Bill welcomes back — comedian, Uber driver, and former strip club DJ Doug Phelps — for a hilariously honest and unexpectedly heartfelt episode. It’s been a while since Doug has been in the studio, and Bill can’t help but wonder… did time away leave Doug with a few hurt feelings?

Bill kicks things off by congratulating Doug on the official proclamation he received for 15 years of fundraising for the Breast Cancer Coalition of Rochester. As Bill says, “Doug is the only guy who spent 15 years thinking about boobs and people love him for it. What a hero!” Doug reflects on what the honor meant to him, how the golf and bowling tournaments he created have evolved, and why he may be ready to hand part of the legacy over. The conversation goes deeper than expected — what has 15 years of giving taught him about people, identity, and what lasts after you stop doing “the thing” you’re known for?

Then the guys pivot to baseball and break down the epic 2025 World Series between the Dodgers and the Blue Jays — recorded before Game 7 in Toronto. From one of the longest World Series games in history (wrapping up near 3 AM Eastern!) to the flag-waving field runner in Game 6, Bill and Doug talk about streakers, strategists, and the bizarre psychology of people who jump onto the field knowing they’ll be tackled immediately. Yes, even Morganna the Kissing Bandit makes an appearance in the conversation — as does Brighton’s own Ernie Clement, who’s been crushing it for Toronto.

Doug also tells wild, human, “you can’t make this up” stories from his three very different careers — behind the wheel, behind the mic, and behind the DJ booth. From ridiculous to redeeming, one story even restored his faith in humanity, sending the guys into a thoughtful conversation about drugs, class, and the messy, unexpected ways life humbles everyone.

The episode closes with two men in their 50s reflecting on reinvention — Doug’s nomadic, nontraditional life path and Bill’s shift from radio to podcasting, now pursuing a master’s degree. What would they tell their 25-year-old selves? Warn him… or hype him up?

It’s funny. It’s honest. It’s unexpectedly deep. And it’s “Dougie Fresh” back in the studio, enjoy!


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