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Here We Go Again With Kal Penn

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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Episodes

Will Technology Replace Us? with Jacob Goldstein

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.

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2026-01-20
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Non-Monogamy with Ruby Rare

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.

2026-01-13
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Is the Dynasty Dead? with Alexis Coe

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.

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2026-01-06
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Union Busting with Sara Nelson

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.

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2025-12-30
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A Star is Born... Again with Karina Longworth

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.

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2025-12-23
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The Fashion Police with Alok Menon

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.

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2025-12-16
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The Youth Vote with Stacey Abrams

Voter turnout among young people is climbing, political affiliations are shifting, and the generation that grew up with social media is flexing their electoral muscle. Stacey Abrams is renowned for getting 800,000 people registered to vote in 2020. So, why is the youth vote so important? What's changed since 18 year olds gained the right to vote in 1971? And how have forces like Rock the Vote or TikTok shaped young people's POV on politics?

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2025-12-09
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Reinventing the Political Parties with Jon Favreau

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?

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2025-12-02
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Another Economic Crash with Michael Lewis

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.

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2025-11-25
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The Need to Secede with Ed Helms (SNAFU Crossover)

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.

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2025-11-18
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The Creator Hustle with Lilly Singh

“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.

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2025-11-11
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Indigenous Theft with Jana Schmieding

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.

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2025-11-04
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Building the Future with Pete Buttigieg

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.

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2025-10-28
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Racing to Space with Bill Nye

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.

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2025-10-21
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Introducing: Here We Go Again With Kal Penn

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.

2025-10-13
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