Hanselminutes with Scott Hanselman

Dave Barry is the Class Clown: The Memoirs of a Professional Wiseass

Jun 19, 2025
Dave Barry, a Pulitzer Prize-winning humorist and author known for his witty columns, shares his journey through the ups and downs of writing and promotional tours. He humorously discusses the quirks of technology in relationships and age, the chaos of newspaper syndication, and an amusing encounter on The Tonight Show. Barry also reflects on writing for the Oscars, revealing the burdens of comedic expectations, and indulges in light-hearted tales from his nightlife, emphasizing how humor remains a vital part of life.
Ask episode
AI Snips
Chapters
Books
Transcript
Episode notes
ANECDOTE

Pulitzer Prize Surprise Story

  • Dave Barry missed a trip to Key West because he was called in to the Miami Herald to learn he'd won a Pulitzer Prize.
  • He comforted his son by promising a Nintendo, making his son's happiness the highlight during the award announcement.
ANECDOTE

Hotel Sign Theft for Oprah

  • Dave Barry stole a hotel towel sign for a guest bathroom prank and planned to return it on Oprah.
  • When the original sign was delayed, he stole a replacement sign to keep his promise to appear on the show.
INSIGHT

AI Can't Do Humor Yet

  • Dave Barry observes AI cannot yet capture humor well, despite many attempts.
  • He finds comfort in AI failing to write good humor even as it encroaches on other writing.
Get the Snipd Podcast app to discover more snips from this episode
Get the app