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Second Thought

Second Thought

The Free Press 9 episodes Latest May 28, 2026

Second Thought is a new podcast from The Free Press that offers a sharp, open-minded, and funny take on pop culture. Hosted by Free Press co-founder Suzy Weiss and comedian Dan Ahdoot, the show cuts through the noise to explain what everyone is watching, talking about, arguing over, and quietly obsessed with. Expect cutting commentary, unexpected guests, and cultural translating for Gen Xers, millennials, and everyone in between.

Episodes

Jeff Ross on Tom Brady, Trump, and the Roast of Kevin Hart Jun 12, 2026 4403 Roast comedy is one of the last places where truly unfiltered commentary still lands in public, says “Roastmaster General” Jeff Ross. Few people understand the art of the insult better than Ross, who has presided over the brutal, hilarious takedowns of everyone from Joan Rivers and Justin Bieber to Charlie Sheen. Today, he joins Suzy Weiss to break down his new Netflix special, Take a Banana for
I Am Not a Robot (but My Boyfriend Was) Jun 5, 2026 4413 For a year, tech writer Joanna Stern turned herself into an AI guinea pig. She let artificial intelligence into every corner of her life: testing robot assistants, commuting in autonomous vehicles, reading AI bedtime stories to her children, and even going on a road trip with her AI boyfriend, Evan.  That experiment became her new book, I Am Not a Robot. In this episode, Joanna breaks down what w
Scooter Braun on Taylor Swift, Kanye West, and Becoming the Internet’s Villain May 28, 2026 5147 Scooter Braun reflects on how he became one of pop music’s most powerful kingmakers, helping to engineer the careers of Justin Bieber and Ariana Grande—and the controversies that reshaped his public image, from Kanye West’s antisemitic spiral, which ended their relationship, to the Taylor Swift masters dispute that turned Braun into one of the internet’s biggest villains. Braun says he barely kne
‘Call Her Daddy,’ ‘Euphoria,’ and the New Template for Girlhood May 22, 2026 3982 In this episode, Suzy Weiss sits down with writer Freya India to discuss how the internet, influencer culture, and therapy-speak have made adolescence more miserable than ever for girls. India’s new book, Girls®: Generation Z and the Commodification of Everything, examines how algorithm-driven platforms push young users toward extremes in beauty, body image, mental health, and relationships. It’s
Legendary Screenwriter on Hollywood, the Future of Entertainment—and Compulsive Gambling May 15, 2026 3512 Read Allan Loeb in The Free Press: https://www.thefp.com/p/hi-my-name-is-allan-and-im-a-compulsive On this week’s episode of Second Thought, Suzy Weiss sits down with screenwriter Allan Loeb—he wrote, among other films, 21, Wall Street: Money Never Sleeps, The Dilemma, and Just Go with It—for a wide-ranging, entertaining conversation about Hollywood, AI anxiety, compulsive gambling, and the stran
Would You Travel to Korea for a New Face? Ben Kawaller Did. May 8, 2026 2307 Ben Kawaller just flew to South Korea to inject salmon sperm into his face. On this week’s episode of “Second Thought,” Suzy Weiss, Dan Ahdoot, and Ben unpack the bizarre rise of the male beauty economy. Ben recounts his surreal trip to Seoul, where he underwent a series of cutting-edge cosmetic procedures—including “Crowtox,” laser treatments, and the infamous Rejuran salmon DNA injections. 
Inside the Reality TV Machine with Sophia Rivka Rossi May 1, 2026 2689 From The Hills to Glee to the rise of girlboss media—Sophia Rivka Rossi has seen and shaped our culture from the inside out. Today, she pulls back the curtain. On this week’s episode of Second Thought, Sophia joins Suzy Weiss to unpack the machine behind reality TV, the secret sauce behind Ryan Murphy’s dominance, and what happens when you finally stop outsourcing your inner life to online p
Claudia Oshry Gets Real: Internet Fame, Blake Lively, GLP-1s & More Apr 24, 2026 3336 On this week’s episode of Second Thought, Suzy Weiss sits down with comedian, media mogul, and professional pop culture savant, Claudia Oshry, for a conversation about what it actually takes to survive, and even thrive, online. As host of one of the internet’s most popular pop culture podcasts—The Toast, which she hosts with her sister Jackie—Claudia talks about the reality of being “internet f
Recession Indicators with Suzy and Dan Apr 20, 2026 1513 Today, Suzy Weiss sits down with Dan Ahdoot to talk about the big stories of the week, including Justin Bieber’s Coachella performance, the supposed unmasking of Satoshi Nakamoto, and whether $40 is too much to pay for half a rotisserie chicken. Follow Suzy Weiss: Twitter: https://x.com/SnoozyWeiss Instagram: https://www.instagram.com/suzyisonline/ Follow Dan Ahdoot: Twitter: https://x.com/stan
We’re All Living in Casey Neistat’s World Apr 17, 2026 4878 Today, on our inaugural episode of Second Thought, Suzy Weiss sits down with one of the most influential people in YouTube’s history: Casey Neistat. Casey has millions of followers and billions of views to his name—and he saw early on that YouTube would change everything. It certainly changed his own life. In this conversation, Casey talks about riding the wave of the YouTube tsunami, his love of
Introducing: Second Thought with Suzy Weiss Apr 3, 2026 29 Pop culture is fun—but we take it very seriously. And so should you. Catch Second Thought every Friday wherever you get your podcasts.

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