The Gray Area with Sean Illing

The Gray Area with Sean Illing

https://feeds.megaphone.fm/theezrakleinshow
7.4K Followers 740 Episodes
The Gray Area with Sean Illing takes a philosophy-minded look at culture, technology, politics, and the world of ideas. Each week, we invite a guest to explore a question or topic that matters. From the the state of democracy, to the struggle with depression and anxiety, to the nature of identity in the digital age, each episode looks for nuance and honesty in the most important conversations of our time. New episodes drop every Monday. From the Vox Media Podcast Network.

Episode List

America is football

Jan 26th, 2026 9:00 AM

Why do we love football so much? Why does this sport dominate American culture in a way nothing else can? Why does it feel essential even to people who barely like sports? And what does it say about us that we keep watching, even as the risks and contradictions become harder to ignore? Today’s guest is Chuck Klosterman, cultural critic and bestselling author, whose new book Football tries to explain the game at the height of its power. Sean and Chuck talk about how football became the defining spectacle of modern America, why it’s easily the best television show we’ve ever seen, and why it presents a ton of moral dilemmas we can’t really solve.  Host: Sean Illing (@SeanIlling) Guest: Chuck Klosterman, author of Football We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.And you can watch new episodes of The Gray Area on YouTube. Learn more about your ad choices. Visit podcastchoices.com/adchoices

How we built a government that can’t build anything

Jan 12th, 2026 9:00 AM

Why is it so hard for America to build things? Bridges take years to construct. Housing costs are soaring. Transit systems are crumbling. And we’re struggling to update our infrastructure to prepare for the climate crisis. Even when there’s broad agreement that something needs to be done, collective action feels impossible. Why is that? Today’s guest is Marc Dunkelman, author of Why Nothing Works, a book about the modern American experience of watching government fail. He argues that by giving too many people the power to say “no,” we’ve stymied our collective progress. Marc and Sean discuss an inherent tension in American politics: the need for effective, centralized power and a deep fear of its abuse. They trace how that tension has played out across American history, from the clashes between Jefferson and Hamilton, through the New Deal’s Tennessee Valley Authority, to the backlash against figures like Robert Moses. Marc argues that our current system — born out of a reaction to too much top-down authority during the late 20th century — has produced paralysis, dysfunction, and a deep distrust of government. Host: Sean Illing (@SeanIlling) Guest: Guest: Marc Dunkelman (@MarcDunkelman), author of Why Nothing Works: Who Killed Progress — and How to Bring It Back. We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members This episode was supported by a grant from Arnold Ventures. Vox had full discretion over the content of this reporting. Learn more about your ad choices. Visit podcastchoices.com/adchoices

It’s okay to not be okay

Dec 22nd, 2025 9:00 AM

It’s not always the most wonderful time of the year. Every December, we’re told to be merry and stay positive. But a lot of us don’t feel that way. And when we don’t, the pressure to be happy makes everything worse. Sadness feels like failure. Grief feels like a personal mistake. Depression becomes something to hide. But what if dark moods aren’t problems to fix? What if they’re part of being human? Today’s guest is philosopher Mariana Alessandri, author of Night Vision, a book about how to honor the emotions we usually try to outrun. It’s not a celebration of sadness, but Alessandri calls bullshit on the culture of toxic positivity and the idea that happiness is something we’re supposed to choose on command. Sean and Mariana talk about why Americans are addicted to the light, why “cheering people up” often backfires, how Stoicism shaped our emotional habits, and what it looks like to sit with grief instead of shaming ourselves for feeling it. Host: Sean Illing (@SeanIlling) Guest: Mariana Alessandri (@mariana.alessandri), associate professor of philosophy at the University of Texas-Rio Grande Valley and author of Night Vision: Seeing Ourselves Through Dark Moods. We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. This holiday season, your membership goes further: when you join Vox as an annual Member, we’ll gift a free membership to a reader who can’t afford it. By joining today, you’ll get 30% off for an annual membership, and we’ll match your membership. And if you can’t afford it, visit that same link to apply for a free membership through our gift program. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Forgiveness is optional

Dec 15th, 2025 9:00 AM

You have to forgive people who wrong you…right? The world is filled with injustice and wrongdoing, and to live in the world — to not be consumed by anger — forgiveness is necessary. At least that’s what we’re told over and over again: By forgiving, we can set ourselves free.But is there a cost to forgiveness? Are we forgiving too quickly and too often? Today’s guest is philosopher Myisha Cherry, whose book Failures of Forgiveness critiques our cultural obsession with forgiving those who have done us wrong. She’s not against forgiveness — that would be weird — but she says we ought to be more intentional about why we do it, more aware that the expectation to practice forgiveness often lands on the most vulnerable people, and more concerned about what gets lost when we treat forgiveness as the only path to healing.  Sean and Myisha discuss the 2015 Charleston church shooting, the legacy of slavery, and the real difference between accountability, reconciliation, and simply moving on. Host: Sean Illing (@SeanIlling) Guest: Myisha Cherry (@myishacherry), associate professor of philosophy at the University of California Riverside, and author of Failures of Forgiveness: What We Get Wrong and How to Do Better. This episode was made in partnership with Vox's Future Perfect team. Vox had full discretion over the content of this reporting. We would love to hear from you. To tell us what you thought of this episode, email us at thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of The Gray Area on YouTube.Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. This holiday season, your membership goes further: when you join Vox as an annual Member, we’ll gift a free membership to a reader who can’t afford it. By joining today, you’ll get 30% off for an annual membership, and we’ll match your membership. And if you can’t afford it, visit that same link to apply for a free membership through our gift program. Learn more about your ad choices. Visit podcastchoices.com/adchoices

The pornification of everything

Dec 8th, 2025 6:00 AM

Sean’s guest today is Daniel Kolitz, author of a remarkable Harper’s story on “gooning.”  They talk about this emerging subculture and how it reflects back on the larger world, from the economics of attention to the rise of short-form everything. Kolitz explains why the Gooniverse isn’t just about porn, how hyperkinetic media rewires our sense of pleasure and patience, and why this is really a story about how society is changing in ways we might not like. Host: Sean Illing (@SeanIlling) Guest: Daniel Kolitz, author of The Goon Squad We would love to hear from you. To tell us what you thought of this episode, email thegrayarea@vox.com or leave us a voicemail at 1-800-214-5749. Your comments and questions help us make a better show. And you can watch new episodes of ⁠⁠The Gray Area on YouTube⁠⁠.. Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members. This holiday season, your membership goes further: when you join Vox as an annual Member, we’ll gift a free membership to a reader who can’t afford it. By joining today, you’ll get 30% off for an annual membership, and we’ll match your membership. And if you can’t afford it, visit that same link to apply for a free membership through our gift program. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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