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.

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Title Date published
Anniversary special: Rachel Maddow 2019-02-18
Andrew Sullivan and I work out our differences 2019-02-14
The core contradiction of American politics 2019-02-11
Leftists vs. liberals, with Elizabeth Bruenig 2019-02-07
The world according to Ralph Nader 2019-02-04
This conversation will change how you understand misogyny 2019-01-31
Ending the age of animal cruelty, with Bruce Friedrich 2019-01-28
Robert Sapolsky on the toxic intersection of poverty and stress 2019-01-24
Frances Lee on why bipartisanship is irrational 2019-01-21
Sean Decatur doesn’t see a free speech crisis on campus 2019-01-17
Cal Newport has an answer for digital burnout 2019-01-14
Eric Holder’s plan to save democracy 2019-01-10
Anil Dash on the biases of tech 2019-01-07
Jill Lepore on America’s two revolutions 2019-01-03
Best of: N.K. Jemisin 2018-12-31
Best-of: Bryan Stevenson 2018-12-27
Kara Swisher interviews me on the Future of Journalism (Live!) 2018-12-24
TED’s Chris Anderson on the lessons of listening 2018-12-20
Rep. Katie Porter on how capitalism is failing 2018-12-17
How Hasan Minhaj is reinventing political comedy 2018-12-13
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