Best of 2025: The Second Annual 'Tennies'

Live from the glamorous crossroads of America (a Best Western in Sheboygan, Michigan), Dave and Milt roll out the red carpet—or at least a slightly wrinkled hallway runner—for the Second Annual Tennies, our totally prestigious, minimally regulated awards honoring the very best moments of the podcast year that was. This is the episode where we look back, point, laugh, occasionally wince, and then laugh harder. We hand out trophies (imaginary, but emotionally heavy) for categories like Best Guest, Worst Tale of Woe, Best Use of Creepy AI, and—because we are who we are—the highly competitive Best Penis Joke. It’s a night filled with surprise guest appearances, unnecessary musical detours, tech hiccups that absolutely should not have happened, and stories that somehow got more awkward with time. Between heartfelt moments, holiday chatter, listener emails, and Milt doing things that can only be described as “very Milt,” the Tennies once again prove that when you give two guys microphones and zero adult supervision, magic—questionable, chaotic magic—can still happen. Topics 01:29 – Opening Monologue: Big Energy, Questionable Confidence 04:30 – Best Use of Creepy AI (We’re Sorry, Humanity) 12:22 – Best Guest (Actual Talent Appears) 17:39 – Worst Tale of Woe (Pain + Time = Comedy) 20:38 – Best Invention (Patent Pending, Probably Not) 23:43 – Best Time Machiner Email 34:10 – Parenting Jokes We Immediately Regretted 34:29 – The Susanna Hoffs Concert That Broke Our Brains 35:44 – Best Machiner Email: Champion Emerges 37:21 – Dreams, Delusions, and Podcast Therapy 39:47 – Classic Milt Moments (A Deep Bench) 43:18 – Things We Definitely Didn’t See Coming 53:53 – Rapid-Fire Chaos 56:48 – (We don’t mean to be dicks, but …) Best Penis Jokes