The 1990s were a decade whose cultural flash points can now be readily summarized by the Twitter historian, the nostalgic TikToker, and anyone else who has processed years of received clichés into conventional wisdom. Nirvana remade rock music in the image of angst and flannel; the O.J. Simpson trial ushered in the reign of the 24-hour news cycle; the World Wide Web was slowly becoming a big deal beyond the world of nerds and losers; the travails of the Clintons polarized American politics. But surely the 1990s weren’t so easily reducible. We are a little more than 20 years removed from the final decade of the 20th century: a decade ripe for extended reappraisal as a distinct epoch of its own, yet one that is at risk of being engulfed by the hoary truisms and generalizations that reduce all historical eras into a collection of data points, rather than something that real people—many of them alive today—actually experienced.

Not if Chuck Klosterman has anything to say about it. One of the 21st century’s most prolific cultural critics, Klosterman has penned 12 books (nine nonfiction, three fiction) that have analyzed popular culture through an eternally bemused and highly skeptical lens and that have occupied plenty of real estate on the New York Times bestseller list. Klosterman got his start as an arts critic at the Akron Beacon Journal in the late ’90s, where he built a local reputation as a wry contrarian; his first book, Fargo Rock City: A Heavy Metal Odyssey in Rural North Dakota, was a memoiristic analysis of the 1980s hair-metal bands taken seriously by few other writers. After moving to New York City, where he took a job at the then-vibrant music magazine Spin, Klosterman quickly cemented himself as a premier surveyor of the mainstream. His breakthrough essay collection, 2003’s Sex, Drugs, and Cocoa Puffs, offered highbrow meditations on lowbrow phenomena like MTV’s The Real World, Guns N’ Roses cover bands, and the rivalry between the Boston Celtics and the Los Angeles Lakers, advancing a worldview in which allegedly unserious things held the key to understanding contemporary reality. (“It’s certainly no less plausible than trying to understand Kant or Wittgenstein,” he said of this outlook in that book’s introduction.)

A typical Klosterman essay endeavored to sketch out the invisible architecture uniting seemingly disparate phenomena. An essay in his 2009 book Eating the Dinosaur used the respective experiences of NBA bust Ralph Sampson and pop star Britney Spears to discuss the burden of outside expectations and how both figures were trapped by social pressures. Klosterman’s writing style—voice-y, off-the-cuff, full of referential slang—suited his pop culture interests, and his essays often integrated his personal life. This type of personality-driven, ad hoc cultural essay is no longer a novel form in the Internet era, at least partly due to Klosterman’s own influence, but he utilized it with success.

In his latest book, The Nineties, Klosterman now turns his attention to the decade that has haunted nearly all of his published work. Some of his subject matter—the music of Nirvana, the ideological merits of the Unabomber, the beguiling popularity of Bill Clinton—has popped up in previous books. But here, his purview shifts from purely critical to something more unexpected in its ambition: In The Nineties, Klosterman seeks to reconstruct what it felt like to live through the decade. In particular, he unpacks what it felt like for those legions who built their identity around the rejection of conventional society, notably in their refusal to sell out. You might recall the once pervasive concept of “selling out” as a vague pose against the professionalized mainstream, but Klosterman contends that pushing against “the unseemliness of trying too hard” was perhaps the defining mantra of ’90s life (or, at least, his). Not everyone in the ’90s was a slacker allergic to success—Klosterman is careful to specify that “the indoctrination of these attitudes had little impact on how the decade actually unspooled.” Nonetheless, he claims that “the feeling of the era, and what that feeling supposedly signified, isolates the nineties from both its distant past and its immediate future.”

Today, Klosterman tells us, we live in polarized times, but in the 1990s it was easier and more acceptable to avoid that altogether. The decade was “a period of ambivalence, defined by an overwhelming assumption that life, and particularly American life, was underwhelming. That was the thinking at the time. It is not the thinking now.” Perhaps, though for many Americans, life in the ’90s was neither underwhelming nor defined by a laissez-faire approach. It was an era of political combat, culture wars, welfare reform, the Gingrich revolution, “Don’t Ask, Don’t Tell,” the AIDS crisis, and Rodney King, and in focusing so closely on his own experiences and immediate Gen X milieu, Klosterman often bypasses the ways in which the ’90s were also defined by those who cared—maybe even too much.

Klosterman knows this: “When I write ‘it was a remarkably easy time to be alive,’ I only refer to those for whom it was, and for whom it usually is,” he notes early on. What follows is a selective travelogue of the decade, but one whose limitations are not obscured from the reader. His recollection of a halcyon era before everything sharply turned establishes a different sort of nostalgia from the garden-variety “27 Things Only ’90s Kids Remember” listicles that litter the modern Internet, where what he misses is not just Nirvana or Napster or Bill Clinton but the right to remain above it all, experiencing the culture from a distracted remove. The Nineties is a personal history, but it’s also an obituary for a period of time that we—and certainly people like Klosterman—are never getting back, even as its fashions and cultures are revived by admiring youth.

“Generation X” was the term popularized by the author Douglas Coupland in his 1991 novel Generation X: Tales for an Accelerated Culture, in which he used it to describe the detached and dissatisfied youth who sought no purchase amid the leftover excesses of the 1980s. “That Francis Fukuyama meme was floating around, and it didn’t seem strange to be entering an era that wasn’t an era,” Coupland tells Klosterman, referring to the famous “end of history” premise about the decade. “Nothing seemed to be happening in the entire culture.” Coupland’s declaration is reinforced by Klosterman, who writes that the election of George H.W. Bush in 1988, following Ronald Reagan’s eight years in office, “entrenched a sense of permanent normalcy. It was as if certain things about the production of culture had finally been figured out, and 1990 was launched from this static plateau.” Within a few years of Generation X’s appearance, Coupland’s nomenclature had become the accepted shorthand for an entire demographic of apathetic malcontents high on irony and low on effort, who saw no real difference between the Democrats and the Republicans and regarded anything corporate as the devil itself.

Klosterman includes himself in this caricature: “My experience across the nineties was comically in line with the media caricature of Generation X, almost as if I were a character from a Netflix movie set in 1994 but written and directed by a person born in 2001 who’d only learned about history by watching Primus videos,” he writes. All of which makes him potentially the right man for writing a centralized perspective of the decade, regardless of his blind spots, and much of The Nineties is dedicated to explaining how things felt from the default Gen X vantage point. Klosterman is white; he is straight; he did not vote in the 1996 election; he semi-recently joked that his ideal head of state would be “a super-lazy, super-moral libertarian despot.” In Sex, Drugs, and Cocoa Puffs, recalling his experience of both 1992 and 1994, he describes a daily lifestyle of drinking copious amounts of beer and arguing endlessly about banal cultural topics with his friends. Conspicuously, The Nineties is his least jittery book. With fewer free-floating digressions than past efforts, it’s written in a cool, neutral style bereft of the jaunty tics and arch humor with which he’s most associated, lending a veneer of gravitas.

But the book is not exactly comprehensive, and despite the concessions to objectivity in its tone and style, the framing device is clearly Klosterman’s own experience and what he found most interesting from the era. At the beginning of The Nineties, he references David Halberstam’s The Fifties and Bruce J. Schulman’s The Seventies—books that took a more methodical approach to chronicling their respective decades—as antecedents for his project. What the book more closely evokes, however, is something like Wayne Koestenbaum’s My 1980s and Other Essays, a sticky and deeply intimate account of the ’80s (even though Klosterman’s personal life is relatively missing from these pages). “I sometimes worked in reverse, searching for source material that verified what I thought I remembered,” Klosterman confirms in the bibliography. “This process worked roughly half the time.”

Ergo, most of the book’s essays rope in music or sports—subjects that track with Klosterman’s existing oeuvre. The success of Nirvana’s Nevermind, he argues, behaved as a fulcrum on which the dominant mainstream culture could be overturned, thus properly launching the slacker-­driven counterculture now associated with the ’90s. Another chapter talks about how Kurt Cobain’s obvious repulsion over his popularity turned him off the trappings of the rock star lifestyle, which, in turn, pushed his peers to reject them as well. This attitude was then taken up by country artists like Billy Ray Cyrus and Garth Brooks, who sanded down the rocker’s edge into a colorless, commercial entertainment signifying nothing but itself. Klosterman connects this shift to other pop culture phenomena: The TV show Friends and the film Titanic are other examples of hugely popular and ideologically conventional entertainment.

Elsewhere, Body Count’s “Cop Killer,” Alanis Morissette’s Jagged Little Pill, and 2 Live Crew’s As Nasty as They Wanna Be feed into a discussion about political correctness and the “phenomenon of white-bread audiences suddenly confronting ideologies that minority groups had long considered inescapable parts of life,” such as state violence (Body Count) or female rage (Alanis). This led to a recurrent phenomenon in which the cultural gatekeepers would express total confusion about the nuances of those ideologies (such as the possibility that Body Count weren’t calling for violence against all cops, as rapper Ice-T has since pointed out, simply the ones who abused their power) and strenuously push back in the press—only for the Overton window regarding permissible language to slowly shift, as consumers intuitively understood what the commentariat did not.

These are lively essays, and the fun in reading them—as with the strongest of Klosterman’s previous work—is in following the writer’s several sharp turns and unconventional connections as he nudges and inches his way toward a series of ideas that are often more interesting than they are rigorous. His lifelong focus on the so-called lowbrow pays the most dividends, as he hones ideas about the subjects covered in previous books into their final form. My disclosure, though, is that in some ways I am the ideal Klosterman reader: I entered college as his first books were becoming required reading for fans of indie rock and ESPN, and as he’s aged into this more sober yet indefinitely contrarian writer, I’ve still found pleasure in following along his thought process, nodding at the parts I agree with and disregarding the parts I don’t. This is a heavily selective way of reading, and less subjective observers (as in: the ones who didn’t discover him as impressionable teenagers) have assailed Klosterman’s work for its ramshackle arguments, its devil’s advocacy, and the casual confidence with which he insists on some ideas that are simply not true.

Klosterman runs aground most when he dips into straightforward political analysis. A lengthy dissection of Ross Perot’s third-party candidacy in the 1992 presidential election ends up positing that 20 million voters chose Perot “because it didn’t seem like a particularly big deal to do so,” an extension of his “nothing seemed to matter” theory about the decade’s overarching malaise. Maybe, but that’s 20 million voters folded into a thesis that conveniently suits what he’s already been writing about. A subsequent counterfactual about the 1992 election taking place without Perot ends up concluding that “the modern Republican Party would likely be much less extreme if George H.W. Bush had been reelected in a landslide,” because then it wouldn’t have reoriented itself in rebellion to the objectionable Bill Clinton. This is offered as a quick aside, but such a claim obviously strains credulity.

Books like The Nineties are meant to engender debate, and so I realize it’s unnecessary to challenge every single little thing that I might disagree with, but many of the book’s arguments boil down to “Take my word for it.” Klosterman is good at describing things: A series of interstitial chapters also function as straightforward primers on specific people and events he deems crucial, such as the rapper Tupac Shakur, the economist Alan Greenspan, and the author Elizabeth Wurtzel, among others. But the attempt to weave such diverse phenomena into a cogent story about the ’90s and its narratives is bound to sputter out. An essay on the decade’s crop of video store employees turned filmmakers (Quentin Tarantino, Kevin Smith, etc.) and their influence on the ascendent movie culture hits a sour note in its final lines, when Klosterman claims that by 2015, “the notion of seeing a film (or any art) as separate from real-life morality and present-day politics had become increasingly unpopular. By 2020, it was verboten.” He holds up Tarantino as a target of this modern joyless perspective, never mind that for all the director’s sniping about his morality and politics, many people are still perfectly happy to watch his movies (most recently, the widely acclaimed Once Upon a Time in Hollywood).

Another essay is dedicated to what now seems retroactively inexplicable: the stratospheric popularity of Bill Clinton, who ushered in a wave of destructive neoliberal policies and threw the presidency into jeopardy because he lied about an affair, but who was (and still is?) regarded as an august political spokesman within the Democratic Party. After a long disquisition on Clinton’s merits and demerits, the essay makes a bizarre analogy between him and the 1999 film American Beauty, which was a critical and box office success and is now regarded by some as largely embarrassing. “Almost every key point in American Beauty—dissatisfaction with a traditional livelihood, the invisible loneliness of a sexless marriage, the shame of homosexuality, the longing for one’s past, even the difficulty of buying pot—have come to represent pathetic dilemmas younger audiences consider opulent micro-concerns,” Klosterman boldly asserts.

Modern people hate American Beauty for the same reason people in 1999 loved American Beauty: It examines the interior problems of upper-middle-class white people living in the late twentieth century—the kind of people who voted for Bill Clinton twice and (perhaps) saw fragments of their own lives within the problems he created for himself. And it was, in all probability, the last time in history such problems would be considered worthy of contemplation.

One can point out, among many other things, that American filmmakers and moviegoers have never tired of films (and now, television) about the problems of white upper-middle-class people. But there’s also a slight bitterness in Klosterman’s thesis, an undercurrent of fear that the culture at large has abandoned people like him. This is where he edges dangerously close to becoming the type of writer who masks self-centered worries about his own cultural marginalization within a vague hand-waving about the kids these days. To be fair, Klosterman tries to avoid this tendency: In one passage, he notes how every single adult generation is skeptical of the young’s emergent behaviors and declares that “if new kids aren’t soft and lazy, something has gone wrong.” It’s a welcome concession, but no millennial or zoomer would claim that we are the way we are because society worked out for the best. We’re just doomed to be a product of our era, like Klosterman himself.

Despite its occasional tendentiousness, there is something reliably enjoyable about Klosterman’s discursive and digressive style, which invites disagreement but always gives you much to chew on. I enjoyed reading The Nineties because his subjective position still offers plenty of lessons on how some people experienced the era. In particular, I’ve been thinking about how Klosterman pegs the shift in national mood to the moment in 2000 when a slim conservative majority on the Supreme Court decided the result of the contested 2000 presidential election in favor of George W. Bush. “On the biggest possible stage, it was established that every sociopolitical act of the twenty-first century would now be a numbers game on a binary spectrum,” he writes. “My undefined, uncommitted Gen X worldview was instantaneously worthless. That was over. Now there were only two sides to everything.”

What’s interesting to consider here is that Klosterman’s entire national career, built around that “undefined, uncommitted Gen X worldview,” unfolded after 2000, and so this observation feels like a confession. People like him should have paid attention to what was going on politically, but they did not, because it didn’t seem to matter. His point of view was then declared worthless; nonetheless, he attempted to insert it into public consciousness over the subsequent years, to great personal success. So what explains his weariness—his sense that, in the 21st century, we’ve lost so much? It mirrors the shock of liberal voters, and in particular my Obama-voting millennial cohort, following the election of Donald Trump, at the cultural revanchism threatening to wipe out social progress we’d considered settled. If only we’d realized what was at stake, in time for someone to do something about it.

Yet the adage about hindsight being 20/20 has accrued evergreen meaning for a reason. “The compulsion to reconsider the past through the ideals and beliefs of the present is constant and overwhelming,” Klosterman writes near the end. “It allows for a sense of moral clarity and feels more enlightened. But it’s actually easier than trying to understand how things felt when they originally occurred.” Try as he might, Klosterman can only reconstruct the feeling of the 1990s so much: He is just one man with his thoughts about stuff. But Klosterman is right that someone like him is less capable of pursuing neutrality or authority in our demanding present. Everyone really does need to pick a side, including him—an uncomfortable reality for people who pride themselves on a refusal to choose.

It has never been easier to ignore the way other people live and what they pay attention to. An unoriginal observation—one that Klosterman himself believes—is that the monoculture is dead, because there are no cultural figures or products seemingly capable of galvanizing a plurality of consumers into consensus. But there are smaller-scale shared phenomena, figures and products who seem immensely important within their siloed-off realms—the Twitch streamer Ninja, the singer Phoebe Bridgers, YouTube jokesters the Try Guys, the death of Twitter—yet, at scale, only matter so much. These conditions have created a world where it will be increasingly difficult to create a comprehensive and true record of what used to matter, and how. I find it impossible to imagine what The 2020s might read like, if we’re around in 20 years to write a book about it. But I hope someone tries, so that the future might come close to understanding what’s long gone.