reSee.it Podcast Summary
Today's episode features Theo Von hosting with Will Sasso. The show opens with plugs for Grey Block Pizza at 1811 Pico Boulevard in Los Angeles and Skillshare, an online learning platform with over 20,000 classes in business, design, technology and more. Skillshare promotes classes like presentation essentials, how to share ideas that inspire action, sketch for beginners, designing your own app, how to make Android apps, and trap music production, offering This Past Weekend listeners two months of unlimited access for 99 cents at Skillshare.com/Theo.
Theo introduces Will Sasso, describing him as a hugely joyful presence and one of the top men alive, with playful humor about the hallway they share. The two exchange Christmas greetings and debate about Merry Christmas vs Happy Holidays, reflecting their easy banter and affection for in-person warmth.
The conversation veers from holiday language to childhood and career. Will jokes about his stature and being in the top tier of Men’s Magazine’s “top 200” list, and they trade stories about weight, food, and pizza decisions, including the pizza box dilemma and a nod to era-typical indulgences. They discuss Will’s career as a MADtv and improv performer, his weight, and how he got into acting and stand-up. He recalls meeting greats like Dick Van Dyke, and notes he’s never met Craig T. Nelson, while recounting other Hollywood legends with humor and humility. Theo and Will reflect on how comedy has evolved in the era of political correctness and white guilt, with Will noting that podcasts still allow freer language, while acknowledging the push to be mindful of others’ feelings.
The talk moves to Canada and small-town life. Will, who’s Canadian, describes Ladner outside Vancouver, describing memories of a private investigator pedophile era and childhood anecdotes, then pivots to his Arctic shoot, the Nunavut capital, and a fascinating encounter with a barbecue entrepreneur from Quebec who fueled his respect for northern resilience. They recall the Arctic environment, dog sledding, and the contrast with American life, including differences in social norms and humor.
They discuss the “cult” idea around Chris D’Elia, the possibility of a real-world following, and brainstorm a satirical Santa character Will might perform as on stage. They also consider whether Will should pursue live road work, or a stand-up persona, and contemplate how comedy exists as an art form under siege, balancing risk, accountability, and freedom of expression. They touch on the aging of show business, the dynamic of the This Past Weekend crew, and the possibility of future collaborations, while keeping the conversation light, profane, affectionate, and Christmas-season specific. They close with a festive, chaotic energy, wishing listeners a Merry Christmas from Will Sasso and Theo Von, and teasing more holiday content to come.