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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Reinventing the Political Parties with Jon Favreau Tuesday, December 2, 2025

These days, it can sometimes feel like the terms Democrat and Republican are confusing -- that they've lost meaning over time. Former Speechwriter and Pod Save America host, Jon Favreau, actually wrote his college thesis about a concept called "realignment." Or, the idea that political parties frequently reinvent themselves and their values. But why do the parties keep changing their identities? Is it as alarming as it sometimes feels to us as voters? And what does that mean for the future of our country?See omnystudio.com/listener for privacy information.

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Another Economic Crash with Michael Lewis Tuesday, November 25, 2025

Back in 2008, it seemed like everyone was talking about the financial crisis. And then came The Big Short, Michael Lewis' book-to-screen story that exposed the corrupt subprime mortgage industry and its impact on the 08 crash. Now, it seems like everyone's wondering: Are we heading towards another big recession? Who would you trust if you were that very man who exposed that broken system in the first place? Kal gets candid with journalist and author Michael Lewis about our financial future, who he trusts with his money, and why.See omnystudio.com/listener for privacy information.

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The Need to Secede with Ed Helms (SNAFU Crossover) Tuesday, November 18, 2025

In this joint episode of HERE WE GO AGAIN and SNAFU, Ed Helms tells Kal the story of a small town that decided to secede from America, only to realize a strong desire to buy beer and party would win out in the end. Then, Ed and Kal call up U.S. historian Richard Kreitner to learn about secession movements in America today, such as Calexit, Texit, and the Greater Idaho Movement.See omnystudio.com/listener for privacy information.

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The Creator Hustle with Lilly Singh Tuesday, November 11, 2025

“Content creator” is not a term they taught me in acting school, yet, the creator economy is turning Hollywood on its head. Internet content was once a springboard to the world of entertainment. It’s now its own billion-dollar industry. Is this just a phase, or are we headed for a future where Clooneys and Pitts are permanently replaced by Rizzlers and Beasts? To find out, we’re talking to the legendary entertainer, actress, writer, producer, and gender equality advocate, Lilly Singh.See omnystudio.com/listener for privacy information.

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Indigenous Theft with Jana Schmieding Tuesday, November 4, 2025

As any indigenous community might tell you, many of this country’s newest trends — from Ayahuasca to hot yoga — are not so new after all. Taking other cultures’ traditions may be as American as baseball, apple pie, and light tax evasion, but where’s the line between borrowing, reinvention, and outright theft? Lakota writer, actress, and comedian Jana Schmieding has some thoughts.See omnystudio.com/listener for privacy information.

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Building the Future with Pete Buttigieg Tuesday, October 28, 2025

The American Society for Civil Engineers gave the U.S. a C on its 2025 Infrastructure Report Card. From public transportation woes to bridge collapses and that pesky plane delays, why can't this country make the jump to straight-A infrastructure land? And will we ever be able to rely on the subway to not get stuck when we have to pee really bad?? Former Secretary of Transportation Pete Buttigieg has some thoughts about how to break the cycle.See omnystudio.com/listener for privacy information.

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Racing to Space with Bill Nye Tuesday, October 21, 2025

From the Cold War to today, space has always been about flexing power. So, why do we keep turning space into a race? What does that say about the future of space exploration -- and about humanity? To answer, only one guy would do: Bill Nye the Science Guy.See omnystudio.com/listener for privacy information.

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Introducing: Here We Go Again With Kal Penn Monday, October 13, 2025

Ever feel like Bill Murray in Groundhog Day, watching the same things happen over and over again? Join Kal Penn on a quest to answer his burning questions about the patterns of the world: Why are we racing to space again? Are we heading towards another financial crash like in '08? And, is non-monogamy back in style?See omnystudio.com/listener for privacy information.