EO

I wanted to start with a quote from the piece you wrote for The New Yorker on Lauren Berlant in 2019. You say, “The persistence of the American Dream, Berlant suggests, amounts to a ‘cruel optimism,’ a condition ‘when something you desire is actually an obstacle to your own flourishing.’” You continue, “These feelings, Berlant says, are the ‘body’s response to the world, something you’re always catching up to’” and finally, “Cruel Optimism” was dense and academic, but it proved enormously influential. Its timing was serendipitous. The book was published at a moment when Barack Obama could still credibly draw upon “the audacity of hope,” and, with a second term in sight, people wondered if he would finally unleash the progressive will that many believed lingered deep inside him. Those who opposed him continued to work themselves into a radical frenzy, as the Republican mainstream reoriented itself around the Tea Party. Berlant tuned in to a wider sense of disaffection—the feeling among average voters that neither of these visions for change was really about them, or for them. According to Berlant, these suspicions manifested themselves in mundane ways: hoarding things or overeating might be attempts to overcome feelings of personal powerlessness. And her affective framework was a means of understanding larger manifestations of these suspicions, too: the Occupy movement, which began in September, 2011, could be seen as a response to the cruel optimism of capitalism, the pent-up outrage of citizens realizing that they’d been chasing nothing more than a dream.”

I read that because as I was reading Stay True, I felt criticality is the driver in the vehicle of optimism in your memoir. You often talk about friendship and loneliness and self-involvement, but I feel like all those things are required for any kind of optimism. They’re productive. I was thinking about how productive disappointment is. I was also thinking about how the condition of suffering is connected to the production of and impact of different mediums of art. Do you think you could’ve written this essay today?

HH

I forget that I wrote the Berlant piece actually. [Laughs.] I think that there’s actually a dumb optimism in a lot of what I do. I think with criticism and writing for The New Yorker, or just writing as a journalist, it’s a great excuse to binge all this different information. So with that piece, I spent a month reading or rereading all of their work that I could get my hands on, and it’s something that I would’ve wanted to do anyways, but we don’t make time to do things like that. Nobody does, unless you’re in graduate school, and that’s not an ideal form of learning. You rarely have a chance to just immerse yourself in someone’s thought. So that piece was me trying to understand Lauren’s work for myself, and I think that a hardcore scholar of affect theory and Lauren Berlant might have bristled at my direct application of the idea of ‘cruel optimism’ to, I don’t know, Obama’s America. But that’s just how my mind works, where I don’t necessarily think I’m capable of generating ideas that are that deep, but I like connecting people with other people’s ideas or art. As a critic, I always view myself as the person telling a story about a piece of artwork that hopefully will move people the way that work of art or that set of ideas moved me.

So that’s sort of separate. I think the idea of affect theory, cruel optimism, it was very clarifying to have those ideas, to see them in the world, and to see the world in you as a result of those ideas. I think personally, deep down, I hold on to a very dumb optimism, which might be naive, but it’s sort of how I have to see the world, which is, I agree that everything is shit, but I need to hold on to pockets of things that are hopeful. Some of them I view critically. Some of them I protect from criticality too. But I think criticism, engaging with art, going to see art, reading, it’s all a way of getting outside of ourselves, which is a goal that many of us have, but it’s hard to actually embody.

EO

Can you define what ‘dumb optimism’ is?

HH

You know, I've never thought about it until right now. When you’re describing things like loneliness or suffering, it’s hard to separate out an actual belief versus rationalization sometimes. I think we do have this desire sometimes to turn anything into a productive spur. It’s kind of like how in the business world, people are like, “You got to fail in order to succeed,” which I kind of agree with. [Laughs.] But I think that my perspective on what it means to fail is very different from what a business school professor thinks.

EO

What do you mean?

HH

My first book was on this Chinese proletarian writer H.T. Tsiang. I feel like he sought failure. He was so rejected by the system that he courted a kind of radical failure. I think Jack Halberstam writes about this in The Queer Art of Failure, that there are ways to fail so radically that it casts the whole system into doubt. It’s not like, "Oh, I started the startup and it didn’t work, and now I have to go back to the drawing board." I don’t know if I have the bravery to radically fail, but…

EO

What does it mean to radically fail?

HH

You know the rapper Lil B, and how he has over 3,000 songs in his discography, he will never succeed by traditional metrics. It’s literally impossible. But there’s something about that approach that aims to fail by traditional metrics. I think I’m copying what Jack Halberstam wrote in The Queer Art of Failure, where there’s certain ways in which you can produce things that deny the possibility of the market altogether or aspire to deny entry into capitalism, and it fails by those metrics, but it might be what the person actually wants to do. It’s actually much harder to do that now. It’s kind of impossible to do that because of the internet.

EO

It’s a fallacy.

HH

Right. So this guy thought, he wrote books back in the 1930s when a book could only mean one thing basically, and nobody wanted to publish them. So he would publish them in bizarre ways, as a sort of negative blur. He was critiquing what it meant for a book to exist. And I think it’s much harder to do that nowadays, the way society is constituted, the way capitalism frames everything we do or think.

EO

Yeah. Why do you think that is?

HH

I think it’s just so pervasive, and I think whatever casual friction once existed, it’s much harder to find now. But that sort of goes back to the whole thing of there’s something productive about disappointment or loneliness or sadness. But then sometimes I’m like, is it allowing ourselves to be co-opted by the grindset mindset to think that even loneliness should be productive? You know what I mean?

EO

[Laughs.] Of course I do.

HH

I actually believe it, but then I’m also like, am I just too in the tank now that I think, “Oh, I could turn these negative feelings into something useful or something else?” But I do believe in what you just said for myself, I do think that there’s something meaningful about sitting with negative emotions or ambivalence. I think that as I grow older, I’m trying to protect them from thinking like, I should write this or publish this or do something with this. Does that make sense?

EO

When I say productive disappointment, I don’t mean it as a framework. I mean it as a description of a state of existence. Namely just being present with how you're feeling.

HH

I get what you mean. But I think that on a piece of paper or on a screen, if someone reads that, you could see that as the next Michael Lewis book or something. [Laughs.]

EO

That’s why I’m breaking it down, because it’s a double entendre in a structural sense. It's possible to be sad and still maintain your ambitions and have your desires rooted in something meaningful. I was thinking when I read your writing, because I’ve read your writing for years, and you do write about Derrida, you write about Lauren Berlant, and you write more generally about Asian culture. But I’m curious what it is that you think that you do? You’re not a great writer because you’re Asian American. That’s what you choose to use as a vehicle to paint the world, but your subjectivity isn’t your talent.

HH

That’s kind of you to say. You mean, why do I write? What do I write about? That’s a huge question that I think about a lot actually, because I think I’m at an age where I don’t want to just keep doing things just to do them. An easy thing to do would be just to continue doing, and it’s not like I’m going to radically change and become a painter or something. [Laughs.] When I try and find coherence in my career, I’m just really interested in how people imagine the world and its limitations. I remember when I got to graduate school, I had read very little that wasn’t published in my lifetime. I was definitely one of these people who just was interested in the present. The only things I read were histories of the Black Panthers and the civil rights movement and the Asian American movement. I did not read fiction. I had never read The Great Gatsby until I got to grad school. I just didn’t really care about all these things. And going to Berkeley, that was perfectly fine. But then once I got to Harvard and I realized how wigged out the modernists were, or how interesting the period right after World War I was, or even just what it meant for Melville to idolize Hawthorne and really want to impress this one person for a stretch of his career, it not just deepened my sense of history, but then I also felt, “Wow, it’s wild that was this person’s ambition or this is how this person imagined the world.” When it comes to criticism, when I was writing about rap music at the same time that I was taking these classes on the American Renaissance. I think the thing I was always interested in was, What is the circumference of your imagination? And what goes into the size of your imagination?

EO

How do you feed your imagination?

HH

Yeah, exactly. Why do you think that’s impossible? And why do you think this is possible? And part of it actually goes back to the capitalism question, where you read stuff written in the 1930s and these were all socialists by today’s standards, you know what I mean? Just how casually these people who are now canonical had radical visions of what society could be. They weren’t completely enlightened in ways we’re enlightened. But that just means that a future generation will look at us and see our blind spots too. That’s why I’m interested in anything and everything. Why do you think that’s what you should do and what does it say about the world as it seems to exist in your time that that’s what you did?

EO

It’s being a historian. [Laughs.]

HH

As a critic, I’m way more interested in that question of the history of imagination more so than telling you whether something’s good or bad. I’ve never felt confident in saying that’s good and that’s bad. That’s never been my strong suit or inclination as a critic.

EO

I’m definitely of the same mind. What I, Emmanuel the person, thinks doesn’t matter—it’s my job to connect the dots. Then how would you describe when you’re drawn to something and then how you go about communicating the meaning of that thing?

HH

I’m more drawn to what the world means and trying to locate a piece of art that can allow me to think about that larger question. That’s actually why I write less music criticism now because I don’t have a strong sense of faith in my own read of how music and the culture interact. A lot of people could be given a piece of music and evaluate it purely on its own terms, free of context, but I’m a context person. I’m interested in the context and I just want to see how the context trickles down into the artwork.

EO

I’m asking this question selfishly because increasingly I’m seeing people engage with art in such a flippant way, where the metric is either good or bad. Or for Beyonce’s new Cowboy Carter album, because she’s become this kind of cultural behemoth since 2018, I was speaking to this person the other day about the craft and rigor of the album and they were like, “there are definitely some skips.” [Laughs.] I’m a process-oriented thinker and appreciate taking my time dissecting and living with things. And I feel “some skips” has become a new shorthand for when people don’t really care to take time to learn about things they don’t understand. It isn’t productive to feel the need to be an authority on everything happening all the time at once. [Laughs.] That’s not even the right framework to approach any sort of art. Because if you don’t understand the context, you don’t actually know what makes it good or bad, right?

HH

Right, there’s still a critical response, but I’m less interested in interrogating my own critical response than I am the context. But that doesn’t mean context can make me like something that I don’t like. But I’ve never really thought too much about why I like things I like.

EO

But as a person that really rigorously consumes, is drawn to ephemera, reads a lot, archives, collects, you have a really serious relationship to time.

HH

I do, but I don’t think being into old stuff necessarily makes you a good critic or even a critic at all. We’re also talking in April 2024. I haven’t really written criticism in quite a while. I work a lot with initiatives around criticism. And I’m really interested in criticism as an idea and the health of criticism, but I don’t feel as connected to how criticism circulates now.

EO

Why don’t you?

HH

For example, I kind of stopped writing about music full-time a couple years ago. I actually know the moment. There’s these two Pink Pantheress songs “Break If Off” and "Pain” that I thought were really good and I liked her vibe because it was this sort of like pop take on ’90s jungle music. Really fun to listen to, but you know the reason she was so popular was because she went viral on TikTok. I’m the type of person who just accesses a curated version of TikTok on certain people’s Instagram accounts, so I was sort of like, “I don’t understand why most people like this.” I know I like it, but I also know that why I like it is separate from why it became popular. I also just felt like there are certain forms of criticism that benefit more from younger, even more diverse, whatever that means, voices. And I didn’t want to take up space, being not as plugged in as I once was. We’re just going to go on some tangents now okay? [Laughs.]

EO

No, I’m ready.

HH

You know Theo Parrish?

EO

No.

HH

He’s from Detroit by way of Chicago. He’s a DJ and producer. He does these like eight hour sets. He’s just been someone I’ve admired for like 20 years. And I just bought like a whole stack of his mixes throughout the last 20 years and there’s like a real imperfection to the way he DJs and now it seems kind of cliche because I think that many people living now have heard old people talk about how much better vinyl is, and that’s a tiresome discourse, but he plays a lot of vinyl still. I like it when my records skip because perfection is boring and that just tells you how long I’ve had this.

He did this interview in Blank Forms, it was like 200 pages long, and he has all these things to say about how if you’re dancing to one of his sets and you hear the record skip you’re sort of connected in this moment of human imperfection with him. That’s stuff that I implicitly accepted in the ’90s when I would go hear like a scratch DJ or someone and you’re like, that person is clearly physically exerting themselves. But there’s something about what I get out of listening to Theo’s sets that isn’t a question of me being able to point out that this is the moment that makes him a good DJ, like that transition or that track selection. It’s more about communing and that recognition of humanity. So lately I’ve just been less interested in interrogating why I think things are good or bad but just understanding the context, understanding the context of how, why I might gravitate towards something now that I didn’t like before.

EO

Two months ago I started listening to classical music, something that I’ve actively avoided for my entire life, and now I’m like I don’t know if this is good but it’s sort of like thrown me off a little bit listening to music that I have no history with and no way of contextualizing at all, but it’s also kind of nice to not feel the compulsion to do that. The elephant in the room is the Pulitzer. [Laughs.] How does that psychologically change how you engage with writing? I wanted to bring up Louis Menand, who won a Pulitzer in 2001, and he was your advisor at Harvard, because what are the odds? Reflecting upon that time when you were back at Harvard, why were you drawn to him? How do you feel having received this prize? How has it changed you?

HH

First of all, it was fucking crazy, a shock, and unexpected.

EO

What happened? How did it happen? Where were you when it happened?

HH

I didn’t put myself up for it. I didn’t know the category existed, either. I won for ‘autobiography or memoir.’ It was the first year that that was offered. It obviously changes things in all the obvious ways, where it’s something that my parents could recognize. When I told my parents, my mom started screaming, and I’m like, “You know what that is?” And she’s like, “We’ve been here since the ’70s. Of course we know what that is.”

When my friends and I all started writing for magazines, we would think, “Which magazine is the magazine that you could write for that anyone you would meet at an airport would know?” It’s just sort of a wild thing to have gotten. I don’t even think it’s an achievement. It’s really just luck. Because I’ve been on judging panels and it’s a wild fortune to have been able to do it.

But I think it’s been sort of strange because it’s not like I was a deeply autobiographical writer before. I think everything I write, everything anyone writes, is autobiographical because it’s filtered through your own perspective. Over the past 10 years, even at The New Yorker, you can insert the first person into a piece of criticism just to position yourself and to make that position clear. And there’s political value to that. Makes the writing easier. But I’ve never been this confessional writer and so it’s been sort of strange.

EO

And it was weird. I know your writing intimately because I’ve read you for so long and reading your book was so crazy disorienting.

HH

Right, because it was a very different register.

EO

It’s hard to hear you talk about self-involvement. The pursuit of writing is that. There was this quote that you have about Derrida, a favorite of mine, but you say, “Stories about love offer models for how you might commit your life to another person. Stories about friendship are usually about how you might commit to life itself.” Then you say, “By the time that he delivered his lectures on friendship, Derrida had become entranced with a line attributed to Aristotle, o philoi, oudeis philos. The line is often translated as, "O my friends, there is no friend"—a strange sentiment, at once an acknowledgment and a negation. Some speculate that Aristotle was expressing something simpler, closer to ‘He who has many friends, has no friends.’ But Derrida was drawn to the seeming contradiction in the version he favored. He thought that figuring out what Aristotle meant could point us toward a future of new alliances and possibilities.”

I agree with the latter more so with the former. It’s like, he who has many friends has no friends. But I think that that really registers in your writing. You’re friends with all these people that you’ve written about, or you befriended all of these people that you’ve written about, be it Baudrillard, Derrida, Berlant.

HH

I think that there’s a connection there where I did want to write about my actual friends in this book the way I write about figures. I like the idea that in my book, I quote my dad, Ken, and then Aristotle. That they’re all on equal footing. You just read a passage from the Derrida New Yorker piece. I didn’t come up with any of those insights about Derrida’s interpretation of Aristotle, I just finessed the language after just reading tons and tons of interpretations of Derrida.

Going back to the question you asked before about graduate school, that’s what attracted me to the people I worked with in graduate school. When I was in my PhD program, I recognized that I wasn’t the one who was going to come up with the heavy idea that was going to fuck up our seminar professor. I wasn’t the one who was going to drop that. But I wanted to have the conversation. I wanted to be able to take this idea somewhere else. Like, we’re talking about this here, and I’m kind of barely keeping afloat, but this is a useful idea. Let’s talk about it in this other context, in a way that’s still semi-rigorous, but makes it useful, because ideas can be useful. In grad school, I tried to extract as much as I could from my professors, my readings, and whatnot, but I became really drawn to not presentation but circulation. How ideas circulated and how you could make dense ideas accessible.

I remember in one class, Menand was explaining something for seven or eight minutes. And then he finishes and says, “There, now you understand deconstruction. Have a good weekend.” And I was like, I’ve always wanted to understand deconstruction and I’m a little bit closer now. It was the way he was able to tell this story about this idea. And I think that’s what I’ve always wanted to be able to do, and that’s why I was drawn to him as a graduate advisor because he was a master at storytelling.

Within academia, there’s still conservative attitudes toward that kind of intellectual work, which is more about connection or juxtaposition, or making ideas open to everyone, but that’s where I saw my potential contribution, if I could make any, because I could never come up with a theory. I was always interested in so many things at once that I was never going to disrupt any specific field.

EO

But what specifically about Menand were you drawn to aside from his form of storytelling and communicating ideas?

HH

It was that. It was just that he was such a good writer, and I wanted to understand how to write well.

EO

I wanted to bring up this interest in pragmatism. I read that you wrote about Menand’s book The Metaphysical Club in your thesis. I read a lot of work in grad school on Charles Sanders Pierce. Pragmatism made me think about Marshall McLuhan. I remember watching this YouTube video of him in the ’70s where he was saying that reading is an exercise of rapid guessing. I think that folds into this idea of pragmatism. Weren’t you at Harvard when Zuckerberg was there?

HH

Yeah, but I was in grad school, so different from being an undergrad, especially at a place like Harvard, where I would be the TA for students who I was pretty sure would one day be my bosses and editors. I don’t know. To be honest, I didn’t make the best use of graduate school, in the sense that I don’t feel like I retained a lot of information. I retained a lot of methods, but the things that I remember the most are not the things that my professors taught me, but more of the things they showed me, just how to treat people or how to explain things.

I took this class and Henry Louis Gates was one of the professors. And I have no real take on Skip Gates at all. This was just this random seminar where he would show up and riff. So, what I learned wasn’t pedagogical, but at the end of the semester, he invited us to his house. He had a bunch of Romare Beardens or something. He had an incredible art collection. And he said something like, “I just collected what I liked.” And now he has this incredible art collection, but he was like, “I was just a kid and I was meeting these artists, learning about this stuff, and I just collected what I liked and I didn’t know that it would one day be this foundation for African American art.” I don’t know why I thought that was so interesting. It was the sense of the education that was so canonical, but that you still had a sense of personal taste. So, I’m reading all this stuff that I never read before because I had, much like classical music for you, I dismissed out of hand, but then every now and then one of these professors tasked with making me read the canon would remind me that they had this ironic thing they liked, or this fascination with this one style. But it was that you could still take those ideas and do something else with them for yourself.

EO

That is how I felt at grad school. Like you're indoctrinated into this world, into this club, into this life. And then it’s like a form of acting. You encounter this language (pedagogy) and there are standards and appropriate modes of expression, appropriate models of communicating these ideas, but it’s a form of method. You purely learn method and what ideas are worth pursuing. What is it like for you being a professor yourself now?

HH

It’s pretty different. I’ve always been inspired more by my college professors than my grad school professors. It’s not professional. You’re like a sponge. I went to college in the mid-’90s, like ’95 to ’99, and so we didn’t really have the internet in quite the way we have it now, and college was where you went to be exposed to the rest of the world. I think, now, when you get to college, you already have access to the rest of the world, and it’s about, I don’t know, learning how to live with other people. So I wanted to become a college professor because I remember sitting in a lecture with 300 other people learning about, I don’t know, the Japanese internment or something, and then being so incensed that I’d never learned this before, and that one day, I would be on the stage giving these rousing talks. But now people don’t come to college for that experience because they already know about everything or they’ve heard about things or history just has a different status, and so it’s very different. I try to disrupt what you described as passing on the methods, like the method acting osmosis thing, because I want students to not think in terms of these pre-existing frameworks. Like, I want to know what they actually think about things. That’s a little harder to get at nowadays. It’s like the Beyoncé thing you said earlier about someone saying “there’s some skips on there.” Like, sure, but tell me what you’re skipping and why you’re skipping it and tell me what you’re not skipping and why you’re not skipping that. I always tell my students, and it’s probably the only consistent thing I’ve told students from 2007 to now is, one of the points of college is for you to be able to explain why you think something sucks, because we’ve all walked out of a movie and felt like that sucked or that was mid, but being able to actually explain why you think that is a pretty useful skill. So, that’s different from why I went to college, right? When I went to college I was like, I’m going to open my brain and pour all of Marx, Heidegger, and Freud into here because otherwise I will never have access to this stuff. Whereas now I think a lot of 20-year-old kids on Twitter understand these concepts more than I do, because they’ve had access to them in more digestible ways for a longer time than I did.

EO

But I think they’re missing that context of what actually positively reinforces knowledge production because it’s like the form of archiving, the importance of history.

You talk about What is History? You said, “The paperback copy of Edward Hallett Carr’s What is History?…He left the book at my apartment in case I ever deigned to actually read it. Carr published What is History? in 1961. He served as a diplomat for many years before pursuing a life in academia where he published a series of influential works on international relations. This history begins as a series of lectures he delivered at Cambridge. When we attempt to answer the question, ‘What is history?’ our answer consciously or unconsciously reflects our own position in time as well as the future we hope to see…” Then going back up, you say, ‘I read the description on the back, ‘This is all basic stuff, right?’ I said to him. I passed off something I once heard someone say about Hegel. “We know this already, right? History is a tale we tell, not a perfect account of reality.” I continued, “You just have to figure out whether you trust the storyteller.” I really feel like that is your pursuit of providing context as an exercise in getting a person to agree with you, which is what you started off doing almost 30 years ago, when you were writing and making these zines.

HH

Yeah. I probably wanted people to agree with me more then than I do now. Now I feel less fixed.

EO

As a result of what?

HH

Just being older, but I think a lot of writing and teaching is about making things seem inevitable and giving someone a set of contexts to steer them toward the conclusion you want to steer them toward. But there’s also something a little dastardly about it too, like when Menand ended the lecture saying, “Now you understand deconstruction.” Like, it’s because he told such an elegant story about something. When you’re teaching or when you’re writing, you’re setting up this scaffolding. That’s not the right metaphor. You’re guiding them down a path and you wanted to make it seem like this is the inevitable path, that this was just what was going to happen. But as I spent more time as a critic, more time writing, and grew more skeptical about some of my older takes, I’m more interested now in being on this inevitable path with someone, and then pointing out other things. And maybe we could figure them out together.

It’s a product of being older, but also wondering what the utility of being right is. I see less and less utility around that, for myself at least. One thing that was destabilizing as a critic was how, around the 2016 election, realizing that there was this fascistic right-wing approach to the movies of John Carpenter or the music of Depeche Mode. Just realizing that you could like these things that I like, but for radically different reasons. It wasn’t like The Passion of the Christ, which I haven’t seen, but it wasn’t like conservative art being appreciated for conservative ways. It was like, you’re just interpreting They Live in a completely different way than it was intended and how I appreciate it. [Laughs.]

EO

Hal Foster talks about the importance of “good entrances." Which is how your intellectual thinking or work initially reaches the public and its reception. That’s kind of what makes or breaks a career. We have one opportunity to land the proverbial plane, right? That’s what he and I spoke about when I interviewed him about publishing his first book The Anti-Aesthetic: Essays on Postmodern Culture in 1983. Though it’s different now, where we first publish a piece and it goes viral, specifically around the 2013-17 period, or we publish a book and it becomes a cultural phenomenon. What I really kind of understood while I was in college at The New School is that there are different openings in culture. Life and culture is like an ocean. There are different tiers and different types of waves. It’s like riding the surf. I was riding the surf and became a photographer. That was my introduction into this world and then pivoted. Every medium has its moment in time when it is received as an art and has openings—slots that need to be filled. I think that you were really a part of this more contemporary movement, where criticism was an art. Criticism isn’t the same as it once was.

HH

Yeah, I think that’s probably true.

EO

With Roberta Smith retiring, I feel like that was a retirement of criticism…

HH

Yeah, I get what you’re saying. That’s why the right-wing thing kind of fucked me up because I was like, it’s pointless for me to say, “Depeche Mode is good” if the alternative isn’t “Depeche Mode is bad,” it’s “Depeche Mode is, like, fascist anthems.” [Laughs.] You know what I mean? I felt like as a critic, they were just practicing a fucking weird form of criticism. Like, they’re taking the same thing and telling a radically different story about it.

EO

Yes, using the method of criticism as a vehicle.

HH

I think it’s wrong what they’re doing. It sort of made me rethink what I was doing. Like, I think what I’m doing is correct and actually in the spirit of the music, but I was like, wow, it’s wild that these totally sociopathic forms of criticism persist and are actually thriving in ways that are totally different from what I do. [Laughs.] It’s not like I stepped back because I thought there’s no room for me against that, but I became more interested in, like, the larger political ‘What does this mean?’ And what does this mean to the history of criticism? When criticism was, like, A.O. Scott ripping The Avengers and getting blowback from Samuel L. Jackson, that’s a different moment than now because I think that there’s fewer people who have the autonomy of being full-time critics.

EO

And being protected.

HH

If that’s your only job, you have a degree of autonomy that a freelancer doesn’t. I remember when I was a freelancer in the 2000s, you’d be reviewing a rap record, but also writing bios.

EO

Or copy editing. [Laughs.]

HH

And so it’s not like you’re ever being intimidated in that process, but you are then implicated in the system. You’re more sympathetic to what they’re doing, which maybe that’s not a bad thing, but the days of Roberta Smith or people who are only spending all of their time doing criticism...

EO

Or doing one thing.

HH

It’s really different. I think the idea of not just that generation, but also the discipline-specific, genre-specific critic, it’s also a dying art because I think now there’s so much more glory to being a generalist.

EO

We lived in a specialist world until very recently. I moved to New York in 2014 and started college. You had to specialize in art history if you wanted to work in the art world. You had to specialize in English literature, comparative literature if you wanted to be taken seriously as a writer. There were these shorthands for personality types. We now live in a generalist world, but ironically I think institutions and specificity, not specificity of thought necessarily, but specificity of mission is more important than ever. There’s a difference between being decentralized and being a generalist. I think we need to end decentralization and welcome the mechanics of being a generalist and having multiple interests.

HH

I agree with that. It’s possible that a turn towards generalism just means very surface understandings of all of the different things, right? Like I find the art world so strange. I like going to the museum, going to galleries and whatnot, and I could look at a piece of art and have an opinion about it, but the rules that govern art or standup comedy, or literary fiction or popular music, they’re all different in these minor ways that I think we still have to hold on to. There’s a lot of things that happen in all these different industries that look very parallel, but they aren’t. It’s easy to recognize and easy to see the exploitation across these different worlds, but where they’re happening and why they’re happening might be a little different. Does that make sense?

EO

Yes, I was thinking about fashion people talking about music and their “the skip” is “the look was mid” and it’s the same structure. [Laughs.] It’s its own architecture. Fashion is its own architecture, art is its own architecture, music criticism has its own.

HH

And I think that needs to be acknowledged. But, for example, I think if we were to treat comedy like we treat literature, then there’d be no comedy anymore. Comedy is like the edgelord art form of all of these different things I’ve named.

EO

Or comedy is like the sum of all of these things’ parts. It’s a stage for all of the culture to be scrutinized.

HH

Here’s an example. Like the A&R of an album, the editor of a novel, and the curator of a biennial, they’re not all the same. Even though they’re all gatekeepers in some sense, we can’t necessarily treat them as the same. Even though we might look at a painting, a piece of music, and a book, as in conversation with one another. The larger institution or apparatus that produces these different artworks that, as a generalist, we might want to put in a conversation, they’re striving for different things at an institutional level. Sometimes, it’s easy to lose sight of that.

EO

When you say that they’re all not the same, do you think people are trying to make them the same?

HH

There’s no specific thing that I’m thinking of. The mode of consumption is so uniform.

EO

It’s like you’re passing through a book or music criticism.

HH

Because as humans, we recognize patterns, so it’s like if this image circulates, or this stereotype circulates across these three different art forms, then it says something about the cultural moment. But you also just have to acknowledge that different forms of cultural expression or different forms of art are compromised in very specific ways.

EO

Back to this PinkPantheress moment, like ten years ago, the internet was very different, right? You talk about this in Stay True, when the internet was a destination.

HH

Yes, there was only so much back then.

EO

You were talking about the internet being one-dimensional and you would go and spend time in one place and that was it. Now the internet’s like a filter through a filter through another filter in 2024. Even years ago, Instagram was its own architecture, had its own logic and language, right? And if you wanted to excel within that framework, you abided by its rules. And Twitter attracted a specific audience that explicitly expressed itself through words. So Twitter and Instagram and Facebook. Facebook preceded those two things and we needed something new to kind of occupy our time, which became Instagram and Twitter. But then now, fast forward 10 years later, we have TikTok and we’re in this rush to captivate and keep people’s time–there’s no such thing as being offline or ‘logging out’. Instagram is Twitter is TikTok is Facebook is LinkedIn is Cash App is Venmo. You’re on Instagram, TikTok and Twitter, on Twitter, you’re on Instagram, TikTok and Twitter, X. We lack a certain kind of specificity. And I’m curious...

HH

That flattening of experience as a critic is interesting because, going back to the context thing, I’m interested in, for example, post-George Floyd, Black Lives Matter, so many different institutions responded in different ways. Some of them quickly in an over-compensatory way, some of them slowly, and yet they’re all kind of producing these things that we can talk about. But I guess I’m always more interested in why the thing exists or what produced the thing. Even though I am a generalist, that’s why I don’t write about art as much because even though I’ve curated shows or I’m friends with curators, I don’t understand. And even though everyone considers themselves a curator in this kind of lame way, I don’t actually understand what that means. I’ll befriend an artist and they’ll be like, ‘You should come do a studio visit.’ I’m just like, What do you mean? Just come hang out in the studio?

But then that’s what curators do is they go and look at work in progress, and I don’t understand that skillset of what it means to be a real curator, right? I can put a cool poster next to this cool object I found and call myself a curator. But I’m not really a curator. So that’s why I don’t write about art. Or if I do, it’s for a friend’s gallery show or something because I am doing PR for them, and I’m acknowledging that, but I think that I don’t understand the apparatus, whenever there’s a biennial and people either love it or get mad at it. I’m like, I don’t know, how do you do that? How do you find all this stuff? This is just the generalist thing. I don’t necessarily understand the process.

EO

You didn’t enter into criticism trying to exert your opinion. It was more about trying to figure out. With curating, because people have this information and they feel they have authority on these things that they’re doing, they then think that that is all that’s required to actually do the job. Similar to you, this conversation we’re having about criticism, curators at a certain time, they’re actually planting seeds. A studio visit is a time to have a reprieve. Curators actually invested in the relations of furthering a person’s career and growing with them, they’re like a cohort. And people think that it’s just about picking work and putting it in a room.

HH

Because I’m so used to the A&R framework or the agent-editor framework, it’s easy for me to think the studio visit is just a catalog in the flesh. Like, all right, I’ll take that, but I know that that’s not true. It doesn’t happen as much now, but sometimes people will perform a kind of media criticism, where they identify something wrong with a headline. I don’t think I’ve written a headline in 15 years because I’m bad at it. Like at The New York Times, there’s people who only write headlines. So you have to understand that if you were to compare this article with this artwork, with this piece of music that they’ve come into the world through different avenues and we need to understand how they’ve come into the world. But that goes back to the generalist thing about why I think, even as it’s good that generalists are able to see these juxtapositions in larger patterns, critics still need to account for capitalism and institutions and how these things have come about. I think that we do that less because it’s less immediate to think about these things sometimes.

EO

In what sense?

HH

I’m really interested in the history of jazz criticism. And there was this moment in the late ’60s and the early ’70s where there were critics who were interested in the economics of the jazz club and how you could fold that into the criticism. Obviously it’s more immediate to try and put into words what John Coltrane sounds like. But thinking about the rooms in which this music was played and improvised, and the economics of who was in that room, and how people were paid, it’s sort of any analysis of music in 2024. It’s sort of incomplete without thinking about Spotify and how we’re sort of moving towards this discursive understanding that if you don’t make money from music, you’re either a loser or a hobbyist. And that’s just part of what it means to be creative in 2024, that there’s an interest within the industry to exploit creativity, but also to demean it and to devalue it, but it’s much harder to weave that into a piece of writing about a song or an album.

EO

To come back to this Beyoncé thing, it’s about so much more than the music at this point.

HH

But it’s much more fun as the critic to write about those things.

EO

What things?

HH

I remember Beyoncé, Radiohead...I don’t know why Radiohead came to mind. Well, the reason Radiohead came to mind is because in comparison to what the average musician can do there are people who are just able to do much more, the resources they can marshal are much greater. For whatever reason, I was thinking about when Radiohead put out In Rainbows, and they sold it directly to consumers. And people were like, this is the future. But not everyone is at that level where you could do that. I think it’s kind of the same with Beyoncé, where she has this vision, but she’s actually able to act on it, but it’s because she has these resources. But it’s much more fun to talk about the finished product than to dwell on the making of it.

EO

Yes, it’s not sexy. But also we don’t have documentaries about the process anymore. We’re not let backstage because these artists also now control and dictate the camera movement, narrative, and story.

HH

This goes back to the hollowing out of journalism, these changing attitudes toward what journalists or critics do, which has resulted in a change in what we’re allowed to do. I’m part of this initiative called Critical Minded, where we’re thinking about the future of critics and people of color and the history of magazines that are no longer here. The economic piece is so grim, I could not make a living solely as a writer. I kind of need to teach. But what does it do, going back to the thing we’re talking about with Roberta and Jerry Saltz, how does it change? What happens to the critical landscape when most critics need to do copywriting on the side or teach or adjunct or ghostwrite?

EO

What happens to them?

HH

I don’t know what happens. We live in this strange moment where I would say the critical discourse has never been more robust because there’s just more of it, but where it’s harder than ever for a working critic, like someone whose vocation is to keep track of these things and to monitor these conversations and to intervene, it’s harder than ever to actually like make a living doing that. It probably reflects a larger cultural devaluation of creativity, dissent, going back to the failure, the possibilities of failure. It’s times like this where my dumb optimism has to kick back in, because I’ve taught so many students at this point, and it reminds me of how when I was in my 20s, I thought adults hadn’t tried hard enough or adults didn’t see what I could see as a 20-year-old.

And so I have to retain faith that someone will see past what we’re pointing out. I think that’s the only way civilization has persisted, that people who are younger than me can see past what I think is possible. It might not be because I taught them that. It might even be because they hated what I taught them. But that’s the only way I can continue doing any of this work is with a sense that someone else will do it better. I always think about the influence of great artists and how it’s not necessarily the person who begins making music and mimics the style of someone great, but it’s the person who takes those ideas or those visions somewhere you couldn’t possibly foresee and hopefully does something positive with them.