Underground will always be cooler than institutions. Substack is neither. So outside of a handful of craggy-brained writers (BBSP included), it is deeply cringe and uncool.
I don’t like to be a hater outside of my own head (just bc vibes), even if I anonymize the subjects of my judgement. But here I go: a lot of the big and quirky fashion and lifestyle girls on here, and some super popular newsletters about culture, are so eye roll to me. It’s mass within nothing. It’s Instagram again but with the cringe part of tumblr alongside it.
Substack is a helpful platform where I can receive what I want on my inbox. Also I like the message board aspect of it, especially the way you guys have set it up!
Having a compilation of cool things to learn about from taste makers is great (magazines, etc.) but even that is less cool than finding your own cool shit from DIY and underground sources.
I was just talking to a very cool record store owner in downtown manhattan last week. I was like “yeah I feel like I should listen to NTS more” and he was like “I try not to listen to it. It’s a cheat code, too easy. Even if I don’t listen to it I’m going to be influenced by it.”
Now NTS is obviously very cool. But even cooler is like, digging deep within labels you like. Finding some Australian DJ with crazy mixes where most songs aren’t Shazam-able. You meet a guy who reissues weird German or Dutch tapes from the 80s. Etc. extrapolate to clothes, dining, film.
Looking to “tastemakers” is the best option and helpful if you want some swag but don’t have taste. It’s also just interesting to see what everyone is doing. And sometimes you get a good tip.
But the coolest thing will always be doing your own shit.
And finally, restaurants are amazing but knowing and going to restaurants as a personality (or big part of one’s personality) isn’t cool.
Also - and not implying this is OP - if the thing you dug deep before becomes popular, don't gatekeep it. Spread the love and share the wisdom. Maybe we'll get more rad shit because of it.
So frustrating to read one of our culture’s current tastemakers describing GQ as cool and suggesting they always have been. Are we going to continue pulling the wool back on until we can say “Actually, Maxim was good”?
In 2025 it’s impossible not to see the impact of America’s regressive cultural movements filtering down into the subcultures I have called home.
We are definitely looking back toward Paul Newman, up at the tall ceilings at Balthazar, down into martinis for the same reasons white women are doing trad wife aspirations and gym bros are doing Marcus Aurelius profile pics. Btw I love Paul Newman and Balthazar and minorly fuck with Marcus Aurelius.
Hardly anything means anything anymore and most stuff sucks ass. I find it cowardly to retreat into crumbling power in response to that. Your ending saved me from being entirely pissed off about all this. Some institutions are good. Hearst tower contains none of them
I really appreciate your comment. There has always been an obsession with whiteness in this country, but there is a particularly strong and regressive one right now, and I think the takes about institutions and trends like the ones you and Jonah called out, highlight this obsession and reverence for that whiter stratified culture that existed in the pre Internet era. The people who held most power and institutions were white and rich and made sure that the culture of America was white or white-washed and dictated by THEM. I don't blame Chris and Rachel for falling into the trap, but, to me, yes they did fall into revering something supremely uncool and uninteresting because there is a zeitgeist of a desire or nostalgia for a whiter America.
This trend and statements are demonstrably uncool. Coolness is something that goes hand in hand with counter-cultural movements of oppressed people that use arts and culture as tools of resistance and imagining of other worlds. This usually manifests in racial and ethnic minorities, queer culture, working class people, etc.
These are the places where culture and arts truly advances, not in the bourgeoisie.
The term hipster originated in the 1930's and 40's to represent those who were "in the know", and it was particularly used for white kids in Harlem and Brooklyn who started participating in jazz and black culture: music, slang, fashion (zoot suits!!), etc. Obviously the word ended up being morphed into more of an image in some people's minds during the 00's and 10's: our local mustachioed, flannel-wearing, fixie riding, ..., craft brewer. But before this image was a thing, the word had evolved from referring to that jazz subculture to being a term that more generally describes cool people who were aware and involved with cool shit and were the ones that led to that thing later becoming widespread cool.
There's an aside here that is important to call out, but super deep in its own right, so I will just acknowledge it: due to the structures and powers that be of this society, even though most stuff that is cool comes from oppressed minorities, they usually only become acceptable and desirable in a more widespread way after they have passed through the white filter of the hipsters/the gentrifiers. These tastemakers don't want those things to become gentrified but the mere act of getting into these things is the first step of gentrification.
Going back to the example of where cool music has come from, we can see how the same thing that happened with jazz has happened with things like blues, hip-hop, Detroit techno and Chicago house, "world music", bossa nova, ethiopian jazz (the soundtrack of cool restaurants in the late 10's/early 20'), etc. And more importantly, even genres that are seen more traditionally as white, like rock, country, generic dance music, it all has roots in black music. Same applies to examples in other facets of the arts and culture.
So, calling traditional American institutions like GQ and Conde Nast cool seems very anti cool. If those publications had/have any coolness, it is mainly because they employ people who are those hipsters/gentrifiers who are really into stuff and share it with the world. Where does that cool stuff they write about come from? I'd argue a lot of it comes directly or is inspired by culture and art made by minority groups. Is substack cooler? Nah, it's also another corporation which cares about maximizing shareholder value, etc. High quality writers exist in either of those platforms of publication, and I think many of them are really cool. The capitalist machine and board rooms behind the institutions is not cool. Yes, there is value in how some of the magazines and newspapers cared about high quality rigorous journalism, but I don't buy the whole coolness argument.
A final aside: Rachel missed yet another group (in addition to the group of people like Papa Spyplane) in her categorization of people based on what restaurant is their personality. Those who would never be seen setting foot on either of those places mainly because they find both to be boring white people food. Given the zeitgeist, of course, the 2 possible options are old-school chic aspirational white approaches to dining. In a town like NYC, where you have one of the most diverse gastronomic landscapes in the planet thanks to it's super large migrant communities, the only time you'd see me eating at a place like either of those is when I'm forced by someone I love really really really wants to go with me to a place like that. There are people who only want it spicy ;)
Jonah, once again thanks for keeping it real and for, lovingly, calling BS where you see it.
Serendipitous essay, as I've been ruminating on this very subject a lot lately. One other thing I'll point out is that venerating institutions is ultimately a submissive act, possibly even a masochistic one. Institutions will always leverage your love for them as a negotiation tool; you acquiesce to their demands in conflict with your own code. It's in some ways a relinquishing of self-respect. I'm not saying this judgmentally, I'm equally as guilty of it in my personal and professional life. But I do believe that trying to imagine something new within increasingly restrictive technological and market forces is incredibly difficult, and it's therefore easier and more pleasurable to reenact something bygone instead.
Institutions are only sort of cool. Passion is absolutely cool.
I’ve been trying to think about why I deeply love this newsletter, when the connection seems kind of obvious: I grew up weirdly obsessed with GQ and Esquire and how writers at those magazines defined style. But the ones I actually loved were total nerds about tailoring and watch lore, in the way that Joan Didion was a nerd about California’s water supply.
People who geek out about their chosen fixation are capable of convincing you a new world is available and enviable. I think this newsletter does this. But people cannot geek out with conviction about B2B SaaS, ruthless profit margins, and gaming search engines. Many present-day media organizations try to convince writers and editors to enjoy — or at least tolerate — these things because they are the means through which they currently survive or find subscribers. This is all to say that I think this newsletter sings because it’s true and sweet and nerdy, which are key attributes of passion, which is a key attribute of beauty. Also, I worked at Big Boy as a teenager and was really passionate about it, so I think Big Boy is also beautiful and a cultural institution.
While GQ/Esquire from the 90s were extremely chauvinistic (mostly mirroring the era, but that's not an excuse), there was a genuine sense of helping to educate people in lesser known details. There's an aristocratic bearing that still feels welcoming to how it's arranged.
I've kept a GQ that was entirely football-themed since I bought it around 1999 or so; the tone of the writers is both erudite and yet often like a guy you're talking to at the bar who knows more about books than you.
And MY GOD the ads! Each issue was like 60% ads, but you can see the creativity and effort at work! In that GQ I just mentioned, there are ads that feel incredibly aspirational in a way that doesn't really happen anymore.
Old magazines were SO white, and SO devoted to gatekeeping, but they at least employed a shitload of people to make the commerce move. Something we don't really get anymore!
Maybe I'm stupid with it, but to me, the appeal of all those monoculture-aided whitehairs and 90s touchstones is that they enjoy a sort of totemic purity that comes from the fact that they were never compromised by being on or having to care about the Internet.
Being online is, frankly, humiliating. Doubly so if you have to do so in a context that requires you to "engage" with an "audience." (This chat excepted ofc.)
One more facet of the link between institutions, blessedness, and status—and/or class—that you explore here: it's not only that the old elites served as gatekeepers through the culture industry concerns they owned and ran, they were also part of the money behind the kinds of public institutions you rightly lionize in your brilliant conclusion. Whatever else we might say about them, the WASPs and the various now-old-then-new-money types who'd joined them by the middle c20 practiced philanthropy in ways that really did add to the public good in culture, art, education, etc. etc.
For the pro-social institutions you celebrate, funding comes from taxes on the one hand and foundations and whatnot on the other. That's the basis for the world where you can take the MTA not just to the airport, but also to hear the NY Phil. And so our current situation is the result of the double crises of the recession of the state and the fall of the old elites to tech money. Seems like, then, that to meet your call to save and renew pro-social institutions without (even benevolent) elites, partisans of culture will have to consider how to bring some contemporary swag to old fashioned politics and governance.
David Hammons is alive and well. Please update accordingly!
You see it in the renewed canonization of epochal GOATS still living (Bob Dylan, Martin Scorsese, David Hammons) and dead (Joan Didion, Miles Davis, Donald Judd, David Lynch, André Leon Talley).
Great essay, but the Hillstone line really rankled me. I’m down with the Plane’s version of “cool”—which reflects taste and distinction but is playful, inquisitive, fun, and kind-vibed (unless you wear no-show socks). To me, that Hillstone quote strips all that away and presents “cool” as nakedly about status. No thanks.
Rachel’s Hillstone line you mean? That’s a rankler for sure.
But I’m not sure your read is necessarily correct — or, at least, there are other reads possible (eg one is a chain devoted to a nationally duplicatable expensive comfort-food menu and air of ersatz fanciness, whereas the other is a small cozy singular neighborhood restaurant with a more personal and creatively ambitious approach to the menu, etc)
Yes, that’s the line I was referring to and perhaps I misunderstood it. (I have not heard of or been to either restaurant.) The parenthetical made it seem like the point of this whole “coolness” exercise is to laugh at the uncool. But I may be missing the playfulness.
For some reason, that line brought to my mind two types of “cool” kids that I recall from middle school (when I was decidedly uncool.) One kind of cool kid had a charisma and vibe that kind of made you feel cooler yourself when you interacted with them; another kind of cool kid made you very aware of how uncool you were. The Plane really reminds me of the former, and that Hillstone line evoked the latter.
Parallels what’s happened to our government since the 80s. Shrink our government and shrink our institutions for the sake of efficiency has left our country with crumbling bridges and roads and no social safety net.
Thank you. I am a magazine journalist who started in the late 90s, and it’s just sad, sad, sad most of the time, but your letter is one of those gleams of light. I want to make a zine, just to feel like I am doing something real!
BBSP Nation might enjoy Joseph Pieper's "Leisure: The Basis of Culture" as we explore the current collision of media saturation meets influencers meets the petrification of creativity upon gaze of AI, as we all grasp for the collapsing staves of our society.
I had bookmarked this from his book:
“A man who needs the unusual to make him "wonder" shows that he has lost the capacity to find the true answer to the wonder of being. The itch for sensation, even though disguised in the mask of Boheme, is a sure indication of a bourgeois mind and a deadened sense of wonder.”
I woke up feeling really blocked about working on the book I’m writing, then read this essay & felt encouraged & ALIVE with words… so thank you very much!! Consistently inspired by the Plane🌱
Underground will always be cooler than institutions. Substack is neither. So outside of a handful of craggy-brained writers (BBSP included), it is deeply cringe and uncool.
I don’t like to be a hater outside of my own head (just bc vibes), even if I anonymize the subjects of my judgement. But here I go: a lot of the big and quirky fashion and lifestyle girls on here, and some super popular newsletters about culture, are so eye roll to me. It’s mass within nothing. It’s Instagram again but with the cringe part of tumblr alongside it.
Substack is a helpful platform where I can receive what I want on my inbox. Also I like the message board aspect of it, especially the way you guys have set it up!
Having a compilation of cool things to learn about from taste makers is great (magazines, etc.) but even that is less cool than finding your own cool shit from DIY and underground sources.
I was just talking to a very cool record store owner in downtown manhattan last week. I was like “yeah I feel like I should listen to NTS more” and he was like “I try not to listen to it. It’s a cheat code, too easy. Even if I don’t listen to it I’m going to be influenced by it.”
Now NTS is obviously very cool. But even cooler is like, digging deep within labels you like. Finding some Australian DJ with crazy mixes where most songs aren’t Shazam-able. You meet a guy who reissues weird German or Dutch tapes from the 80s. Etc. extrapolate to clothes, dining, film.
Looking to “tastemakers” is the best option and helpful if you want some swag but don’t have taste. It’s also just interesting to see what everyone is doing. And sometimes you get a good tip.
But the coolest thing will always be doing your own shit.
And finally, restaurants are amazing but knowing and going to restaurants as a personality (or big part of one’s personality) isn’t cool.
Also - and not implying this is OP - if the thing you dug deep before becomes popular, don't gatekeep it. Spread the love and share the wisdom. Maybe we'll get more rad shit because of it.
Full agree!
Best comment I've read on substack. If you don't already, you should write.
wow thank you! I actually just started a newsletter :) it's about pelvic health, not culture though.
So frustrating to read one of our culture’s current tastemakers describing GQ as cool and suggesting they always have been. Are we going to continue pulling the wool back on until we can say “Actually, Maxim was good”?
In 2025 it’s impossible not to see the impact of America’s regressive cultural movements filtering down into the subcultures I have called home.
We are definitely looking back toward Paul Newman, up at the tall ceilings at Balthazar, down into martinis for the same reasons white women are doing trad wife aspirations and gym bros are doing Marcus Aurelius profile pics. Btw I love Paul Newman and Balthazar and minorly fuck with Marcus Aurelius.
Hardly anything means anything anymore and most stuff sucks ass. I find it cowardly to retreat into crumbling power in response to that. Your ending saved me from being entirely pissed off about all this. Some institutions are good. Hearst tower contains none of them
I really appreciate your comment. There has always been an obsession with whiteness in this country, but there is a particularly strong and regressive one right now, and I think the takes about institutions and trends like the ones you and Jonah called out, highlight this obsession and reverence for that whiter stratified culture that existed in the pre Internet era. The people who held most power and institutions were white and rich and made sure that the culture of America was white or white-washed and dictated by THEM. I don't blame Chris and Rachel for falling into the trap, but, to me, yes they did fall into revering something supremely uncool and uninteresting because there is a zeitgeist of a desire or nostalgia for a whiter America.
This trend and statements are demonstrably uncool. Coolness is something that goes hand in hand with counter-cultural movements of oppressed people that use arts and culture as tools of resistance and imagining of other worlds. This usually manifests in racial and ethnic minorities, queer culture, working class people, etc.
These are the places where culture and arts truly advances, not in the bourgeoisie.
The term hipster originated in the 1930's and 40's to represent those who were "in the know", and it was particularly used for white kids in Harlem and Brooklyn who started participating in jazz and black culture: music, slang, fashion (zoot suits!!), etc. Obviously the word ended up being morphed into more of an image in some people's minds during the 00's and 10's: our local mustachioed, flannel-wearing, fixie riding, ..., craft brewer. But before this image was a thing, the word had evolved from referring to that jazz subculture to being a term that more generally describes cool people who were aware and involved with cool shit and were the ones that led to that thing later becoming widespread cool.
There's an aside here that is important to call out, but super deep in its own right, so I will just acknowledge it: due to the structures and powers that be of this society, even though most stuff that is cool comes from oppressed minorities, they usually only become acceptable and desirable in a more widespread way after they have passed through the white filter of the hipsters/the gentrifiers. These tastemakers don't want those things to become gentrified but the mere act of getting into these things is the first step of gentrification.
Going back to the example of where cool music has come from, we can see how the same thing that happened with jazz has happened with things like blues, hip-hop, Detroit techno and Chicago house, "world music", bossa nova, ethiopian jazz (the soundtrack of cool restaurants in the late 10's/early 20'), etc. And more importantly, even genres that are seen more traditionally as white, like rock, country, generic dance music, it all has roots in black music. Same applies to examples in other facets of the arts and culture.
So, calling traditional American institutions like GQ and Conde Nast cool seems very anti cool. If those publications had/have any coolness, it is mainly because they employ people who are those hipsters/gentrifiers who are really into stuff and share it with the world. Where does that cool stuff they write about come from? I'd argue a lot of it comes directly or is inspired by culture and art made by minority groups. Is substack cooler? Nah, it's also another corporation which cares about maximizing shareholder value, etc. High quality writers exist in either of those platforms of publication, and I think many of them are really cool. The capitalist machine and board rooms behind the institutions is not cool. Yes, there is value in how some of the magazines and newspapers cared about high quality rigorous journalism, but I don't buy the whole coolness argument.
A final aside: Rachel missed yet another group (in addition to the group of people like Papa Spyplane) in her categorization of people based on what restaurant is their personality. Those who would never be seen setting foot on either of those places mainly because they find both to be boring white people food. Given the zeitgeist, of course, the 2 possible options are old-school chic aspirational white approaches to dining. In a town like NYC, where you have one of the most diverse gastronomic landscapes in the planet thanks to it's super large migrant communities, the only time you'd see me eating at a place like either of those is when I'm forced by someone I love really really really wants to go with me to a place like that. There are people who only want it spicy ;)
Jonah, once again thanks for keeping it real and for, lovingly, calling BS where you see it.
Appreciate the kind words & extended meditation
Serendipitous essay, as I've been ruminating on this very subject a lot lately. One other thing I'll point out is that venerating institutions is ultimately a submissive act, possibly even a masochistic one. Institutions will always leverage your love for them as a negotiation tool; you acquiesce to their demands in conflict with your own code. It's in some ways a relinquishing of self-respect. I'm not saying this judgmentally, I'm equally as guilty of it in my personal and professional life. But I do believe that trying to imagine something new within increasingly restrictive technological and market forces is incredibly difficult, and it's therefore easier and more pleasurable to reenact something bygone instead.
Too true
Institutions are only sort of cool. Passion is absolutely cool.
I’ve been trying to think about why I deeply love this newsletter, when the connection seems kind of obvious: I grew up weirdly obsessed with GQ and Esquire and how writers at those magazines defined style. But the ones I actually loved were total nerds about tailoring and watch lore, in the way that Joan Didion was a nerd about California’s water supply.
People who geek out about their chosen fixation are capable of convincing you a new world is available and enviable. I think this newsletter does this. But people cannot geek out with conviction about B2B SaaS, ruthless profit margins, and gaming search engines. Many present-day media organizations try to convince writers and editors to enjoy — or at least tolerate — these things because they are the means through which they currently survive or find subscribers. This is all to say that I think this newsletter sings because it’s true and sweet and nerdy, which are key attributes of passion, which is a key attribute of beauty. Also, I worked at Big Boy as a teenager and was really passionate about it, so I think Big Boy is also beautiful and a cultural institution.
While GQ/Esquire from the 90s were extremely chauvinistic (mostly mirroring the era, but that's not an excuse), there was a genuine sense of helping to educate people in lesser known details. There's an aristocratic bearing that still feels welcoming to how it's arranged.
I've kept a GQ that was entirely football-themed since I bought it around 1999 or so; the tone of the writers is both erudite and yet often like a guy you're talking to at the bar who knows more about books than you.
And MY GOD the ads! Each issue was like 60% ads, but you can see the creativity and effort at work! In that GQ I just mentioned, there are ads that feel incredibly aspirational in a way that doesn't really happen anymore.
Old magazines were SO white, and SO devoted to gatekeeping, but they at least employed a shitload of people to make the commerce move. Something we don't really get anymore!
Vanity Fair Italy is a - weekly - publication. Blew my mind. Americans just aren't reading magazines at the rate of our Euro-pals.
Print industry is still huge in Japan too. Americans just have bad priorities
Chris Black isn't cool
Maybe I'm stupid with it, but to me, the appeal of all those monoculture-aided whitehairs and 90s touchstones is that they enjoy a sort of totemic purity that comes from the fact that they were never compromised by being on or having to care about the Internet.
Being online is, frankly, humiliating. Doubly so if you have to do so in a context that requires you to "engage" with an "audience." (This chat excepted ofc.)
yeah for sure, i invoke their pre-internetness in the piece along these exact lines
One more facet of the link between institutions, blessedness, and status—and/or class—that you explore here: it's not only that the old elites served as gatekeepers through the culture industry concerns they owned and ran, they were also part of the money behind the kinds of public institutions you rightly lionize in your brilliant conclusion. Whatever else we might say about them, the WASPs and the various now-old-then-new-money types who'd joined them by the middle c20 practiced philanthropy in ways that really did add to the public good in culture, art, education, etc. etc.
For the pro-social institutions you celebrate, funding comes from taxes on the one hand and foundations and whatnot on the other. That's the basis for the world where you can take the MTA not just to the airport, but also to hear the NY Phil. And so our current situation is the result of the double crises of the recession of the state and the fall of the old elites to tech money. Seems like, then, that to meet your call to save and renew pro-social institutions without (even benevolent) elites, partisans of culture will have to consider how to bring some contemporary swag to old fashioned politics and governance.
Noblesse oblige on Life Support !
David Hammons is alive and well. Please update accordingly!
You see it in the renewed canonization of epochal GOATS still living (Bob Dylan, Martin Scorsese, David Hammons) and dead (Joan Didion, Miles Davis, Donald Judd, David Lynch, André Leon Talley).
Never been so happy to make a correction. Macabre mistake. Thank you
Great essay, but the Hillstone line really rankled me. I’m down with the Plane’s version of “cool”—which reflects taste and distinction but is playful, inquisitive, fun, and kind-vibed (unless you wear no-show socks). To me, that Hillstone quote strips all that away and presents “cool” as nakedly about status. No thanks.
Rachel’s Hillstone line you mean? That’s a rankler for sure.
But I’m not sure your read is necessarily correct — or, at least, there are other reads possible (eg one is a chain devoted to a nationally duplicatable expensive comfort-food menu and air of ersatz fanciness, whereas the other is a small cozy singular neighborhood restaurant with a more personal and creatively ambitious approach to the menu, etc)
But yes the “aww cute” is patently, if playfully… antagonistic
Yes, that’s the line I was referring to and perhaps I misunderstood it. (I have not heard of or been to either restaurant.) The parenthetical made it seem like the point of this whole “coolness” exercise is to laugh at the uncool. But I may be missing the playfulness.
For some reason, that line brought to my mind two types of “cool” kids that I recall from middle school (when I was decidedly uncool.) One kind of cool kid had a charisma and vibe that kind of made you feel cooler yourself when you interacted with them; another kind of cool kid made you very aware of how uncool you were. The Plane really reminds me of the former, and that Hillstone line evoked the latter.
🥲🙏🏻
The only cool institution remaining today is the plane, baby.
P.S please put me on the OT list
Awesome read.
Parallels what’s happened to our government since the 80s. Shrink our government and shrink our institutions for the sake of efficiency has left our country with crumbling bridges and roads and no social safety net.
Damn… Is there a better feeling than having your suspicions validated in a more coherent, legible way than you could have articulated yourself?
Thank you. I am a magazine journalist who started in the late 90s, and it’s just sad, sad, sad most of the time, but your letter is one of those gleams of light. I want to make a zine, just to feel like I am doing something real!
Make that zine! Let me send you mine :)
BBSP Nation might enjoy Joseph Pieper's "Leisure: The Basis of Culture" as we explore the current collision of media saturation meets influencers meets the petrification of creativity upon gaze of AI, as we all grasp for the collapsing staves of our society.
I had bookmarked this from his book:
“A man who needs the unusual to make him "wonder" shows that he has lost the capacity to find the true answer to the wonder of being. The itch for sensation, even though disguised in the mask of Boheme, is a sure indication of a bourgeois mind and a deadened sense of wonder.”
!
Need to check this book out. That quote goes hard
I woke up feeling really blocked about working on the book I’m writing, then read this essay & felt encouraged & ALIVE with words… so thank you very much!! Consistently inspired by the Plane🌱
Goddamn, this is it! Thanks for writing and sharing.