A Note from James:

One of the funniest guys I’ve ever spoken to—Dave Barry. I always love talking to him. He’s been America’s top humorist since the early ’80s with a syndicated column in 500 newspapers and a long list of bestselling books. This is his third time on the podcast, and his latest book, Class Clown: Memoirs of a Professional Wiseass, is out now.

We get into everything—his process, his adventures, and his signature style of humor that’s made him a legend. It’s always fun with Dave.

Episode Description:

James sits down with Dave Barry to explore the surprising journey behind his new memoir, Class Clown. Dave shares how his humor evolved from playful everyman columns to a more personal, story-driven style. They talk about his outrageous adventures, from picking up his son in the Oscar Mayer Wienermobile to getting booed by telemarketers and dedicating a sewage station in his honor. They also break down the shifting landscape of writing, how syndication shaped Dave’s career, and why modern humor feels trapped in political silos.

This is a rare chance to hear how one of America’s greatest humorists built a career by doing things to write about them—and why his readers became his closest allies.

What You’ll Learn:

• Why Dave Barry was initially reluctant to write a memoir.
• How performing outrageous stunts became central to his writing.
• The critical role of reader engagement in building the success of his humor column.
• How the writing industry—and the path to building an audience—has radically changed.
• Dave’s candid perspective on modern political humor and why neutrality feels impossible today.

Timestamped Chapters:

• [00:00] Introduction to Dave Barry
• [01:00] Writing a Memoir: The Journey Begins
• [02:00] The Humorist’s Approach: Balancing Persona and Reality
• [03:00] Adventures in Journalism: Creating Stories by Living Them
• [05:00] Tactical Humor: Rivalries, Stunts, and Getting Involved
• [08:00] When Humor Becomes the Story: Telemarketers and Public Reaction
• [12:00] Building a Community: How Dave Engaged His Readers
• [17:00] The Syndication Era: How Writing Used to Pay
• [23:00] The New Writing Economy: Substack and the Digital Shift
• [28:00] Assault Humor and the Loss of Neutral Comedy
• [31:00] What’s Next: Substack, Slowing Down, and Florida’s Wild Identity
• [35:00] Writing Novels vs. Columns: Dave’s Fast-Paced Storytelling Style
• [41:00] Stand-Up Comedy and the Influence of Nate Bargatze
• [44:00] Comedy Club Lessons: James on Bombing and Recovery
• [46:00] Criticism: Dave’s Approach to Bad Reviews
• [47:00] Farewell: Dave’s Thoughts on Humor, Writing, and Legacy

Additional Resources:

• 📖 Class Clown: Memoirs of a Professional Wiseass by Dave Barry
• 📖 The Kite Runner by Khaled Hosseini
• 🎤 Nate Bargatze Official Website
• 🎤 Jim Gaffigan Official Website
• 🎤 Hunter S. Thompson’s Fear and Loathing on the Campaign Trail ’72
• 🎤 P.J. O'Rourke’s Official Website (archived)

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