5 Questions with Dave Barry

5 Questions with Dave Barry

From Reasonably Happy with Paul Ollinger by Paul Ollinger

May 28, 2026 · 31 min

About this episode

Paul Ollinger interviews humorist Dave Barry about his career and insights on various topics.

✍️ Follow Paul Ollinger on Substack by clicking here ✍️ Oh my goodness what a fun time I had chatting with Dave Barry on the first episode of 5 Questions , my bite-sized, live-streamed Substack interview show that I’ll be producing in addition to longer-form episodes of Reasonably Happy . Dave’s column was syndicated to hundreds of newspapers around the globe for several decades. He has published dozens of books on myriad topics that sold millions of copies—of books, not topics—in 22 languages. The New York Times called him “the funniest man in America.” (And when has the NYT ever been wrong?) In other words, he’s accomplished an incredible amount in the funny game, and I'm thrilled I got to talk to him. In this fast-moving 30 minute conversation, we talk about: • What he’s looking for in a nursing home. • Advice for me on shepherding my kids through the college search process (even though it doesn’t matter where they end up) • The rock band he plays in with Stephen King, Amy Tan, Roy Blount, Jr., Scott Turow, and many other • Which other authors make him laugh • What Baby Boomers could learn from Gen Z (and vice versa) Listen now and share with all your friends! Also, come see…

People in this episode

Host: Paul Ollinger

Guest: Dave Barry

Topics covered

  • interview
  • humor
  • parenting
  • literature
  • generational differences

Keywords

  • Dave Barry
  • humor
  • parenting advice
  • literature
  • generational differences

Mentioned in this episode

Organizations: The New York Times

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