When the Covid-19 pandemic arrived, and with it, the lockdowns of March 2020, I sat at home in Brooklyn Heights, alone, and watched as friends swiftly decamped to homes upstate, in the Hamptons and Connecticut, and beyond. One even moved to Miami. I have family in Colorado, and considered driving cross-country to be with them, but a part of me felt it was important, for whatever reason, to just stay put—not to flee the city, but to embrace it in one of its more precarious moments. For weeks, I listened to nonstop sirens wailing over the Brooklyn Bridge, along Cadman Plaza, and up and down the B.Q.E., and in them, I heard death. The banging of pots and pans at 7 p.m. each day to honor healthcare workers—heartwarming as the gesture was—felt to me more like a signal, a way for neighbors to say, “I’m still here. I’m still alive.” At times, the in-between silences felt almost deafening. There was so much grief and sadness in the stillness.

But in one particular neighbor and friend, the British-born philosopher Simon Critchley, I found solace. I’d met Critchley in the fall of 2019 (through Christian Madsbjerg, a mutual friend of ours), and soon he and I started a conversation—a series of questions, really—that would help sustain me through the various periods of lockdown, social distancing, and isolation. Throughout the first two years of the pandemic, around twice a month, we would meet up, typically at one of our favorite local bars, The Long Island Bar or Henry Public, and have long, rambling conversations about life and death, about hope and love and fear and grief and loss. Having a philosopher friend, and particularly Critchley, to consistently turn to and spend time with while wading through the early months (and then two-plus years) of pandemic muck was, and remains, a gift. He taught me—and a beautiful lesson it has been—that to philosophize is simply to question everything.

For the uninitiated (I suggest listening to him on our Time Sensitive podcast), Critchley is a force. A professor of philosophy at the New School and a board member of the Athens-based Onassis Foundation, he is the author of more than 25 books on subjects as far afield as soccer, David Bowie, suicide, humor, and Greek tragedy. To read Critchley is to time travel into the ancient past and into the distant future—to enter, Star Wars–like, into a philosophical galaxy far, far away that is at once highly intellectual and punk, uproariously funny and dryly (or is it wryly?) academic, casually conversational yet deeply studied, and incredibly entertaining. His books pair nicely with a cold pint of Guinness.

Now, with the world in some sort of re-emergence out of Covid, comes Critchley’s latest, the aptly titled Question Everything: A Stone Reader (Liveright), co-edited with New York Times opinion editor Peter Catapano. Featuring 100 essays from a wide-ranging cast, the book brings together pieces on everything from democracy to God, by a dozen or so celebrities and cultural figures, including the artist Ai Weiwei, the actor Cate Blanchett, and the jazz musician Sonny Rollins; writers such as the novelists Min Jin Lee and Elena Ferrante, and the filmmaker Errol Morris; and a bevy of academics, including the philosophy professors Iskra Fileva (University of Colorado), Sean D. Kelly (Harvard University), and Crispin Sartwell (Dickinson College). Perhaps subtly tying it all together are five texts by Critchley himself.

I recently met up with Critchley to discuss the book over a couple of beers—a Captain Lawrence ale for him, Old Speckled Hen for me—at one of our usual stomping grounds, Henry Public in Brooklyn’s Cobble Hill neighborhood. Our conversation, condensed and edited for clarity, follows.

What was the impetus for creating The Stone, your philosophy forum at The New York Times, in the first place? How did it evolve into this book?

It began with a conversation at a bar, on Smith Street in Brooklyn, a now-closed Irish pub, long gone. I had published The Book of Dead Philosophers in 2008, and that did well. A copy found its way to David Shipley, who was then the head opinion editor at The New York Times. He asked me to write an op-ed, which I did. Which came out on April Fools day in 2009. There was a clown-comedian, Randy Credico, who dressed up as Diogenes and protested in Albany about corruption in New York State. So I wrote a piece about that. Then David put me in touch with Peter Catapano. We immediately got along. He’s who I met at the bar. He was running the Times “website”—in quotation marks. The “real” New York Times then was the print newspaper, and they needed a “website,” but no one was really paying attention to what was happening on the website.

We had this idea for a philosophy column, and Shipley signed off on it. So The Stone began in 2010 with a piece titled “What Is a Philosopher?” We got, I don't know, 800,000, a million readers. It was crazy. And there was a controversy about it. So we had an audience.

Basically, we were functioning only online. The newspaper was the newspaper, and they weren’t really looking at what we did. We were able to do weird shit, like a three-part piece on Philip K. Dick—whatever we liked, really. And length wasn’t an issue. We weren’t restricted by the opinion page. Then, when the Times went over to what it is now, becoming a digital megalith, initially—in 2014, 2015—they were obsessed with “community.” They wanted to build up online communities of readers. And we already had that in place. But the more the Times became a digital interface, it became harder and harder to get our stuff on Page One. We had amazing publicity for years and years, and we proved that if it’s done without jargon, on topics that people care about, and in a language they understand, there’s a huge audience for philosophy.

This is the second book from The Stone, right?

Third book. There was The Stone Reader: Modern Philosophy in 133 Arguments in 2015. And then Modern Ethics in 77 Arguments in 2017. And then this one, which covers the period from 2015 to 2021. A lot of it is much more thematic. It’s got thirteen sections with these huge questions: “What Is It Like to Be a Woman?” “Why Does Art Matter?” The last section is: “Now What?”

I read the book as a sort of ramp-up to, and then a processing of, the pandemic—it shares some qualities with our At a Distance book.

It does, yeah.

At its heart, Question Everything is really about these deep, profound links between ancient times and the present—links that seemed to have been even more heightened in the time of Trump and then of Covid.

Yeah, we seem to have discovered that the idea of something archaic is actually revived. We’re ancient in the sense that the philosophy is roughly three thousand years old. None of the major questions have been resolved, and that’s the point. So the Question Everything idea is, basically: Philosophy is the movement into perplexity, into questioning.

I have to bring up “The Happiest Man I Ever Met” here. Such an incredible journey and piece. To spend three days in Greece’s revered “Holy Mountain” monastery, and to effectively gauge what it’s like to be a monk…

The freedom I had was amazing. You pinch yourself sometimes. But I did these eight pieces [for the Times] from Athens. I knew I was going to write some pieces. I didn’t know what they were going to be about.

I wrote this piece about going to Mount Athos, the monastery, and meeting this man, Father Ioanikios, who took me around Mount Athos in his Toyota truck, talking to me about grace and the energy of God. He had been an engineering student at N.Y.U. in the 1970s—

Partied at Studio 54.

Partied at Studio 54. Very handsome guy. And I listened to him sing in the choir for eleven, twelve hours in those three days.

So, by that point, a lot of the work that I was doing was more and more observational. I was almost reporting, in a way. I was trying to get away from thinking things; I was trying to observe situations and describe them.

Almost journalism.

You’d think it was journalism. Everything was ferociously edited by Peter Catapano. Every word in the book is the consequence of one fight or another.

There are these two other Times pieces you wrote, which are also in the book, that I wanted to bring up: “Abandon (Nearly) All Hope” and “To Philosophize Is to Learn How to Die.”

So “Abandon (Nearly) All Hope” is an attack on hope, and an attack on the moral hypocrisy of hope peddlers, and how what we should have is, rather than hope, courage.

It’s interesting that our era of hope—the Obama years, basically—was followed by Trump and a pandemic.

Right. The audacity and mendacity of hope. The pandemic, of course, was a very philosophical moment. So “To Philosophize Is to Learn How to Die” is a kind of meditation on melancholy, misery, and mortality as what really makes us human. The pandemic was very good for philosophy because everybody was at home, feeling a bit sad, and forced to confront themselves. At that point, they had to become philosophers.

Much of what you write is populist to a degree. Like your book Bowie, essentially about the philosophy of David Bowie, but also that great Times op-ed you wrote about Bowie [“What Would David Bowie Do?”] last year. I can’t really think of a more populist way of entering the philosophical realm than through a figure like Bowie.

Absolutely. He was a philosopher, a deep thinker. The most important artist in any medium of the last half century, in my opinion. I think that’s now becoming clearer and clearer. When you look at that Moonage Daydream movie that came out, you see what Bowie actually thought about things like the Internet. He saw what was happening and the way things were going to develop and change. And he became a pop star by accident. He wouldn’t have been a pop star now.

But the dystopia of that period in particular: The Bowie piece was written January 1, 2021. And I got really heavy edits back. And I had a deadline—it was going to go in the newspaper. I finished it around noon on January 6. And I thought, Okay, it’s gone, I’m exhausted. I was up since 5 in the morning. And then I thought, I’ll turn on the television because I want to see this ratification of the election. Then I watched January 6 happen. So yeah, it was a bit resonant.

Beyond your own essays, there are so many incredible voices in the book. It’s a chorus.

Cate Blanchett!

I particularly enjoyed the Min Jin Lee essay [“Breaking My Own Silence”]. It’s extraordinary.

Oh, good.

And Sonny Rollins’s “Art Never Dies.”

Yeah, fantastic piece. When has Sonny Rollins ever been in a philosophy book? Or Cate Blanchett?

So, to finish: Question Everything, if that’s the title of this moment, where do you see the conversation going next?

Question nothing! [Laughs] I don’t know. The reason for the title is nice: The book is dedicated to two Garys. There was this guy, Gary Gutting, who I was a colleague with at Notre Dame for a semester. Lovely man, very principled, Catholic philosopher. And he wrote regularly for us as a voice of Midwest liberal conscience. Brilliant man. He died, sadly. Then there’s the other Gary, Gary Leib. He was in college with the Talking Heads at RISD in that period, and played in bands. He did a one-minute animation for us in 2015 to help promote the first book. In it, he had this line, “question everything,” in plasticine. So we thought, in his honor, we’d use that as a title.

The point is not to answer anything. Philosophy asks questions: What is justice? We don’t know what justice is. The issue is knowing which question to ask. And then to use that questioning as a way of dismantling the way certain people would say, “Justice is X, justice is Y. Justice is the rule of the rich over the poor. Justice is what’s in my interest.” Or whatever it might be. Or when people talk in this vague way about “social justice”—what’s actually meant by that? Justice has to be a question, not an answer.

Philosophy is about raising questions that won’t go away. The point is to be happy with that.