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The Gray Area with Sean Illing

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. N

Can prediction markets be good for society?
Oct 2026
0:00 / 48:08
Our gender divide
Oct 2026 · 3 books
0:00 / 46:44
Cover of Generation Uncoupled: A Generation Apart: America's New Gender Divide and the Crisis of Human Connection
Generation Uncoupled: A Generation Apart: America's New Gender Divide and the Crisis of Human Connection
Daniel Cox
danielle has just written a new book titled generation uncoupled america's new gender divide and the crisis of human connection ▶ tap to play from here
Cover of Rethinking Sex: A Provocation
Rethinking Sex: A Provocation
Christine Emba
some of that was drawn from your you know truly excellent book rethinking sex right ▶ tap to play from here
Cover of The Second Coming
The Second Coming
Carter Sherman
from the journalist carter sherman's book the second coming ▶ tap to play from here
The death row assembly line
Oct 2026 · 1 book
0:00 / 58:34
Cover of To Catch a Devil
To Catch a Devil
Pamela Colloff
she has a new book out called to catch a devil ▶ tap to play from here
Is it bad to want to be rich?
Oct 2026 · 3 books
0:00 / 50:36
Cover of Why It's Okay to Want to Be Rich
Why It's Okay to Want to Be Rich
Jason Brennan
author of a book with an unforgettable title why it's okay to want to be rich ▶ tap to play from here
Cover of The Wealth of Nations
The Wealth of Nations
Adam Smith
adam smith wrote this book called the wealth of nations in seventeen seventy six ▶ tap to play from here
Cover of Glass Houses: Choosing Grace in a Judgmental World
Glass Houses: Choosing Grace in a Judgmental World
Jason Brennan
a book coming out in about a month that's called uh uh glass houses choosing grace in a judgmental world ▶ tap to play from here
Why does killing a bug feel wrong?
Oct 2026
0:00 / 34:45
How trauma became a status symbol
Sep 2026 · 4 books
0:00 / 41:12
Cover of Traumatized: The New Politics of Public Suffering
Traumatized: The New Politics of Public Suffering
Catherine Liu
scathing new book traumatized the new politics of public suffering ▶ tap to play from here
Cover of The Making of the English Working Class
The Making of the English Working Class
E. P. Thompson
e p thompson tries to paint a port portrait of that in the invention of the english working class ▶ tap to play from here
Cover of Capital
Capital
Karl Marx
you have to go into e p thompson and marks to get an account of what it was like to be in in the factories ▶ tap to play from here
Cover of The Cult of Smart: Education and Our Degrading Democracy
The Cult of Smart: Education and Our Degrading Democracy
Freddie deBoer
i think you're talking about freddie deborah's book i think on um mental illness as identity ▶ tap to play from here
Inside the world of cash advance apps
Sep 2026
0:00 / 41:08
This is how you rule the world
Sep 2026 · 1 book
0:00 / 58:31
Cover of How to Rule the World: An Education in Power at Stanford University
How to Rule the World: An Education in Power at Stanford University
Theo Baker
theew's book is called how to rule the world and the title isn't a metaphor ▶ tap to play from here
Is starting a family becoming impossible?
Sep 2026 · 1 book
0:00 / 58:01
Cover of Inconceivable: The Impossibility of Family in an Age of Uncertainty
Inconceivable: The Impossibility of Family in an Age of Uncertainty
Anna Louis Sussman
her new book inconceivable the impossibility of family in an age of uncertainty goes deep reporting with insight and fantastic stories on the web of factors influencing the new turn away from childbearing ▶ tap to play from here
The millennial midlife crisis
Sep 2026 · 2 books
0:00 / 49:55
Cover of But You're Still So Young
But You're Still So Young
Kayleen Schaeffer
there's this book that i read when i was in my early 30s ▶ tap to play from here
LA
Life After Ambition, a Good Enough Memoir
Emile Niazi
it's called life after ambition a good enough memoir ▶ tap to play from here
How to be less neurotic
Sep 2026 · 2 books
0:00 / 39:35
Cover of Me, But Better: The Science and Promise of Personality Change
Me, But Better: The Science and Promise of Personality Change
Olga Kazan
author of me but better the scientist and promise of personality change ▶ tap to play from here
Cover of 10% Happier
10% Happier
Dan Harris
one of the books that i read kind of in in reporting out my book is 10 happier ▶ tap to play from here
Your body wasn’t built for a desk
Sep 2026 · 2 books
0:00 / 44:19
Cover of Body Electric
Body Electric
Manoush Zomorodi
a benoiticious new book body electric about what a life of sitting and staring at screens is doing to us ▶ tap to play from here
Cover of The Anxious Generation
The Anxious Generation
Jonathan Haidt
we know john height's book the anxious generation has been on the bestseller list for years now ▶ tap to play from here
Why we want to believe in aliens
Aug 2026 · 1 book
0:00 / 51:16
Cover of We Want to Believe: How Aliens Went Mainstream and Why It Matters
We Want to Believe: How Aliens Went Mainstream and Why It Matters
Adam Kirsch
he's a senior editor at the atlantic and author of we want to believe how aliens went mainstream and why it matters ▶ tap to play from here
Straight dating isn’t broken
Aug 2026 · 1 book
0:00 / 42:30
Cover of Men Are from Mars, Women Are from Venus
Men Are from Mars, Women Are from Venus
John Gray
men are from mars women are from venus was a bestseller for a reason ▶ tap to play from here
Kidneys for sale
Aug 2026 · 1 book
0:00 / 49:29
Cover of Moral Economics
Moral Economics
Al Roth
his new book is called moral economics ▶ tap to play from here
How memory changes you
Aug 2026 · 1 book
0:00 / 59:17
Cover of Why We Remember
Why We Remember
Sharon Ranganath
my guest today is sharon ranganov a neuroscientist and author of a book called why we remember ▶ tap to play from here
Freud was right about one thing
Aug 2026 · 1 book
0:00 / 58:48
Cover of The Only Cure: Freud and the Neuroscience of Mental Healing
The Only Cure: Freud and the Neuroscience of Mental Healing
Mark Solms
he's a neuropsychologist and the author of the only cure freud and the neuroscience of mental healing ▶ tap to play from here
Why straight dating feels bleak
Aug 2026 · 1 book
0:00 / 57:48
Cover of Disposable
Disposable
Sarah Jones
and my first book disposable is out now from avid reader press ▶ tap to play from here
We’re postliterate
Aug 2026 · 8 books
0:00 / 51:41
Cover of The Boxcar Children
The Boxcar Children
Gertrude Chandler Warner
my sisters were always excited to to talk about the boxcar children with me and everything like that ▶ tap to play from here
Cover of Orality and Literacy
Orality and Literacy
Walter Ong
this is a story that walter ong wrote about in his book orality and literacy ▶ tap to play from here
Cover of The Odyssey
The Odyssey
Homer
i mean i think everyone's talking about the odyssey right now ▶ tap to play from here
Cover of The Grapes of Wrath
The Grapes of Wrath
John Steinbeck
in ap english we were reading grapes of wrath ▶ tap to play from here
Cover of Crime and Punishment
Crime and Punishment
Fyodor Dostoevsky
should we really be judging people for reading the hunger games instead of crime and punishment ▶ tap to play from here
Cover of The Hunger Games
The Hunger Games
Suzanne Collins
should we really be judging people for reading the hunger games instead of crime and punishment ▶ tap to play from here
Cover of Phaedrus
Phaedrus
Plato
this work by plato the phaedrus ▶ tap to play from here
Cover of The Iliad
The Iliad
Homer
who could memorize the iliad or the odyssey now ▶ tap to play from here
What does a parent owe their child?
Aug 2026
0:00 / 27:47
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