Second Thought

The Free Press

Second Thought is a new podcast from The Free Press tackling pop culture with a sharp, open-minded, and funny point of view. Hosted by Free Press co-founder Suzy Weiss and comedian Dan Ahdoot (Cobra Kai, Undercooked), the show cuts through the noise to explain what everyone is watching, talking about, arguing over, and quietly obsessed with—or will be soon. Expect cutting commentary, unexpected guests, and cultural translating for Gen Xers who want to understand their kids, millennials who are starting to feel like boomers, and everyone in between.

Episodes

  1. 1 DAY AGO

    Legendary Screenwriter on Hollywood, the Future of Entertainment—and Compulsive Gambling

    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 strange psychology of risk. Loeb opens up about creating imaginary friends whose net worths he obsessively tracked as a child, which developed into a gambling addiction that has checkered his adult life. He recounts losing fortunes shorting Tesla and spiraling through blackjack systems in Bahamian casinos—all while becoming a renowned Hollywood writer. Suzy and Allan unpack the future of storytelling in the age of AI, why Hollywood may not be dying nearly as fast as everyone claims, Tom Holland’s attachment style, and why baseball is “the crystal meth of gambling.” Then, comedian Dan Ahdoot joins the panel for a rundown of the week’s biggest culture stories—from the hantavirus panic to Billie Eilish’s new James Cameron-directed documentary, to the roast of Kevin Hart (the women took the night!). It’s a funny and moving episode that you won’t want to miss. Want more Suzy? Subscribe to “The Free Press” today to get her weekly culture column—fresh in your inbox every Friday afternoon: https://www.thefp.com/s/second-thought?sort=new Follow Suzy Weiss: Twitter: https://x.com/SnoozyWeiss Instagram: https://www.instagram.com/suzyisonline/ Follow Dan: Twitter https://x.com/standupdan Instagram: https://www.instagram.com/standupdan/ Subscribe to The Free Press: https://www.thefp.com/subscribe

    59 min

  2. 8 MAY

    Would You Travel to Korea for a New Face? Ben Kawaller Did.

    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.  They also discuss Ben’s new podcast series, “Strange Bedfellows,” which explores the complicated political and cultural history of the LGBTQ coalition. From the shift from “gay” to “queer,” to the tensions within the movement itself, the discussion digs into how identity politics, gender ideology, and coalition-building reshaped American culture over the last several decades. Plus: theater etiquette collapse, the Met Gala, Jeff Bezos funding the arts, Spirit Airlines shutting down, why nobody knows how to behave in public anymore—and whether fashion is actually art. Smart, funny, provocative, and completely unhinged. You don’t want to miss it. Want more Suzy? Subscribe to “The Free Press” today to get her weekly culture column—fresh in your inbox every Friday afternoon: https://www.thefp.com/s/second-thought?sort=new Follow Suzy: Twitter: https://x.com/SnoozyWeiss Instagram: https://www.instagram.com/suzyisonline/ Follow Dan: Twitter https://x.com/standupdan Instagram: https://www.instagram.com/standupdan/ Follow Ben: Twitter: https://x.com/benkawaller Instagram: https://www.instagram.com/benkawaller/ Subscribe to “The Free Press”: https://www.thefp.com/subscribe

    38 min

  3. 1 MAY

    Inside the Reality TV Machine with Sophia Rivka Rossi

    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 psychics, holistic healers, and empaths who insist they can clear your energy over WhatsApp. Then, joined by co-host Dan Ahdoot, the trio dives into the buzziest stories of the week: the shooting at the White House Correspondents’ Dinner (Suzy was in the room), the controversial new Michael Jackson biopic, Megan Thee Stallion’s very public breakup—and more. It’s mandatory listening. Follow Suzy Weiss: Twitter: https://x.com/SnoozyWeissInstagram: https://www.instagram.com/suzyisonline/ Follow Dan: Twitter https://x.com/standupdan Instagram: https://www.instagram.com/standupdan/ Follow Sophia: Instagram: https://www.instagram.com/rivfifi/ Substack: https://www.betweenfriendsmedia.com/p/between-friends Subscribe to The Free Press: https://www.thefp.com/subscribe

    45 min

  4. 24 APR

    Claudia Oshry Gets Real: Internet Fame, Blake Lively, GLP-1s & More

    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 famous,” getting canceled early in her career, and her relationship to fame, confidence, and public opinion. Then, Dan Ahdoot joins the conversation to dive into the pop culture stories of the week: why Blake Lively might be misunderstood, the too-online intensity of Olivia Rodrigo fans, Demi Lovato’s redemption arcs, the fraught personal dynamics of GLP-1s—and more. Follow Suzy: Twitter: https://x.com/SnoozyWeiss Instagram: https://www.instagram.com/suzyisonline/ Follow Dan: Twitter https://x.com/standupdan Instagram: https://www.instagram.com/standupdan/?hl=en Follow Claudia: Instagram: https://www.instagram.com/girlwithnojob/ Subscribe to The Free Press: https://www.thefp.com/subscribe

    56 min

  5. 20 APR

    Recession Indicators with Suzy and Dan

    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/standupdan/with_replies Instagram: https://www.instagram.com/standupdan/?hl=en Subscribe to The Free Press: https://www.thefp.com/subscribe

    25 min

  6. 17 APR

    We’re All Living in Casey Neistat’s World

    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 old technology, and how his career illustrates Andy Warhol’s infamous prediction that “In the future, everyone will be world-famous for 15 minutes.” Plus: the creative power of brothers, Lena Dunham, and who inherited the mantle of Jackass. He also answers some harder questions: Has the rise of the creator economy and the parasocial relationships that came with it been a net positive? Is it possible to win the algorithm without exploiting your audience? Can artistic expression survive the onslaught of artificial intelligence? On all fronts, the man who saw around the corner of our last media revolution isn’t so sure. Subscribe to Second Thought for new episodes every week. Follow Suzy Weiss: Twitter: https://x.com/SnoozyWeiss Instagram: https://www.instagram.com/suzyisonline/ Subscribe to The Free Press: https://www.thefp.com/subscribe

    1hr 21min

  7. 3 APR

    Introducing: Second Thought with Suzy Weiss

    Pop culture is fun—but we take it very seriously. And so should you. Catch Second Thought every Friday wherever you get your podcasts.

    29 sec

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About

Second Thought is a new podcast from The Free Press tackling pop culture with a sharp, open-minded, and funny point of view. Hosted by Free Press co-founder Suzy Weiss and comedian Dan Ahdoot (Cobra Kai, Undercooked), the show cuts through the noise to explain what everyone is watching, talking about, arguing over, and quietly obsessed with—or will be soon. Expect cutting commentary, unexpected guests, and cultural translating for Gen Xers who want to understand their kids, millennials who are starting to feel like boomers, and everyone in between.

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