Andrew Sullivan on Braving New Intellectual Journeys (Ep. 129)

Why are so few intellectuals comfortable with life out on a limb?

Upon learning he was HIV positive in 1993, Andrew Sullivan began writing more than he ever had before. Believing that he didn’t have long to live, he wanted to leave behind a book detailing his best argument for refocusing the gay rights movement on marriage equality and military service. Three decades later and Sullivan has not only lived to see the book published, but also seen the ideas in it gain legal and cultural acceptance. This, along with the fact that the pace and influence of his writing has continued apace, qualifies him in Tyler’s estimation as the most influential public intellectual of his generation.

Andrew joined Tyler to discuss the role of the AIDs epidemic in achieving marriage equality, the difficulty of devoutness in everyday life, why public intellectuals often lack courage, how being a gay man helps him access perspectives he otherwise wouldn’t, how drugs influence his ideas, the reasons why he’s a passionate defender of SATs and IQ tests, what Niall Ferguson and Boris Johnson were like as fellow undergraduates, what Americans get wrong about British politics, why so few people share his admiration for Margaret Thatcher, why Bowie was so special, why Airplane! is his favorite movie, what Oakeshottian conservatism offers us today, whether wokeism has a positive influence globally, why he someday hopes to glower at the sea from in the west of Ireland, and more.

Listen to the full conversation

You can also watch a video of the conversation here.

Read the full transcript

COWEN: Hello everyone, and welcome back to Conversations with Tyler. Today I’m here with Andrew Sullivan. Andrew needs no introduction, but it is worth noting, he has a new book that just came out called Out on a Limb: Selected Writing, 1989–2021. I would say, if you would like one single all-purpose introduction to Andrew Sullivan, this is the book.

Andrew, welcome.

SULLIVAN: Thank you, Tyler. I’m thrilled to be here, and that’s correct: the whole point of doing this book was to say, OK, you hear all this stuff about me — well, here it is. This is the actual bulk of the work. I hope people dip in and out of it. It’s not supposed to be a first-page-to-last-page read, but it’s an attempt to just clarify a little bit what I’ve been writing for the last 30 years.

I’m hoping to show that there is a consistency to it. I’m not entirely consistent, obviously, because I’ve changed and the world has changed; but also as a way to just show the history of the last 30 years, because the thing is arranged chronologically. That’s the idea of the book — if you just give a good intro to my various obsessions, passions, beliefs, ideas, and arguments over the last 30 years.

On the Andrew Sullivan production function

COWEN: Now since I’ve nominated you as the most influential public intellectual of our generation, I would like to start with some questions about the Andrew Sullivan production function.

SULLIVAN: Okey doke.

COWEN: So let’s go back in time. At some point you learn you’re HIV/AIDS-positive. How did that possible risk of premature death affect your productivity over the longer run — because you have done an enormous amount, as is shown in the book?

SULLIVAN: It obviously didn’t. In fact, it propelled me to write more.

COWEN: How so?

SULLIVAN: Well, for example, Virtually Normal — it’s a book I wrote in 1995, which was basically the first book laying out the arguments for overhauling the gay rights movement and making marriage equality and military service its central features — I would not have written had I not realized I had, or thought I had, maybe a few years to live. I decided that if I was going to die in my mid-30s, which is what everyone seemed to think would happen even though they were a little optimistic about it at the time — but I wasn’t — I wanted to leave something behind.

I wanted to leave behind my best argument for this simple civil rights reform. They allowed me to take leave at the New Republic in 1994. I seroconverted in 1993. In fact, the foreword of the book has a little date under it, which is the date of my seroconversion — so that I put in the book a clear sign of why I was doing that. In other words, I felt I didn’t have much time left, and I needed to do everything I could.

Then, also, I just also believed and felt that this was an enormous story, this extraordinary plague that devastated a small community, really, in the context of a very large community that really wasn’t that affected, and how that changed a lot of people’s minds and hearts and how it was the thing that propelled us, in a way, to make the civil rights arguments of the next couple of decades. I don’t believe that without AIDS, we would have marriage equality today. I just don’t.

COWEN: If we fast forward to today, let’s say you were to learn that you had only four years left to live, but most of it in healthy mind and body — what is it you would do right now, knowing that?

SULLIVAN: That’s a really good question. The good news is that back when it happened to me before, I realized that I was doing the work I really wanted to be doing. It was very clarifying, editing the New Republic.

Right now, I love to do what I’m doing, but I will be honest and say I think I would take time to spend more time with my friends and my family. I would try and travel some more because I haven’t really done enough of that, even though it’s a little hard right now. I’d probably up my intake of mushrooms; I think I would try and gain some perspective on mortality. I think I would become probably much more devout than I currently am. But these are suppositions.

You kind of learn —

COWEN: Why not become more devout now?

SULLIVAN: I’m a human being, and death is the ultimate reminder of ultimate reality. We can push that out of our heads all the time and carry on quite normally, but the prospect of dying really does concentrate not just the mind but the soul, and you have to figure that out.

Of course, I should feel those things now; I should — we all should — and that’s the paradox of this. We know that there’s a difference between a life of doing and a life of being, and sometimes because our default-mode network kicks in, as it were, we spend much too much time doing things than being something — and so that’s the paradox.

We know that there’s a difference between a life of doing and a life of being, and sometimes because our default-mode network kicks in, as it were, we spend much too much time doing things than being something. I know there were moments in my life when, presented with mortality, I got a very crisper sense of God, of my own life and the universe. Then, over time, you just get caught up in the mundane and the everyday and the frustrations, and you lose that perspective.

I know there were moments in my life when, presented with mortality, I got a very crisper sense of God, of my own life and the universe. Then, over time, you just get caught up in the mundane and the everyday and the frustrations, and you lose that perspective.

COWEN: Now you’ve taken quite a few intellectual risks in your career. If you look at our intellectuals and public intellectuals as a whole, what do you think is the most fundamental reason why they lack courage?

SULLIVAN: These are good questions, Tyler.

I think I’ve been struck over the last few years, specifically, at how many journalists, especially, or public intellectuals are very much members of their own class and are extremely concerned, perhaps more than ever, what their own peers think about them — and so are actually very, very vulnerable to social pressure. I think that means you don’t want to take risks if you want to have a good career in intellectual journalism. You don’t want to alienate your peers, and increasingly your peers are all taken from a pretty narrow socioeconomic base, who hold very similar opinions — and that’s become truer over the last 20 years.

The career and psychological and social costs of going “out on a limb” are quite considerable. I think I am lucky, to some extent, to have a life that’s really not socializing with all those peers. My friends are a very eclectic bunch of people and almost none of them — a few of them are, but a lot of them are not — in journalism or in public intellectual life at all.

COWEN: What accounts for that? What variable in you, in them, has led that to be the equilibrium?

SULLIVAN: Part of it is being gay, because you inevitably develop a social network that is independent of your professional network because that’s how you socialize in many ways, and from that, you generate a different kind of perspective.

Also, I don’t know, I just get bored and irritated by my peers. I’d much rather listen and talk to someone with a completely different perspective. My best friend plays jazz piano, for example, and we talk about everything. We talk about politics, but he comes from a place where I can sit down with him and say, “What do you think about this? You haven’t processed this immeasurably, but what do you think?” Most ordinary people outside of that circle will ask all sorts of very straightforward questions that my peers haven’t even thought about, and will see things from a different perspective.

I also think the fact that I come from basically a non-college-educated family, so that I grew up with people who didn’t have those esoterical, those academic skills, and certainly not the social skills to belong in the upper-middle classes —

COWEN: Same with me, I might add.

SULLIVAN: Well, and so you get used to real conversations about people, and you don’t mistake credentials for intelligence. You realize that people outside of the system may be more perceptive about what’s going wrong with it than people buried within it. I honestly find life more interesting the more variety of people you get to know and meet. And that means from all sorts of different ways of life.

The good thing about being gay, I will tell you, is that that happens more often than if you’re straight — because it’s a great equalizer. You are more likely to come across someone who really is from a totally different socioeconomic group than you are through sexual and romantic attraction, and indeed the existence of this subterranean world that is taken from every other particular class and structure, than you would if you just grew up in a straight world where you didn’t have to question these things and where your social life was bound up with your work or with your professional peers.

The idea for me of dating someone in my office would be absolutely bizarre, for example. I can’t believe all these straight people that just look around them and say, “Oh, let’s get married.” Whereas gay people have this immense social system that can throw up anybody from any way of life into your social circle.

The idea for me of dating someone in my office would be absolutely bizarre, for example. I can’t believe all these straight people that just look around them and say, “Oh, let’s get married.” Whereas gay people have this immense social system that can throw up anybody from any way of life into your social circle.

COWEN: Your nongay friends you think are in some ways more conformist than your gay friends, issues of sex aside? There’s a sense in which simply —

SULLIVAN: No, because my nongay friends — it’s also true that my nongay friends who are not part of the elite are also similar to that. They have a different perspective.

But yes, I find them to be often more questioning, more curious, and more capable of asking basic questions and not taking things for granted than many of my peers, which makes them better, which is why I think journalists are better off coming from ordinary people — like working-class journalists who knew people, who knew reality, weren’t caught up in ideology or orthodoxy or have any interest in their social peers, and were just interested in getting to a story or breaking a story or finding something out, regardless of the consequences. That’s the kind of journalism I like, and finding a way to make yourself popular among certain elites is just not something I ever wanted to do.

I’ll tell you this: I’m also just not that big a socializing person. I tend to have friends that are very individual, one on one. I tend to hang out with small groups of people. I don’t have parties; I don’t go to parties. I’m just not a clubbable person. I’ve never easily fit in to any institution that I belong to, and that’s just my personality.

COWEN: Putting aside issues of sex, but how do your conversations with your gay friends differ from those with your nongay friends?

SULLIVAN: We are more candid with each other, I think. We’re certainly more candid about affairs of the heart. There’s a frankness and rudeness and sense of humor that is hard to explain outside of its particular context.

But I don’t want to give you the impression that my nongay friends are somehow in some boring category; they’re not at all. I’m talking more about my straight peers within my profession rather than my regular nongay friends in real life.

COWEN: Taking a hetero person such as myself, if I want more of this element at the margin that you have with your gay friends, what’s the needed input to produce that?

SULLIVAN: I think it’s going to places you wouldn’t otherwise go, meeting people who are new, finding a way outside your own circle of friends, your own socioeconomic status. One thing that I was talking to Charles Murray about, actually, was how he does his poker game that he plays with just regular folks in a casino. It’s a regular thing that he does. None of them are from his way of life. But it’s a great way to get in touch with how people genuinely feel outside of the chattering classes. And I think that’s the gain.

I’m not helping you very much here, am I, with the — I don’t want to give the impression gay people are somehow more fun, or — I’m just saying you’re more likely to randomly come across someone who’s not part of your scene or your class or your race, for that matter, as a gay person, simply because as a gay man, especially, the sexual and social dynamics are utterly independent of professional, intellectual, or ideological dynamics. And so, essentially, you become friends with someone because you’ve seen them a lot at a gym or a bar or at a restaurant, and it just becomes that; it doesn’t become, What did you do? What do you do? How do you make a living? And so on and so forth.

On self-medication

COWEN: You mentioned before mushrooms. How do you think that self-medication — whether it be mushrooms, marijuana, testosterone, something else — influences the actual content of your ideas?

SULLIVAN: Of course it influences them. Let me give you an example. I’m a daily weed smoker. I have been since I was 36; I was a late bloomer on this. For me, what that does — I never work under the influence of any substance; this is always outside of the work hours. I’m not crazy. I don’t really drink anything. Weed will happen at the end of the day. What I find that marijuana does, and to some extent — mushrooms definitely do, meditation does as well — is that they suppress the ego. They weaken the ego.

If you write something, as I often do, and finish it (or a first draft) and then smoke something and then go and take a walk, and just let my ego disappear a little bit and let me look at what I’ve personally done as if I were looking at something someone else had done, with that same kind of dispassion, then you’re like, “I got that wrong.” Or “why did I miss that?” Or “that’s stupid.” Or “maybe if I turned the thing around — ”

You’re less attached to your own pride. Your mind is taken out of its normal rut.

COWEN: So you change your mind more?

SULLIVAN: Yes. Yes! Also true with something like MDMA. I remember, for example, writing Virtually Normal, which was this very tightly argued, cerebral book. Then, after I’d finished the gut of it, I went to celebrate with some friends. We went out dancing; I did some MDMA. In the middle of the dance floor, I was like, “You know what? I haven’t put in this book at all why I care about this subject, why it matters to me. I’m being too abstract here.” That’s when I went back and then I wrote the introduction and then the epilogue, which were much less intellectual and more experiential. They are the most popular parts of the book.

You allow yourself to realize you might have made a mistake. You might have made just simply a factual error, which happens to everybody and you wake up in the middle of the night, or you just realize maybe that judgment you became too attached to because you were too proud to let go of it. Taking a moment to take your pride out of it and take your ego out of it gives you some possibility after hours of reassessing your work.

Also, the thing that happened with blogging was that because you were constantly writing, you had to constantly account for changes in mood, in argument, and in your opinions — because it charts you day by day, hour by hour. That was another thing that got me to shift my opinions.

The testosterone, I think, does give you a certain amount of energy, and I have to be careful because it’s every two weeks — it’s only 1 cc; it’s not a massive amount — but the next two days I have to be careful I don’t pop off on something. It’s funny: my colleague, Chris Bodenner, used to tell when I’d just taken a shot because somehow I just fire off this incredibly passionate rant or something. I have to be aware of that too.

We are a function of everything. I could just as well say that eating, as I used to, sugar and cookies all morning as I wrote The Dish gave me this wiry focus, but we’re all a mix of chemicals.

COWEN: What kind of mental process do you use to try to decide if a new idea you have is just the result of bias from substances? Or do you just think, “Well, some of them will be biased, but it’s more important to innovate so I’m going to double down on this.” How do those thoughts go?

SULLIVAN: I literally have a little book called Highdeas, which is ideas I’ve had when I’m high. And I write them down — but then I make sure I look at them totally sober. I would say about three-quarters of them are nuts and I throw them out, and a quarter —

COWEN: This is the book we want you to publish in your last four years.

SULLIVAN: [laughs] — good highdeas, things I can’t really say or think about.

But I just let my mind wander. I’m just a curious person. I love thinking about stuff. I think my mind can go down a rabbit hole. This was part of the problem with me for a long time: I had terrible insomnia until I found cannabis in my late 30s. Some of us have minds that just won’t stop and it can be an ordeal.

It’s not for lack of — I’m not going to not think while I’m on weed or even when I’m on MDMA. I find, for example, on MDA mushrooms, it’s all theology for me. It’s all about God. It’s all about the relationship between the Trinity, the possibility of the Incarnation — these things are what I become obsessed with when I’m really on mushrooms or MDMA or the hallucinogens. Yes, it becomes all about Christianity in a very weird way.

COWEN: You know it was Herodotus who first suggested the idea of examining all ideas, both when sober and when drunk —

SULLIVAN: [laughs] Oh really.

COWEN: — to see if they were good.

SULLIVAN: It helps, because the more ways you can look at a topic, perhaps the more you’ll understand it, to be honest; but I think the main thing is ego. The main thing is the ego bias. We don’t want to be wrong, and certainly, if we’ve taken a position, it’s really hard for us to accept that we screwed up.

COWEN: Given that you didn’t come from a fancy background, who first noticed your talent, and how?

SULLIVAN: It was kind of a shock. When I was in elementary school — and this will tell you a certain amount about me — there was an exam that they sit, that you can sit for back in those days, called the eleven-plus, which was an IQ test essentially. I was just a kid in elementary school, and I was about to graduate and go to high school. They set this test and then my head teacher brought my parents in and I thought I was in trouble. It turned out I had the highest score in the county or something.

That was when I was told I was very smart. I wasn’t really aware of it until then. I got sent to this super magnet school, which was wonderful, and for people from all backgrounds who just were over certain level of IQ — a kind of Stuyvesant, a kind of magnet school.

And then within the first month, they graded everyone on all the topics and put the list of 1 to 30 in the class on the wall. And I was number one, which was another huge shock to me. So that’s how I found out. I was not really aware that I was that bright, but the system found me and this is why I’m a pretty passionate defender of SATs and IQ tests in general, to find kids who otherwise would be missed, especially kids from poorer backgrounds who have native ability but haven’t had a chance to show that and whose parents could not have afforded — My parents could not have afforded to send me to any school where we’d have to pay.

So that was how it happened.

On Niall Ferguson, Boris Johnson, and British politics

COWEN: Now, as an undergraduate, you knew and were friends with Niall Ferguson. What was he like back then?

SULLIVAN: Pretty much the same. We were a little wilder, to be honest. We were a little brassier and a little more interested in just comedy. We published a little ramshackle magazine that poked fun at the toffs, at the Etonians. We both thought of ourselves a little bit as what we’d call grammar school boys, who weren’t part of the elite, but we got in because of our brains.

We were a little contemptuous of one of our peers, for example: Boris Johnson, who was also there at the same time. This is what happens in England. It’s a very close — it’s a very small elite, in a way. I also went to high school — sat next to — Keir Starmer for six years, who’s now the leader of the opposition.

So it’s amazing that in my own education, just by chance, I became friends with the current leader of the opposition and the prime minister.

COWEN: Given that you knew him then, what insight do you have into the Boris Johnson administration that the rest of us would not?

SULLIVAN: He’s a charmer and a liar and hilarious.

COWEN: On purpose, hilarious.

SULLIVAN: Yes. He was an Etonian who showed up — and all of the Etonians (people who came from Eton, the highest fancy school in Britain) —

Unlike the other Etonians who came to Oxford and decided, “Well, we’ve got to downplay this, we’ve got to be — got to wear regular clothes and alter our accent” — no, Boris came and said, “Instead of fighting it, I’m going to just turn into a caricature of an upper-class twit.” Have you ever seen the Monty Python sketch of the — ? One of those, but did so with such a knowing irony that we all kind of got the joke.

It’s the same act that he’s doing now, and I, for one, at the time at Oxford, because we were both in the Oxford Union together, which was the debating society where you got elected or whatever. I was elected president in my second year and he had a hard time, but I was very much on his side because I just thought he was a talent, and I found him funny and I could forgive him for anything, really.

I think that’s why, maybe, having known that side of Boris and not being intimately aware — as my peers in England were — of all his shenanigans, of all his lies, of all his corners cut, of all the betrayals that he committed, I didn’t see any of that and experience it. When I went back to England and talked to all my peers about him, they were so full of bitterness that they have begun, I think, to forget his basic charm and that power.

I saw that at Oxford. It’s the same thing now, and it’s why he’s a very successful politician.

COWEN: More generally, what is it that intelligent, educated Americans get wrong about British politics?

SULLIVAN: Well, they’re wrong to think that it’s somehow a more elevated discourse. It can be at times, but it’s just as raucous as here.

I think Brexit has been terribly misunderstood by Americans because they conflated it, for understandable reasons, with Trump, and they conflated Boris Johnson with Trump. Simply not the case. If you had had a less crazy — Boris is not crazy at all; he’s a very smart person and he’s also not, like Trump, a complete outsider. He’s the insider’s insider. Editor of The Spectator, Oxford, Eton, mayor of London: these are not outsider positions. And therefore dismiss it, and don’t really understand that in fact, I think the Tories have developed a very canny strategy to represent the voices and feelings of those who feel they’re left behind without abandoning an important segment of the elite. And that’s the role of the Tory party historically — it’s been to co-opt populism for elitism, as it were to prevent revolution by co-opting.

I think what Boris has done, in fact, and one of the things you’ll notice in Britain, is that the far-right parties that were gaining strength have collapsed and the Tories basically own the entire right-of-center vote. Whereas the Left is split between Liberal Democrats and the Labour Party and the Greens in a way that gives Boris a constant advantage. That, I think, is not very well understood.

COWEN: Do you think the United Kingdom will split up in the next few decades, as we know it?

SULLIVAN: Probably. I wrote a piece like 20 years ago — I read it when I was going through the book, reading things to see if I would include it in the book — where I basically predicted that I can’t see Scotland being part of the UK past another 20 years. And that was about 20 years ago.

COWEN: But don’t they want to leave and keep the pound and the Queen and everything else, and just say “buzz off” to the English? Where can they go, really? Trade, language . . . ?

SULLIVAN: I agree with you. Every time they’ve come up to this decision, it looks like you’re going to pass it and they always pull back because, in fact, the arguments for Scottish independence are incredibly weak.

First of all, the EU would not recognize it. The EU is not going to have Scotland as an independent state because they’d have to do it with Catalonia and other elements in Europe which the Spanish, for example, would veto.

I don’t think they have a chance to get back in the EU, even though they have these old — Scots: you go back to the 16th and 17th centuries, the Scots were always allied with the Europeans against the English. The French, primarily, against English. Maybe — I don’t know. I do think that Northern Ireland has been effectively turned into non-UK by the trade barrier in the Irish Sea which Boris negotiated. I think that Northern Ireland has definitely taken a step away from being fully in the union the way that Scotland and Wales are.

COWEN: Whether or not you agree with it, but what is the most convincing version of British pessimism? Is it John Gray? Is it Roger Scruton? Is it Fitzjames Stephen? Someone else? Is it you? Who or what is it? Because you are mostly optimistic. Who’s the pessimist where you are tempted to cross over to the dark side?

SULLIVAN: [laughs] Maybe someone like Peter Hitchens or Douglas Murray, who have a really bleak understanding of what’s happening in Europe with the Muslim population, and also a sense that traditional classical liberalism in Britain is really under siege.

[horn sounds] Sorry. That’s a ferry boat blasting from the deck; excuse me —

COWEN: Don’t worry; we’ve had trains cross through our episodes.

SULLIVAN: These are good questions, Tyler.

So I think that’s what I would say to that.

COWEN: The Muslim immigration to Britain seems to have gone acceptably well, right?

SULLIVAN: I think that there are parts of England, northern England particularly, which have had some issues with not full integration: really some separatist entities. Bradford, I think, would be one of them. And in which there have been really ugly child-grooming practices and ways in which the Muslim community in those areas — which came from very rural, backward areas of Pakistan — they’re weren’t quite ready for modern liberal democracy.

There’s some element in which that works, but in general, when I go to England I do think that it’s pretty successful multiracially. But then I think America is too, because I have a slightly lower expectation, I think, of human nature than most people do — but in general the English and the Americans: pretty easygoing about this. You go to London and it’s pretty easygoing.

What they were responding to, I think, is the speed of change in which — one of the saddest things my brother ever said to me when I was over there a few years ago, was talking about London — and he said to me, “Well, it’s not our capital city anymore, is it?” It really struck me that he felt that London was a different country now, that it was an internationalist, global playground as opposed to England’s and Britain’s capital city.

When you look at the demographics, you see that 40 percent of Londoners were not born in the United Kingdom. Now in New York, fine, that’s always been the case. It’s a big immigration entrepôt. But that’s never happened to England before. If you go to London, it’s very hard to hear an English accent or an English person in any service industry. It’s quite remarkable. And of course in some ways, that’s a huge advertisement for London. It’s the place where every other European wants to go live; it’s a place where people all over the world want to live. It’s a fantastic city.

But from the perspective of the coherence of England, I think it happened a little too fast and it was a little too much, and that’s the adjustment.

On women in politics

COWEN: Why is there so much residual British hatred of Margaret Thatcher — so to call her Maggie the Milk Snatcher? You’ll still hear that. Like, who cares? How long ago was that? The milk, whatever. What is it about her that so set off her enemies?

SULLIVAN: It’s funny because when I was a kid, I always used to fight with [Keir] Starmer all the time about Thatcher in the ’70s, and the passions were intense. I think the thing is that she changed Britain and she did it without a great deal of emollience, as it were. She just did it.

And she did it in a way that profoundly shifted Britain from a socialistic to a much more capitalistic country. From what I felt was an incredibly stultified, class-based country to a much more entrepreneurial and dynamic country. In the process, of course, consigned large amounts of what was decrepit and stultified and moribund in Britain, essentially over — and that included, for example, the great coal fields of the north, which were draining the public treasury and forcing people to go down into mines.

It was absurd, from my point of view. But people really hated her. (I just loved her.) And she became this sort of bête noire. Because she was such a formidable figure, reelected three times, transformed the country, a woman, a Tory — all these things just were too much for some people to even begin to absorb. I have a piece in the book called “Thatcher, Liberator.”

They didn’t even see her extraordinary pioneering work as a woman leader, as a woman who was a professional woman who earned a living as a chemist and a lawyer, and who took on the Tory party. I think it’s an amazing story, myself. I think she was more right than wrong about almost everything, with a few obvious errors.

I don’t get it either. My peers in England will still get so upset about her. She’s been dead. I don’t get it.

COWEN: What do you think were the main disadvantages women faced in politics, and are any of those reflected in views on Thatcher?

SULLIVAN: Yeah. Well, I remember —

COWEN: Is there less emotional space that women are allowed to inhabit, just like Barack Obama knew he could not get away with being very angry very often, if at all, right?

SULLIVAN: Right.

COWEN: What are those constraints for women?

SULLIVAN: You would think the constraint would be you can’t yell, you can’t harangue, you can’t be aggressive and debate without backlash — but she was all of the above. She did not make any concessions to her femininity in terms of being a politician. The House of Commons itself, just the format of the House of Commons is so gladiatorial, it’s so much a theater, that politics in Britain has to have this slightly parliamentary, theatrical element to it.

I think politics has often had that kind of dramatic theatrical element to it, and that doesn’t seem to come as naturally to many women as it does to many men. And that is a problem for women’s access, even though they’ve made huge strides in Britain — already had two female prime ministers, for example — as opposed to the United States.

One thing that’s interesting, also: that Thatcher and, for example, Theresa May (and also Angela Merkel) — they were not understood within their own politics in the way that Hillary Clinton was understood within American politics. It’s just not that big a gendered gap. In fact, if you look at the voting numbers, you find that there is almost no gender gap between Labour and the Tories in Britain. It’s a very American phenomenon, this idea that a woman in politics is somehow the symbol of feminism and of breaking the glass ceiling and all of that. It’s just not taken as seriously in Europe as it is here.

On things under- and overrated

COWEN: Now, in the middle of all these conversations, we have a segment: “Overrated vs. Underrated.” I toss out a name, a place, an idea; you tell me if you think it’s overrated or underrated. When you’re ready?

SULLIVAN: Awesome. Yes, I’m ready. Go ahead.

COWEN: Elton John: overrated or underrated?

SULLIVAN: Just trying to figure it out. I think he’s rated pretty accurately, to be honest. I don’t think either. I mean, I think he’s a great genius. Without Bernie Taupin — OK, overrated without Bernie. Those lyrics are hard to beat.

COWEN: David Bowie: overrated or underrated?

SULLIVAN: Underrated, underrated.

COWEN: Why?

SULLIVAN: He was so smart. This man had such a vast erudition, insight. I mean, I don’t know whether you’ve seen that remark he made about the future of the internet. He was smarter about what was coming than almost anybody else. And the creativity of this guy. I mean, we have all this lame, nonbinary bullsh*t today, and he was in the ’70s actually exploding differences to men and women, being androgynous while being incredibly heterosexual. Just — just a fantastic individual. That’s why my dog is called Bowie. After him.

COWEN: Oh, great.

Charles Dickens.

SULLIVAN: I think rated correctly.

COWEN: What’s your favorite book by him?

SULLIVAN: By him? I think David Copperfield.

COWEN: The State of Utah: over- or underrated?

SULLIVAN: Underrated.

COWEN: Why?

SULLIVAN: Have you looked at the statistics? They’re incredible. [laughs] I think here’s a tribute to Mormonism: One of the great crises affecting America is this atomization, this lack of meaning, this lack of community. Then the Mormons have shown you don’t have to do that.

Now, I’ve also experienced the other side of that, because I had a lot of time there with many of the gay groups there, back in the ’90s. But again, in Utah they came to this wonderful Utah compromise between the Mormon church and the gay rights groups, which really allowed both of them space to breathe. Romney — I would dearly love that guy to be president, if we had a Republican.

Definitely, underrated.

COWEN: Theresa May: over- or underrated?

SULLIVAN: Underrated, because she was given a basically impossible task. She did as well, I think, as anybody could have, and it was necessary, I think, to actually spell out how Brexit would take place, which required a certain process of the country and the country’s elites running out of excuses to do it. And that was always going to take time, and she took the brunt of it.

I think she’s underrated the way that John Major, for example, is underrated as prime minister.

COWEN: The musical group Queen.

SULLIVAN: Underrated. How could you overrate Queen? It’s amazing. Freddie Mercury, as a figure, is another gay icon to me, who I think is — a lot of people saw that movie, Bohemian Rhapsody, but the songs that man wrote: we still sing them. We still hear them. They’re still part of our culture. Again, another incredibly original gay man. For a gay man to conquer rock and roll with no real posturing about it.

A lot of the stuff that we celebrate today, the first person to — people did it before under much harder circumstances and didn’t sit around asking to get a gold medal for it. He came from a very conservative background and yet he lived his life. All those football fans chanting songs realize they’re chanting this super-gay man, I find fantastic. I love that mishmash.

I hate the separatism. I love when gay stuff is embraced by straight people and vice versa. I love the possibility of cultural mixture and energy that comes from that.

COWEN: What’s your favorite movie?

SULLIVAN: Airplane!

COWEN: Why?

SULLIVAN: I watch it every year because it’s just so funny and stupid — and, as a tonic, if you’re weighed down by the world, especially if you’re weighed down by wokeness or the incredibly censorious attitude that we have, it’s just so great to sit down and watch that every now and again and see what they got away with. And just the sight gags. I’m a big fan of sight gags and of slapstick, and so Airplane! —

I mean, I’m not saying it’s the greatest movie of all time or anything. I’m just saying when I think of movies I’m particularly fond of —

The other one I would say that comes to mind, if I’m being totally serious, is this movie called Into Great Silence, which is a Philip Gröning documentary on the monastery of Chartreuse, the silent order, which has never accepted any outsider its entire history since the Middle Ages.

He gets in and just films their life: their chanting, their work, the way they garden, the way they pray. This lasts for three hours and there are no words in it until the last 20 minutes, and you are riveted throughout. As an expression of spirituality, it’s an extraordinary film.

COWEN: Who’s the most interesting and underrated feminist thinker?

SULLIVAN: I still like Germaine Greer, to be honest with you. I just like her candor, her rigor, her energy, and her balls — if I’m allowed to say that. I’m not really allowed to — I guess you can now. [laughs] We can talk about a lady’s balls now the way we couldn’t before.

I’m a big fan of hers, still a fan of hers. She did some tough stuff, and she’s now actually also taking some tough stances, which I appreciate and approve of.

COWEN: Now, you often have described yourself as an Oakeshottian, right? Michael Oakeshott. How would you approach political issues where it seems you have to choose something ideological and there’s not an obvious way to do experimentation? Take, say, the Mexican-American war from the 1840s. How do you think about that? Are you glad it happened? Was it a big mistake? Is the Oakeshottian framework adequate to handle that?

SULLIVAN: I don’t know enough about the Mexican-American war, I’m afraid.

COWEN: You know we took the land and didn’t give it back. You know it didn’t belong to us, and you know it was a lot of land. I’m not sure you need to know the details of —

SULLIVAN: No, but — OK. I think as itself, would not fit an Oakeshottian understanding of what politics should do. Seizing land is not what Oakeshott’s conservatism will be about, but Oakeshott’s conservatism is very European and not as easily applicable to the United States in its formative periods. Sometimes it does seem to me that taking a bold ideological position on a public issue in which it is not so easy to simply compromise or cut into or finesse is necessary.

What Oakeshott would say is, “The key thing is, is such an act of radicalism actually a form of balancing?” For example, you could make an argument that Thatcher, for example, came in with a very radical, ideological agenda of shrinking the state, lowering taxes, cutting spending, etc., which was ideological. Why does a Tory support it? Because the country had so gravitated towards a nadir of socialism that, in fact, that kind of ideology was necessary pragmatically to return Britain to its center, as it were.

So sometimes radicalism is a necessary part of moderation. How do you determine which incident or which moment in history or which decision is that decision? The conservative in Oakeshott would say you can’t, that that is where you cede to what we might call prudence, prudential judgment, which is where we rely upon the individual politician, the individual statesperson to have the judgment necessary to make the right call.

It will not be prescribed in advance; it will be hard to determine retroactively; but in the moment, a person able to make those kinds of prudential, practical decisions is the person that we should follow. The goal is to keep the society on an even keel, not to disrupt it too much, even though sometimes it takes radicalism to keep it on an even keel.

COWEN: At the state level, do we have Oakeshottian legislators today in America?

SULLIVAN: Well, fewer and fewer, because of the way in which the gerrymandering particularly has made it more important for incumbents to worry about primary opponents than their general election opponents. But I do think, and I’ll echo David Brooks here, that there is more of it than you might imagine — that there are practical things that need to be done, things that need to be rearranged as the society changes and moves, and there are people in politics capable of doing that, who have done that.

And certainly at a state level that’s increasingly the case. There are just complicated, difficult things that require administrative skill and political judgment. I think that kind of political judgment, which is not to be too driven by ideology in all things, which will allow the possibility of a prudential, pragmatic adjustment, is what Oakeshottian politics is at some point about.

COWEN: Do you think the American Southeast will walk away from the pandemic as the least traumatized or most traumatized part of the country?

SULLIVAN: It could be the most. I think the experience of having had an opportunity to avoid a catastrophe and then walking right into it is potentially much more emotionally and psychologically traumatizing than just having something happen to you that you had no warning for, and that you couldn’t have prepared for but which knocked you out — the way New Yorkers I think were traumatized by 9/11 or indeed the first wave of COVID.

COWEN: If I stay in Miami or Nashville, it seems to have returned to normal much more quickly than in San Francisco, and people have a more casual attitude about it that seems to be bad from the point of view of casualties, but there’s lower unemployment, more rapid bounce-back. Won’t they walk away —

SULLIVAN: I see that too. My worry is that the Delta variant is also going to mean a lot of death in the next month or two, much more death than might otherwise be the case. We’ll have to wait and see how that affects this understanding. In general, as you know, I’m in favor of getting on with life and getting back to normal as quickly as possible. I say that as someone who is particularly vulnerable to COVID, but I’ve looked at the risks, got my vaccination, and I’m going to live my life with some reasonable precautions.

I kind of appreciate where they’re coming from, but I — seriously, Tyler, I don’t understand why you wouldn’t take a prudential measure to save your own life when it’s available to you for free. Maybe I’m so used to having my body medicalized that having another needle stuck in me feels so routine at this point that I can’t understand the idea of people who really aren’t part of a medical system having to subject themselves to it for the first time on the basis of a potential illness.

We’ll see, won’t we? My hope is, it might be the case that Delta’s going to blow itself out quite quickly. It seems to be happening in Britain right now. They may not, but I do think there’s a chance that they’re going to suffer terribly, and suffer on top of that the sense that they could have avoided it, which makes you doubly traumatized.

COWEN: Now, you’ve supported both Obama and President Biden on the grounds that they would help us get past the culture war. It seems in a lot of ways, culture war has gotten worse. What’s your view now? Is it, “It would have been even worse yet without those figures”? Or maybe, “Obama made it worse in ways I hadn’t seen at the time”? Give us your current model.

SULLIVAN: You realize, I think, that the individual president can’t unravel these forces that have been propelling us now since the 1960s, really. That was the thesis of the Obama support, was that he could get us past — that he’s the first non-boomer, or post-boomer, to really be able to slice through pragmatically this deep Right-Left, somewhere-nowhere, heartland-coast divide.

With Obama, again, I look at it and I’m like, I’ve really tried in my conscience to see, Did he really inflame racial relations or the culture war in ways? I honestly don’t think he did. I think he tried quite hard not to, which is in stark contrast, of course, to Trump. I think Biden is more at fault than Obama, even though Obama was much more ferociously opposed, because of his complete embrace of critical race theory and the diversity-equity inclusion agenda across the government and elsewhere, whereas Obama was really very hostile to those things and resisted those things.

But I’m sobered up by the fact that I never fully understood how Obama was as unpopular as he was in many parts of the country. I honestly can see some aspects of his personality could rub people the wrong way, but his core decency always seemed to me quite self-evident.

I have to conceive simply that Americans — I always believed Americans would be willing to elect a Black president. I underestimated how willing they would be to be governed by one. Some deep racial stuff I had underestimated came to the surface.

On wokeism

COWEN: If we look at the world as a whole and recognize there’s some globalized element to culture and just to ask the simple question, “The world as a whole, should it be more woke or less woke?” Which would you prefer?

SULLIVAN: As a whole? Well, no one —

COWEN: There’s Pakistan, right? There’s how gay people are treated —

SULLIVAN: Right, right, right. Well, no, but woke does not mean socially advanced or progressive. It doesn’t. It has a very clear view that the West is essentially — has been a construction of oppression rather than liberation.

COWEN: But it’s a number of things. Take, like, the 200 most woke people in San Francisco and give them more influence, like their views have more influence all around the world. Does that make for a better world or a worse world? Doesn’t it make for a better world?

SULLIVAN: I think it probably does, if you’re considering Saudi Arabia [laughs] or if you’re thinking about Central Africa.

COWEN: So you belong to the faction of woke?

SULLIVAN: [laughs] Tyler. I belong definitely to the faction of people who want to see minorities and people who have been previously marginalized in society being given the full opportunities to become absolutely fine, full, contributing members to our society. You can do that through a liberal system. In fact, I think the liberal system is the best way to do that, the least divisive and the more psychologically productive.

In that, if I could find a way to make the world more respectful of those ideas, I would, but wokeness is not about that. It is about the notion that the world is defined by oppression — is not just defined by oppression, but defined by white oppression. I think if you took the lessons of the woke in terms of the inherent conflict between white and nonwhite — the nonwhite world — we’re talking about a major global war. A major, non-zero-sum global conflict, which — it would be a zero-sum conflict in the United States if they really had their druthers.

And so no, I’m not woke, not globally, but I do believe —

COWEN: That it has a positive marginal product? It may not be your preferred ideology —

SULLIVAN: Maybe — maybe, maybe it has a marginally social product.

But I do prefer societies where women have equality and choice in their lives. I do believe in societies where gay people aren’t murdered and persecuted, where antisemitism isn’t — all those things. Of course, I’m a liberal: I believe those things. I just think the means by which you get there matters.

COWEN: Why has wokeness done so well, at least along our coasts, in passing a kind of market test in many of our most productive companies? Now, some of it’s the government — governmental support. But clearly it goes far beyond that, right? How has that happened? What’s gone wrong in the market?

SULLIVAN: Well, it’s less the market than the elite market, because it’s the elites that have made these decisions. This isn’t coming from a wellspring of American suburbanites demanding that they go through struggle sessions on their complicity in white supremacy. That hasn’t bubbled up from below.

Here’s why, I think. Because the elites kind of have a Martin Luther King Jr. envy. Every generation wants to have that moral quality, that sense that they are shifting the arc of history in a better way, even though we’ve generally done about as much as we possibly can to do that in terms of — within the possibilities of — a liberal system. There’s that. The need to feel worthy and the need to feel that you’re doing things.

It’s also much more conducive to human nature to see people in terms of groups rather than individuals. It’s just much more comfortable for people to do that. We are essentially tribal. What wokeness appeals to, in the way that the far right also appeals — it appeals to tribalism. And tribalism in its cruder sense of being able to identify people instantly as a member of your tribe or another tribe.

That is how humans have always lived. So of course it’s likely to be more successful when you combine it with the sense of moral righteousness as well: to tell people you can be tribalists and moral at the same time is an incredibly attractive way of life. To be able to see a white male and know instantly that that person is part of the problem before you even talk to them is hugely rewarding for a human psyche. Always has been, always will be.

Liberalism, the achievement of seeing the individual independently of his or her group, is hard; it’s counterintuitive. It’s always on the defensive in many ways. Whether it’s a tribal right-wing racism or whether it’s a tribal left-wing neo-racism, they come more naturally to humans than the liberal discipline.

COWEN: Last question: You said toward the beginning you wanted to travel more. Let’s say you had two free weeks, all expenses paid, no responsibilities, no COVID restrictions — where would you go, and why?

SULLIVAN: I would go to Rome, which I’ve never fully really discovered, I never really spent that much time in. I would probably go to Rio. I don’t understand South America very well, and there’s something about that city that really compels me.

I would go to Ireland because it’s also an island where most of my family comes from. I’ve never really spent time in the west of Ireland where my ancestors came. My brother went around there recently and he said, “You know, it’s funny. I went to this little town in Cork and they all look like us.” [chuckles] There was a sense of, I’d like to get in touch with my ancestral roots by glowering at the grim Atlantic Ocean and the steady rain and the bleak sky and get in touch with their grit and their resilience.

That’s where I’d like to go, those places. How’s that?

COWEN: Andrew Sullivan, thank you very much.

And again, Andrew’s new book, the definitive statement of Andrew Sullivan — it is called Out on a Limb: Selected Writing, 1989–2021.

SULLIVAN: Tyler, you lived up to your reputation. Those were fantastic questions delivered with merciless speed and energy. I’m so grateful. I’m afraid I didn’t do as well as I hoped to, but nonetheless, thank you for having me.

COWEN: Oh, great dialogue. Thank you.

Thumbnail photo credit: Chad Norman