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
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