Here We Go Again With Kal Penn

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.

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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.

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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.

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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?

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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?

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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.

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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.

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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.

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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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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.

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