This Past Weekend w/ Theo Von

Trevor Wallace, a comedian and viral content creator known for his sketches and the podcast Stiff Socks, joins the conversation with a whirlwind of hilarious anecdotes. He shares funny dating app misadventures and a nostalgic look at growing up in the suburbs. Trevor's take on the TikTok algorithm and tales from crashing a Kyle convention are comedic gold. He reflects on the golden era of internet porn and the absurdity of modern dating life, blending laughter with a candid look at adolescence and self-discovery.

Malcolm Gladwell, a celebrated author and journalist known for his best-selling books and the podcast Revisionist History, shares deep insights in a lively chat. He delves into the surprising complexities of human behavior, discussing everything from the societal implications of hair to the often flawed nature of job interviews. The impact of AI on our lives is also explored, alongside a critical look at policing and the narratives surrounding it. Through humor and reflection, Gladwell navigates the interplay between technology, culture, and personal identity.

Brianna Chickenfry, a dynamic podcaster and content creator from Barstool Sports, shares her vibrant journey from a wild childhood in South Boston to rising fame on TikTok. She and Theo chat about hilarious tales of stealing bras, her decision to quit school for Barstool, and her amusing beef with Frank the Tank. They also explore the quirks of childhood memories, the balancing act of friendship and mental health, and the ups and downs of navigating life in New York City. Expect plenty of laughs and candid reflections!

Will Sasso, a talented actor and comedian known for MadTV and co-host of the AI-driven podcast Dudesy, shares his latest adventures with Theo. They dive into their crazy past, including almost getting sued by Tom Brady and memorable moments from MadTV. Will also discusses the quirks of his AI podcasting experience, societal shifts influenced by tech, and reflections on individuality in both life and baseball. Expect a mix of humor and nostalgia as they explore the impact of AI on creativity and the comedic landscape.

Reflecting on a memorable visit to an Asian church, the host shares humorous insights on motherhood and the unique qualities that make moms special. Nostalgia takes center stage as they recount eccentric childhood tales and explore life's unpredictable journey. Personal anecdotes about therapy, whimsical childhood memories, and even early experiences with door-to-door meat sales keep the conversation lively. With a mix of humor and heartfelt reflections, the host navigates through life's ups and downs while engaging with listeners.

Rainn Wilson, best known for his iconic role as Dwight Schrute on The Office, is an actor, writer, and producer who brings wit and wisdom to the conversation. He shares his journey in Hollywood, discussing the balance between spirituality and showbiz. They tackle the challenges of modern life distractions, nostalgia for childhood creativity, and the pursuit of genuine connections. Rainn also humorously examines societal issues like education reform and the search for joy in a chaotic world, all wrapped in lighthearted banter.

Glenny Balls, an entertainer and podcaster at Barstool Sports, chats with Theo about his Long Island Italian upbringing and the wild story of landing a job at Barstool. They dive into humorous takes on lovemaking to Billy Joel, reminisce about nostalgic prom experiences, and discuss their culinary misadventures with seafood. Glenny also shares insights on interviewing women from OnlyFans, emphasizing empowerment in the adult industry, all sprinkled with personal anecdotes and playful banter.

John Mulaney, an Emmy-winning comedian and writer known for his sharp observational humor, opens up about his tumultuous last few years. He discusses his unconventional path to recovery, including experiences with rehab and the challenges he faced during addiction. The conversation touches on the importance of humor in healing and rewiring oneself for the better. Mulaney also shares insights into balancing personal struggles with the pressures of comedy, offering a candid look at life, laughter, and the quest for authenticity.

Stavros Halkias, a hilarious stand-up comedian and host of Stavvy’s World, dives into a plethora of topics. He shares wild tales from his Greektown upbringing and critiques the absurdity of bad AI comedy. The conversation also drifts to Puerto Rican gym bros and explains the real pain behind the Bud Light controversy. Stavros reflects on his departure from his old podcast, explores the complexities of cultural identity, and even offers a comedic take on the quirks of relationships. It's a light-hearted yet insightful exploration filled with laughter!

Theo shares his adventures from Texas to Louisiana, diving into everything from bald eagle crimes to odd messages on sheets. He reflects on the Nashville shooting and the quest for purpose while tackling modern life's overwhelm. Fun anecdotes about meeting family and humor about a local news story keep it light. Theo also discusses men's health, brand authenticity, and the evolving conversation around identity and consumer behavior, all while encouraging listeners to engage in self-reflection and seek meaningful connections.