WHO KILLED COOL? AND WHAT DO WE CHASE NOW...

Sincerely, isn't it ironic?

My interest in unpacking this topic began in mid-July, when I attended Dazed’s Death of Cool webinar, stumbled upon Edmond Lau’s Irony-Sincerity Cycle post, and learned of viral Superman Hopecore content. I immediately felt these ideas intersected, and decided I wanted to write about this, as mentioned in my Trend Radar from July 21st. 🫠

So, this one has been in drafts for three months now: an impenetrable knot festering somewhere in the back of my brain, getting gnarlier by the week and increasingly difficult to disentangle. Turns out that I mostly just needed a bit of a break. Luckily, I’m blessed to be a Libra, so I spent last week in the desert and bricked my phone.¹

Hope you enjoy the fruits of my birthday detox!

A quite literal representation tbh

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Whether as a consumer or a brand, we’re all chasing cool. ²

The provocation that cool may be dead is startling: Who killed it? If cool is dead, are trends dead? Is irony dead, too? And is that why, apparently, sincerity is back? Should we all chase earnestness now?

Dazed’s report, and a followup essay on The Collapse of Cool by Amy Francombe, both argue that cultural products are cycling from cool-to-commodified at ever-increasing speeds, leading to death/collapse (aka marketing + social media killed cool). They conclude by suggesting the way forward is emphasizing qualities like presence over clout, heritage instead of hype, and sustainability and care rather than overconsumption and apathy. This seems to align with Edmond Lau’s Irony-Sincerity Cycle, and a later piece from barr balamuth asking, Is it Cool to Care Again?

The takeaway is fairly clear: sincerity is back and we’re re-entering an era of earnestness. But I’ve had a nagging feeling that our current cultural climate seems more complicated than that. How can we be in the sincerity section of the cycle, if the cycle of cool itself has already collapsed?

I’m proposing that our embrace of the irony-sincerity cycle has played a significant conspiratorial role in the demise of cool. Simply reverting to sincerity is futile because the collapsed cycle of commodification will commercially exploit this earnestness before it even has time to properly take hold. And chasing cool, following the course of these cycles, may no longer be a viable strategy. But a better understanding of how we got here can potentially help us navigate our way out.

This essay is long. If you’re impatient, feel free to skip down to Post-Cool Strategies.

Origins of Cool

Dazed’s Death of Cool report begins by summarizing the roots of cool: The origins of its modern meaning “trace back to West African traditions, where concepts like ‘itutu’ (Yoruba for ‘coolness’) symbolized spiritual composure, grace under pressure, and quiet strength.” This concept was later leveraged by African Americans, who used coolness “as a coded survival mechanism — a way to maintain dignity, expression, and inner sovereignty under oppressive conditions.” Finally, the slang word ‘cool’ was popularly adopted via jazz artists like Thelonious Monk, Miles Davis, and Lester Young.

Although it’s a bit of a tangent, I think it’s incredibly important to dig further into this history, because it helps us decipher the original meaning of ‘cool’ and encourages us to confront the fact that coolness has always been deeply political.

Professor Joel Dinerstein has dissected how ‘cool’ was birthed from racial tension: the “demise of minstrelsy” overlapped with the rise of jazz in the 1920s. At this time, success was contingent on playing the role of the “entertainer” without transgressing expectations of racial subordination. Early breakout star Louis Armstrong has been derided by critics like Gerard Early as a “one-man revival of minstrelsy without the blackface.” While later stars, like Miles Davis, loathed Armstrong’s acquiescence to “clowning,” Dinerstein’s historical hindsight is more empathetic:

Hiding one’s feelings under the grinning black mask was a survival skill of great importance to all black males up through World War II; a black man could get lynched for pretending to be on equal terms with a white man under almost any circumstances.

A confluence of sociopolitical factors helped slowly relieve the necessity of concealing artistic expression behind a smiling facade, or at least created a sense of frustration with being forced to uphold this mask. But in its place, Dinerstein proposes, a new mask was conceived: coolness.

Politics of Cool

When Lester Young came onto the jazz scene in the 1930s, he actively rejected the problematic legacy of minstrelsy and instead developed a language of ‘cool,’ which fused his unique style of artistry (relaxed, smooth, flowing, light) with “new self-presentation strategies” communicated via his choice of dress (like wearing sunglasses), and behavioral demeanor (including how he held instruments). Coolness, for Young, was a quiet protest, or “actionality turned inward.”

This sensibility of coolness was further leveraged by the following generation of jazz musicians in the 1940s-1950s, including Charlie Parker, Thelonious Monk, and particularly Miles Davis. Unlike Young, this post-war generation was more aggressive in articulating cool as protest — in the rebellious spirit of their bebop musical style, by refusing to engage with their audiences, and even via vocalizing their dissent.³ Coolness, for Davis, found power in heightened tension: combining energetic artistic self-expression with restrained emotional self-composure.

Dinerstein positions the conception of coolness — in its “refusal of both acceptance and accommodation” and “ rebellious semiotics of hiding in plain sight” — as “covert preparation for a more overt [political] action.”

Miles Davis recorded The Birth of Cool in 1949-1950, and Rosa Parks sparked the Montgomery Bus Boycott in 1955.

Calling the rise of cool “a three-front cultural civil war,” Dinerstein further delineates its core elements as follows:

1. The necessary creation of “a unique, individual style (or sound) that communicates something of your inner spirit,” rebelling against “a society that rarely saw African Americans as individuals”

2. The relaxed attitude maintained in performance of any kind (grace under pressure), “tracing to West African sociocultural functions of music and dance”

3. The ‘cool mask,’ an aesthetic ‘front’ worn as as “invisible armor to hold off the prejudice, irrationality, and hostility of the society”

Crisis of Cool

Reflecting on the origins of cool — conceived as a strategic device at the intersection of artistic expression and progressive protest — makes it remarkably clear that we have lost the plot. We already feel this, having just had an egregiously uncool summer. While it’s convenient (and partially true) to pin the blame for cool’s demise on ever-faster cycles of capitalist commodification enabled by technology and marketing, this overlooks a more fundamental issue:

Cool’s aesthetic facade of ironic restraint has been divorced from its earnest creative spirit and sincere sociopolitical rebellion.

I’m not sure that we can entirely blame commodification for this divorce, because we have been complicit in our willingness to consume this stripped down, meaningless, empty interpretation of cool. We wanted the effect of coolness, without the effort.⁴

Earlier evolutions of coolness — meaning historical subcultures that we might define as cool, like hippies and punks — incorporated those elements of creative spirit and sociopolitical rebellion, constructing their own aesthetics of coolness atop a core set of shared values and beliefs. But over the past several decades, the essence of cool, originally rooted in “quiet strength” and “inner sovereignty” has undergone a series of distortions and mutations, eventually devolving into a contemporary language of coolness ostensibly defined by unhinged irony and dispassionate detachment. Somehow, a Chaos Culture, of memes, ragebait, contrarianism, and absurdity, came to be claimed as the forefront of ‘cool.’

In an essay earlier this year, Alexi Gunner acknowledges irony and detachment as strategic choices that young people have adopted “as a coping mechanism; a way to psychologically shelter themselves from the constant hardships and guaranteed failures of modern life.” This isn’t exactly a new coping mechanism for disaffected youth, but prior waves of ‘irony as cool,’ like 90’s slacker apathy, or 00’s emo teens, seem relatively innocuous in comparison to today’s particularly nihilistic sensibility.

Gunner describes this landscape as an “irony epidemic,” positioning “satire as a cultural sedative” that threatens us “losing more than just the ability to be serious,” but in fact “losing the capacity to sincerely engage — not just with art, but with life.”

Irony Killed Cool

One of the most crucial distinctions is how the current posture of ‘irony as cool’ has infiltrated the American political sphere with tangibly regressive consequences. As Joshua Citarella writes, “Ironic propaganda functions the same as real propaganda. Ironic voting is just voting.” The true irony here, in my opinion, is the disturbing realization of how our culture has managed to distort coolness, a concept originating in Black musicians’ rebellion against oppression, into a mutated form of ironic contrarianism that has been leveraged to weaponize racism and xenophobia, most perversely propelled by ‘artists’ chasing ‘coolness.’

Ironic contrarianism served as the rotten roots of the Dimes Square scene, whose key figures desperately chased ‘coolness’ by rebelling against ‘woke culture,’ which they perceived as ‘mainstream.’ Obviously, given the complex history of cool, this reading of ‘coolness’ as simply ‘anti-mainstream’ is laughably simplistic and woefully superficial. In antiart’s proclamation of the Death of Dimes Square, he explains how the scene’s attempt to project ‘coolness,’ without any cohesive foundation of moral values or artistic ingenuity, eventually collapsed under the weight of its own facade:

“The commentary and the hanging out came first. Then the art was made as an excuse to justify its existence. This lack of purpose also led to weird Thiel-adjacent right-wing influencing forces rearing their ugly heads in the form of venues like Sovereign House. Clout became the most valuable currency, so misaligned morals and principles took a sideline...Clout became more important than trying to make a statement.”

From the Red Scare podcast duo to “post-woke” fashion designer Elena Velez,’ these provocateurs’ thirst for clout via ironic edgelording at the expense of artistic integrity eventually stalled after last year’s election proved their chosen ‘contrarian’ position actually aligned with the country’s most blatantly mainstream consumer.

Perhaps fitting, then, that Dimes Square’s time of death is marked by an H&M t-shirt, “the last stop on the train of culture,” as antiart writes:

It’s like a headstone for cool. Except, H&M is giving the scene too much credit. Because it was never, ever cool.

Commodification Killed Irony

In January I wrote about Chaos Culture, and by August I wrote about Chaos Overload, noting our collective exhaustion with meme-ified marketing and productized gimmicks, including “Krispy Kreme Crocs, breast milk ice cream, and country fried hair.” While these brands are clearly attempting to tap into the unhinged irony and nihilistic humor that they see young people expressing online, the co-option of these postures to be turned into products effectively destroys any sense of ‘cool’ they may have once imparted.

The objective of these increasingly bizarre Chaos Culture branded gimmicks isn’t to generate ironic tension, but to generate a spectacle of absurdity — referencing the visual and verbal language of contemporary online irony for the sake of attention. In a ZINE essay last week, Matt Klein and Remi Carlioz propose that, “When Balenciaga sells a luxury trash bag for $1,790, they’re not creating Camp. They’re pre-ironizing their own product, baking the joke into the commodity itself.”

You can’t satirize something that’s already satirizing itself.

ZINE notes that this pre-ironization strategy comes from the collapse of reflective distance — a consequence of “the immediacy of our digital networks and global participation”— which has created an environment in which “no meaningful aesthetic, language, moment or movement can mature and stabilize.”

This “distance” has always been closing. It’s just infinitesimal now.

This thesis on how the “collapse of distance” has killed irony runs in striking parallel to Amy Francombe’s piece on The Collapse of Cool.

There is no longer a gap between cool and capital.

The triangulation of commodification, irony, and cool has left us with a sense of emptiness: “cool has curdled into a hollow parody in today’s cult of detachment.”

Earnestness is a False Promise

As mentioned at the start, the overall sentiment seems to be that we are entering a new era of earnestness. Edmond Lau’s Irony-Sincerity cycle clearly points to sincerity as the natural successor of irony, as does the Dazed Report, which argues that “For the next generation, cool isn’t about status, distance, or polish, it’s about authenticity, alignment and intention.”

Writing for the The New Yorker, Kyle Chayka wondered whether “it could be that millennial sincerity is tiptoeing back into fashion,” and for The Sociology of Business, barr balamuth concluded that, “Suddenly, caring openly, and trying hard, feels aspirational, not embarrassing.” In a recent piece called From Irony to Earnestness, Post-Culture by Sibling Studio proposes that it’s a bit more nuanced, suggesting “meta-sincerity; embracing earnestness in full awareness that it may look cringe. Rather than a naïve return to sincerity, it is a conscious choice to care, try, or feel despite knowing that detachment is the safer cultural posture.”

The early manifestations referenced are all heartwarming: a resurgence of hobbies like knitting and chess, Timothée Chalamet’s SAG Awards speech, the enthusiastic reception to Superman’s earnestness and the viral hopecore content that followed.

Unfortunately though, I’m doubtful that this shift to sincerity has staying power.

I think there are some confounding factors here:

1. SINCERITY LOST ITS COOL

As discussed earlier, sincere protest and earnest creativity were once a critical elements of cool’s quiet rebellion, but we’ve problematically stripped the concept of this original soul and spirit. Instead, our contemporary culture defines coolness as an aesthetic facade of ironic detachment. Reverting back to simple sincerity doesn’t solve the issue — we need to entirely resurrect cool.

2. THE CYCLE HAS COLLAPSED (COMMODIFICATION KILLED SINCERITY, TOO)

A similar posture of earnestness was culturally tested very recently, meaning it’s already been commodified — the “purpose-led” brand playbook is ready to go, just rollback those DEI rollbacks. A similar revival of sincerity would likely be commercialized at a breakneck pace. The cool cycle is not just faster, it’s flattened into a straight line. The pendulum is swinging so aggressively it’s about to fall apart — we need to stop chasing cool.

Post-Cool Strategies

So, who killed cool? It’s complicated — we’re all complicit in the true-crime triple homicide of cool, irony, and sincerity. Here are my suggestions for what comes next:

Resurrecting Cool is primarily a project for artists, creatives, and the general public. I don’t think brands can play a role here (commodification has killed enough!!!), but please do let me know if you disagree. I think there is an opportunity to rehabilitate sincerity as subversive (make Subversive Sincerity my next macrotrend, please).⁵ Consider strategies for ideating out-of-sight and building off-the-grid, like Offline Escape, Algorithmic Evasion, and ZINE’s Camouflage Culture.

Here ideas, aesthetics, and movements can finally fester, illegible to the dashboard. Camouflage is encrypted, niche, and resistant to capture. Invisible to brands, metrics and algorithmic capture…Camo is strategic opacity, obfuscation and resistance: culture that refuses to be easily readable, trackable, or sellable.

Stop Chasing Cool means stepping off the hamster wheel. It’s going to take a while to resurrect cool, and in the interim it’s a good time to do some inward reflection. Identify or reconnect with your values and principles, maintain conviction in your unique perspective, and pour energy into creative expression. Brands could benefit from those prompts, but may want to consider strategies that offer alternative approaches for maintaining cultural relevance, like my Macrotrend Framework, which you may have realized is not cyclical for a reason!

Addendum: Trend Bipolarity is a working theory for how to think about trends in the post-cool era, published as a follow-up to this essay.

TREND BIPOLARITY :: AFTER THE TREND CYCLE

1. I’m on a 200+ hour streak without social media apps on my phone and I would highly recommend! This stupid piece of plastic is effective — I left it in the rental car the entire week, making it extra annoying to access. The intermittent waves of feeling what I can only describe as a sort of addiction withdrawal have been wild.

2. Popular understanding of trends might suggest that they reflect what culture defines as ‘cool’: what’s on-trend is cool; and what’s off-trend is uncool. Of course, it’s not that simple, or we’d have no need for the macrotrend framework. Still, my point is, if you care about trends, then you probably care about ‘cool’, and vice-versa.

3. When asked why he didn’t interact with his audience, Miles Davis reportedly told one nightclub owner: ‘‘The white man always wants you to smile, always wants the black man to bow. I don’t smile and I don’t bow. OK? I’m here to play music. I’m a musician.’’

4. Adding some further thoughts based on constructive reader comments! — 1) Social media’s flattening of ideas-into-images has likely played a part in young people’s misunderstanding of cool as superficial aesthetic divorced from a fully embodied artistic, emotional, and political approach to moving through the world. 2) The shift from “selling out” being a slur to being the goal has accelerated the demise of cool. I think we (as a society) forgot why selling out was once considered ‘uncool.’ It isn’t simply that ‘money is bad.’ When we see a really incredible artist finally get their flowers, we cheer them on. The problem is that ‘selling out’ too early inhibits the creative incubation period that is necessary to create something truly cool. When ‘selling out’ became the goal, it contributed to speeding up the cycle. This brings us to, why did ‘selling out’ become the goal? Spiraling economic disparity made it an attractive choice. With the exorbitant cost of living in those cities that are conducive to fostering artistic communities, how do artists survive without capitalizing on the art?

5. Is Zohran Mamdami an example of Subversive Sincerity? Keeps his calm when provoked, pushes for creative ideas, oozes earnestness…one to watch