Rather, we believe that less passionate people are feckless or corrupt.
This points a way forward, towards how we all might participate in creating a more cohesive society.
Our thoughts are with Helen, her family and her loved ones. We hope that in some tiny way, this helps.