From an early age, writer, director, and producer Judd Apatow has been obsessed with comedy. What started as a quest to interview comedians for his high school radio station ultimately evolved into one of the most prolific careers in Hollywood today, with hits like “The 40 Year Old Virgin,” “Knocked Up,” and “Anchorman.” Now, Apatow is looking backwards. His new book, “Comedy Nerd,” is a visual memoir of his decades in the business, working with a who's who of the biggest names in comedy.

Kara and Judd talk about how he reimagined the genre of raunchy, R-rated comedies about stunted adolescence; what he got right about American masculinity in the mid-and-late 2000s; and his recent pivot to making documentaries about some of the greatest comedians of the modern era. They also discuss whether AI can be funny and the ways politics is shaping comedy right now.

Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.

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EST078 - The Pur is Cast