Episode 042 | August 15, 2026 – I Thought Rihanna Was a One-Hit Wonder

Before D.B. closes the book on Biloxi, Mississippi, there are a few people—and one spectacularly bad prediction—he needs to tell you about. After the devastation and heavier memories of Hurricane Katrina, this chapter goes back to the people who made D.B.'s time on the Gulf Coast unforgettable. There's Fat Guy, the intimidating punk-rock-looking radio guy who taught D.B. something unexpected about pedicures. There's Grady, the ball of energy who helped the new guy from New Jersey discover Biloxi. And then there's Caroline—a regular caller who became an unofficial character on D.B.'s radio show and knew exactly how to get the phones ringing. Twenty years later, she's built an online following of her own as Mississippi Kween. But D.B. saved his worst prediction for last. Back in 2005, an up-and-coming artist recorded a custom liner saying D.B.'s name and promoting his radio show. After Katrina, while cleaning out his desk, D.B. found the CD and threw it away. Why? Because he figured she'd probably be a one-hit wonder. Her name was Rihanna. Whoops. On this episode: Meet one of D.B.'s favorite characters from his radio career: Fat Guy. How a punk-rock-looking dude convinced D.B. to get his first pedicure. Remembering Grady and D.B.'s introduction to life on the Gulf Coast. How regular callers became unofficial characters on D.B.'s nightly radio show. The incredible New Jersey connection D.B. discovered with Caroline. How Caroline went from radio-show troublemaker to Mississippi Kween. Why radio has always been "theater of the mind." And the story of the Rihanna recording D.B. wishes he had kept forever. Sometimes the things you throw away become a lot more valuable twenty years later. Next episode: D.B. finally leaves Biloxi—and the Radio Journey heads somewhere completely different. Follow D.B.'s Radio Journey from the beginning starting with Episode 030. Listen to every episode at www.dbnycepodcast.com