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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.

The Gray Area with Sean Illing

Open a browser and you can feel it instantly: everything online just feels… worse. Search results that look like ads. Social feeds that you don’t control. Streaming platforms that are packed with ads. Services that used to be free, but are now behind paywalls. It’s not your imagination — it’s enshittification, the process by which good platforms turn bad… and it’s starting to happen outside the internet as well.

Sean’s guest today is Cory Doctorow, author of Enshittification: Why Everything Suddenly Got Worse and What to Do About It. They discuss how the web became enshittified, why monopolies are the true engine behind our digital decay, and what it would mean to build a freer, fairer, and more human internet.

Host: Sean Illing (@seanilling)

Guest: Cory Doctorow (https://x.com/doctorow), author of Enshittification: Why Everything Suddenly Got Worse and What to Do About It.

We’d love to hear from you. Tell us what you thought of this episode at tga@voxmail.com or leave 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
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The Great Enshittening

Is America at a tipping point?

Sean Illing talks with Barbara Walter, one of the world’s leading experts on violent extremism and domestic terror. She’s the author of How Civil Wars Start, about how democracies unravel from within, and a professor at UC San Diego’s School of Global Policy and Strategy.

Walter talks to Sean about the warning signs she’s seeing in the US, why polarization and party identity become combustible, and what lessons we can draw from other countries. They also discuss what an American civil war might look like in the 21st century, the social and informational dynamics that accelerate breakdown, and whether America still has a path away from the brink.

Host: Sean Illing (@SeanIlling)

Guest: Barbara Walter, professor at UC San Diego and author of How Civil Wars Start

We would love to hear from you. To tell us what you thought of this episode, email us at tga@voxmail.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
Learn more about your ad choices. Visit podcastchoices.com/adchoices

America chose violence. Now what?

We like to think of memory as a record of the past. But that’s not really what it is. Memory doesn’t keep the past — it can also remake it. It stitches fragments into stories, and those stories — true or not — are what we end up calling our life, and sometimes, our collective history.

Sean’s guest today is Charan Ranganath, a neuroscientist and author of a book called Why We Remember. The two discuss the strange alchemy of remembering and how the stories our minds create end up creating us.

Host: Sean Illing (@SeanIlling)

Guest: Charan Ranganath, neuroscientist and author of Why We Remember

We would love to hear from you. To tell us what we thought of this episode, email us at tga@voxmail.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
Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's worth remembering?

This week, Sean talks with Emily Baker-White, author of Every Screen on the Planet, about why TikTok feels uniquely addictive, how it turned social media into a push-not-pull entertainment feed, and what happens when human editors inside the company can override the algorithm.

A few days after they spoke, TikTok was in the headlines again. So they jumped on a follow-up call to unpack the latest twists in the saga of who will ultimately control the app's US-operations.

Host: Sean Illing (@SeanIlling)

Guest: Emily Baker-White, reporter and author of Every Screen on the Planet: The War Over TikTok

The Gray Area has been nominated for a Signal Listener’s Choice Award. Vote for The Gray Area here: https://vote.signalaward.com/PublicVoting#/2025/shows/genre/thought-leadership

We’d love to hear from you. Email us at tga@voxmail.com or leave a voicemail at 1-800-214-5749. Your questions and feedback help us make a better show.

Watch full episodes of The Gray Area on YouTube.

Listen ad-free by becoming a Vox Member: vox.com/members
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why TikTok matters

Bill McKibben has spent four decades warning us about climate change. Much of what he predicted has come true. And yet, his new book Here Comes the Sun is more hopeful than you might expect. That’s because, for the first time, we have a genuine alternative: Solar and wind energy are now the cheapest, fastest-growing sources of power on Earth. The revolution has already begun.

This week, Sean is joined by McKibben to talk about the peril and promise of this moment. They explore how close we are to catastrophe, why each fraction of a degree of warming matters, and how the fossil fuel industry is fighting a desperate last stand. They also discuss the politics of energy in the age of Trump, why Texas and Utah may hold surprising lessons, and how cheap, abundant power could transform not just the climate fight but democracy itself.

Host: Sean Illing (@SeanIlling)

Guest: Bill McKibben, climate activist and author of Here Comes the Sun

We’d love to hear from you. Email us at tga@voxmail.com or leave a voicemail at 1-800-214-5749. Your questions and feedback help us make a better show.

⁠⁠This episode was made in partnership with Vox's Future Perfect team.

Watch full episodes of The Gray Area on YouTube.

Listen ad-free by becoming a Vox Member: vox.com/members

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The sun will save us

Free speech is often treated as a timeless and sacred right. But what if it’s more myth than reality?

This week, Sean is joined by historian Fara Dabhoiwala, author of What Is Free Speech? They trace the history of free expression from 18th-century pamphleteers, to John Stuart Mill, to the digital platforms that dominate our lives today.

They explore why speech is never just “speech,” how context and power shape who gets heard, the dangers of harmful speech, and the challenges of regulating platforms in a global media environment.

Host: Sean Illing (@SeanIlling)

Guest: Fara Dabhoiwala, historian and author of What Is Free Speech?

We’d love to hear from you. Email us at tga@voxmail.com or leave a voicemail at 1-800-214-5749. Your questions and feedback help us make a better show.

Watch full episodes of The Gray Area on YouTube.

Listen ad-free by becoming a Vox Member: http://vox.com/members
Learn more about your ad choices. Visit podcastchoices.com/adchoices

How much free speech is too much?

How much money is too much?

In today’s episode, political philosopher Ingrid Robeyns tells Sean that we need to cap the amount of wealth a person can accumulate. They talk about how extreme inequality affects democracy, the role of money in politics, and why limiting personal wealth benefits everyone, including the super rich.

Host: Sean Illing (⁠⁠@SeanIlling⁠⁠)

Guest: Ingrid Robeyns, ⁠⁠professor⁠⁠ and author of Limitarianism: ⁠⁠The Case Against Extreme Wealth⁠⁠

This episode originally aired in January 2024

We would love to hear from you. To tell us what you thought of this episode, email tga@voxmail.com or leave a voicemail at 1-800-214-5749. Your comments and questions help us make a better show.

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Imagine there's no billionaires

America has a hard time building stuff. Roads. Trains. Bridges. Housing. Everything takes seemingly forever. Meanwhile, China seems to have no trouble at all: high-speed rails, solar panels, electric cars, bridges, ports, all churned out at breakneck speed.

Why is that?

Sean's guest is Dan Wang, author of the new book Breakneck: China’s Quest to Engineer the Future. They discuss the policies and mindset that allow China to tackle remarkable feats of engineering, the advantages and drawbacks of America’s "lawyerly society," and what China and America must learn from each other.

Host: Sean Illing (@SeanIlling)

Guest: Dan Wang, author of Breakneck: China's Quest to Engineer the Future

This episode was made in partnership with Vox's Future Perfect team.

We would love to hear from you. To tell us what you thought! Email us at tga@voxmail.com or leave us a voicemail at 1-800-214-5749. We read and listen to everything, and might use your comments and questions in future episodes.

Listen to The Gray Area ad-free by becoming a Vox Member: vox.com/members and watch new episodes of The Gray Area on YouTube.
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America's lawyers vs. China's engineers

A loose movement of radical intellectuals is driving American politics. They’re called the “New Right,” and they share a basic hostility to American liberal democracy, a real desire to fundamentally overhaul it, and real influence in the White House. But why do they think that? How much influence do they really have? And what would a response to their rising prominence look like?

Today’s guest is Laura Field, a political theorist who’s spent a lot of time in the conservative intellectual world cataloging the wild world of far-right thinking for her book Furious Minds: The Making of the MAGA New Right. 

She speaks with guest host Zack Beauchamp, author of Vox newsletter On The Right, about why ordinary Americans should really, definitely, and absolutely care what a handful of thinkers are putting out on obscure Substacks and YouTube channels.

Host: Zack Beauchamp

Guest: Laura Field

We would love to hear from you. To tell us what we thought of this episode, email us at tga@voxmail.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
Learn more about your ad choices. Visit podcastchoices.com/adchoices

So, what exactly is the “New Right?”

Almost every tech platform is designed to grab and hold your attention, to keep you clicking, scrolling, and buying for as long as possible.

Sports gambling has become one of the clearest examples of this. The industry has created frictionless apps on your phone that let you bet on everything from March Madness to a pregame coin toss to who wins a minor league British dart tournament.

While betting has become easier — and arguably fun — the cost of these apps is much higher than the money that is won and lost on them.

Today’s guest is Jonathan D. Cohen, author of Losing Big: America's Reckless Bet on Sports Gambling. He and Sean discuss the rise of sports betting, why the industry targets young men in their advertising, the social costs of frictionless sports gambling, and how the industry could be improved.

Host: Sean Illing (@SeanIlling)

Guest: Jonathan D. Cohen, writer and author of Losing Big: America's Reckless Bet on Sports Gambling

We would love to hear from you. To tell us what we thought of this episode, email us at tga@voxmail.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
Learn more about your ad choices. Visit podcastchoices.com/adchoices

America is losing big on sports betting

My guest on this episode is Jesse Eisenberg — who you may know as Lex Luthor in Batman V. Superman, Mark Zuckerberg in The Social Network, or Daniel Atlas in the just-released Now You See Me 2.I was apprehensive about this interview. I haven't interviewed many movie stars. But this turned out to be one of the most natural, easy, and interesting conversations I've had for the show. Eisenberg is a cerebral Jewish writer who sees the world through the lens of sociolology and has a lot of trouble relaxing. So we had a lot to talk about, including:- Jewish humor and the dangers of assimilation- How it's different to write for the page than the stage- Whether Eisenberg has become happier as he's become more successful- What he learned backpacking through China- Why his family never takes vacations- How he turns the tables on fans who stop him in the street- Why he thinks it's easier to ask extremely personal questions of total strangers, and why it's worth doing- How his training as an actor helps him understand Donald TrumpAnd much more. So, so much more. 
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Jesse Eisenberg on Jewish humor, writing lessons, and interrogating strangers

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