Here We Go Again With Kal Penn

Each week, Kal Penn takes today’s trends and headlines and asks: Why does history keep repeating itself? From the new space race and plane delays to fad drugs and movie remakes, our guest's answers will make you feel better about everything.

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Recent Episodes

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Disrupting the Taxi Industry with Bhairavi Desai Tuesday, April 28, 2026

Need a ride? This week, Kal speaks with co-founder, president, and executive director of the New York Taxi Workers Alliance, Bhairavi Desai, about the ongoing disruption of the taxi industry. Bhairavi has fought alongside more than 21,000 drivers to raise the base income, create a cap on the number of ride-sharing vehicles permitted to drive in New York City, and relieve drivers of hundreds of thousands of dollars of debt. But in a new era of ride-sharing and driverless vehicles, what threats remain to cab drives all over?See omnystudio.com/listener for privacy information.

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Digital Shorts with Jorma Taccone Tuesday, April 21, 2026

Short form video is everywhere today. But if you rewind back to 2005, comedy trio The Lonely Island had only just released Saturday Night Live's first digital short: "Lazy Sunday." It went viral, transforming the lives of its members Andy Samberg, Jorma Taccone, and Akiva Schaffer. The Lonely Island would go on to produce hit after hit for SNL, from "I'm On A Boat," to "Dick in a Box." Kal and Jorma sit down to talk about digital shorts, now and then. Plus, hear more about Jorma's new film, Over Your Dead Body.See omnystudio.com/listener for privacy information.

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The Tennis Rally with Andy Roddick Tuesday, April 14, 2026

When COVID told us we all needed to be six feet apart, some people became addicted to TikTok and other people picked up a racket. Since 2019, tennis participation in the U.S. has grown by 54 percent. And that's excluding all the avid pickleball lovers who keep stealing their courts. So, why are we just becoming obsessed with a game that Andy Roddick has been obsessed with his whole life? Kal talks to the former number one player in the world about why and how his sport is making a comeback.See omnystudio.com/listener for privacy information.

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Nithya Raman on running for Mayor of Los Angeles Tuesday, April 7, 2026

LA City Council Member Nithya Raman is running for mayor. On this episode, she joins Kal for a candid conversation. She opens up about how she got into politics, LA's homelessness crisis, and being compared to NYC Mayor Zohran Mamdani. What does being a democratic socialist mean to her? And, what does it take to implement real change in her city?See omnystudio.com/listener for privacy information.

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Spacecraft Failures with Bobak Ferdowsi Tuesday, March 31, 2026

Bobak Ferdowsi is more than just the NASA Mohawk guy. He's a Systems Engineer at the NASA Jet Propulsion Laboratory with an incredible aptitude for studying spacecraft failures so we can learn from them. Kal breaks down Bobak's career through the spacecrafts that defined them, from the Mars Curiosity Rover to a brand new satellite. Plus, why our failures aren't always bad and how to keep the worst ones from happening again.See omnystudio.com/listener for privacy information.

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Distrust in Traditional Media with Mehdi Hasan Tuesday, March 24, 2026

Does anyone completely trust the media landscape anymore? Mehdi Hasan, a broadcaster, journalist, and newly minted CEO & Editor-in-Chief of independent media company Zeteo, has a few insights that might shed light on how we've gotten to where we are, and how distrust has shaped his very specific, highly uncompromising style of reporting.See omnystudio.com/listener for privacy information.

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The De-evolution of Late Night with Bill Carter Tuesday, March 17, 2026

It's been a crazy year for late night TV -- from ratings on the decline and budget cuts to cancellations and political influence. Bill Carter, the journalist and author behind The Late Shift and The War for Late Night, joins the show to talk about the evolution (and de-evolution) of late night.See omnystudio.com/listener for privacy information.

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Battle of the Generations with Versha Sharma Tuesday, March 10, 2026

Baby boomers, millennials, now Gen Z -- they all have their haters. Whichever generation is in their twenties is always walking around with older people rolling their eyes at them. As the former Editor in Chief of Teen Vogue, journalist and millennial Versha Sharma is here to help us understand the seemingly cyclical generational pecking order.See omnystudio.com/listener for privacy information.

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The State of Stand-up with Patton Oswalt Tuesday, March 3, 2026

Though he's a comedic actor, Kal has always felt like the label "comedian" was a sort of stolen valor. That is, until this past year, when he started opening for some of his stand-up friends. This week, Kal calls up Patton Oswalt, a legend in stand-up comedy, to get some advice about getting on stage, what's changed in the comedy world, what hasn't, and what's next.See omnystudio.com/listener for privacy information.

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Sports Betting with Albert Chen Tuesday, February 24, 2026

Since 2018, sports betting has been legalized in 38 states. Plus, sports betting apps have brought gambling right to our fingertips. It turns out this country has a pretty long and fraught history with gambling. Albert Chen, journalist and author of the book, Billion Dollar Fantasy, helps us answer: How dangerous is sports gambling? Is it tainting the games we love to watch? And, how is technology changing the landscape?See omnystudio.com/listener for privacy information.

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Being Offline with Ann Friedman Tuesday, February 17, 2026

Ann Friedman was running popular blogs, newsletters and podcasts before media people flocked to those mediums. But now that the industry is trapped in a rinse and repeat cycle of rising and falling and consolidating, she's getting off the social media content creator wagon and asking a much different question: What does the long game look like?See omnystudio.com/listener for privacy information.

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The American Dream with Rafael Agustin Tuesday, February 10, 2026

Some historians trace this idea of the American dream back to the first European settlers and colonizers. American businessman, James Truslow Adams, popularized the phrase in his book: The Epic of America. But this notion of a single Americcan dream isn't so cut and dry. This week, Kal talks to Rafael Agustin, TV writer, film producer, and author of the memoir, Illegally Yours, about the weight of inheriting someone else's American dream.See omnystudio.com/listener for privacy information.

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The Caitlin Clark Effect with Sarah Spain Tuesday, February 3, 2026

It's been coined, "The Caitlin Clark Effect." For the WNBA's last few seasons, it's translated to a surge in popularity, viewership, and revenue, sparked by one extremely talented, ever-watchabale player. But are women's sports at large suddenly having a moment? Where was that attention two or three decades ago? And what does the future look like for female athletes? Sports journalist, former college athlete, and Good Game podcast host Sarah Spain chats with Kal about the Caitlin Clark Effect amidst all things women's sports.See omnystudio.com/listener for privacy information.

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The Future Is Bilingual with Patty Rodriguez Tuesday, January 27, 2026

Americans weren't always accepting of languages other than English. But nowadays, being bilingual is a huge asset. Kal talks to Patty Rodriguez, the founder of bilingual children's publishing company Lil' Libros, about transforming the narrative of multilingualism in the United States.See omnystudio.com/listener for privacy information.

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Will Technology Replace Us? with Jacob Goldstein Tuesday, January 20, 2026

AI is automating thousands of jobs. But humanity's fear of technology replacing us is nothing new. Journalist and podcaster Jacob Goldstein tells Kal the story of the original Luddites during the early 1800s Industrial Revolution. They talk about how technology changes, how those changes reshape our work, and who historically gets protected and who gets left behind.See omnystudio.com/listener for privacy information.

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Non-Monogamy with Ruby Rare Tuesday, January 13, 2026

Lately, it seems like throuples and open relationships are all the rage. But for many individuals, this way of life is more than a trend. Is non-monogamy suddenly back in style? Or is it something biological? Something that never really went away? Sex educator and author Ruby Rare has a lot to say about it all.See omnystudio.com/listener for privacy information.

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Is the Dynasty Dead? with Alexis Coe Tuesday, January 6, 2026

Kennedys, Clintons, Bushes, Trumps. For better of worse, their names are synonmous with American politics. We're rapidly approaching the 250th anniversary of the American Revolution. But if we openly revolted against the monarchy that long ago, then why does America continue to prop up dynasty families? Or are there signs the dynasty is finally on its way out? Presidential historian Alexis Coe guides us through America's history of powerful political families and what it all means.See omnystudio.com/listener for privacy information.

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Union Busting with Sara Nelson Tuesday, December 30, 2025

As long as unions have existed, so has the effort to undermine them. But why does union busting keep making headlines? And how can workers, even if they're not in a union, use that power to fight back and remake the system? Sara Nelson, President of the Association of Flight Attendants, talks past, present, and future of union busting in America.See omnystudio.com/listener for privacy information.

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A Star is Born... Again with Karina Longworth Tuesday, December 23, 2025

Hollywood is all about remakes. So, it probably doesn't surprise you to hear that the 2018 film, "A Star Is Born," starring Lady Gaga and Bradley Cooper, was its fourth -- yes, fourth! -- iteration. Why do we stick to stories that work? And what is it about this particular story that makes it so quintessential? Kal sits down with film critic, author, and You Must Remember This podcast host, Karina Longworth, to talk about why A Star Is Born... again and again and again.See omnystudio.com/listener for privacy information.

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The Fashion Police with Alok Menon Tuesday, December 16, 2025

Throughout history, certain moments have brought the fashion police and -- not to mention the acutal police -- around in full force. Why should schools, the government, our job, or anyone for that matter stay out of our closets? Kal talks to the poet, comedian, public speaker, and actor Alok Menon about the history of policing clothing as a way to control people's identity.See omnystudio.com/listener for privacy information.