Walter Kirn ’83 lives in a converted bunkhouse on a side street in Livingston, Montana.

The bedrooms and living room occupy the entire second floor, but owing to the way the house is organized, the kitchen, as well as a bathroom and his office are on the first floor, in what was once an old storefront, and are inaccessible from the rest of the house. Whenever he or his wife want to get something from the refrigerator or a book from Kirn’s desk — in rain, snow, freezing cold, or dead of night — they must go outside, walk a few feet down the sidewalk to their “other” front door, then reverse the steps going back. 

Surely, there’s a metaphor in here somewhere. Let’s start with a project that Kirn, a prolific columnist and the author of eight books, is now finishing, one that has been percolating in his brain throughout the pandemic. Called The Last Road Trip, it details a 2½-month journey he made across the country in 2018. It is scheduled to be published by Liveright, an imprint of W.W. Norton, at a date to be determined once he completes the manuscript. 

Four years and counting is a long time for him to work on a book, Kirn admits. COVID had a lot to do with that, but the “investigative travelogue” is a new genre for him and has taken some getting used to. He was also sidetracked caring for his father, Walter Kirn ’60, who died of ALS in 2020.

“For me, the real tension in the country is between the people who feel condescended to and the people who feel unjustly accused of condescending to them.”

The road trip in search of America has been done, of course, by Alexis de Tocqueville, John Steinbeck, and many others, but Kirn was unafraid to insert himself into such company. In the same spirit as some of his literary predecessors, he wanted to learn if the country really looked like the picture that was being fed to him on cable TV and social media. He wanted to see, in other words, “if there was anything to be surprised by.” 

These are not new concerns for a writer who has mined overlooked corners of American life throughout his career. Recently, he has even been touted as a champion of “flyover country” (a term coined by his ex-father-in-law, writer Thomas McGuane) and become a regular on Greg Gutfeld’s late-night talk show. You and your friends might not watch Gutfeld, which airs on Fox, but he routinely outdraws Stephen Colbert, Jimmy Kimmel, and Bill Maher. Ever the outsider, ever the insider, Kirn perceives that there are many things we no longer know about each other. In his view, much of modern America — the seemingly unbridgeable divide between left and right, blue states and red states, and perhaps even between elite universities such as Princeton and the rest of the country — might be likened to a house in which the rooms no longer connect to each other, separated by a wall, with no door between them.

Is that too glib? If it is, Kirn seems up for the discussion. “No one,” he laughs, “intellectualizes more than a literary critic on a road trip.” 

Four years after he returned from the road, Kirn recounts his journey while comfortably seated in his first-floor study, his desk strewn with papers including another of his recent projects, an introduction to his friend Quentin Tarantino’s novelized version of the film Once Upon a Time in Hollywood. Two of Kirn’s own novels, in fact, Thumbsucker and Up in the Air, have been made into movies. He moves comfortably in celebrity circles, with another residence in Las Vegas and a family ranch in the hills above Livingston where Michael Keaton and Tom Brokaw are neighbors.

Despite the comforts of home, Kirn enjoys the road, so much that when he worked in Los Angeles, he would often drive there from Montana, nearly 2,400 miles roundtrip. Though it would not be called a travel book, the most personal of Kirn’s journeys was the one he wrote about in Lost in the Meritocracy (published in 2009), which concerned his spiritual and intellectual trip from rural Minnesota to Princeton. On one level, it is a scathing sendup of Kirn’s attempt to master the rat’s maze of standardized tests that got him into the University and opened a future of wealth and accomplishment. “I was the system’s pure product,” he wrote, “sly and flexible, not so much educated as wised up.” 

But the book is also a story of the tension between belonging and standing apart. Though he fit in chameleonlike with his striving classmates, Kirn managed to critique the meritocracy as well as join it. He arrived on campus after spending his freshman year at Macalester College but, unusual for a transfer student, was also a Princeton legacy. Kirn’s father, a patent lawyer for 3M, converted the family to Mormonism in the early 1970s and moved them to the tiny town of Marine on St. Croix, Minnesota, where Kirn grew up. (Kirn has since left the church.) The switches, Kirn wrote of his father, were “just one more phase in his campaign against convention and conformity.” In that respect, at least, the apple did not fall far from the tree.

Kirn at his home in Livingston, Montana
THE WRITER’S BLOC Kirn is trying to connect the dots of America in writing The Last Road Trip from his disconnected home in Livingston, Montana.
Photo: Erik Petersen

As a Princeton undergraduate, Kirn relied on “[f]lexibility, irony, self-consciousness, [and] contrarianism” to survive. He fought with his snooty roommates, joined “bitterly nonconformist” Terrace Club, and majored in English, submitting a 22-page collection of poems as his senior thesis. (“It’s rather thin, isn’t it?” he recalls his adviser, Joyce Carol Oates, remarking when he turned it in.) For all the tension and angst he experienced, the University served Kirn well. “A diploma ... was the least of what Princeton had to offer,” he wrote in one trenchant passage; “The major payoff was front-row seats. To everything.”

Was it ever. Former Provost Neil Rudenstine ’56 noticed Kirn and got him an interview for a Keasbey Scholarship and a spot at Oxford. Returning to New York after two years in England, Kirn toyed with the idea of becoming a playwright before publishing his first book, a collection of short stories, in 1990. Since then, he has moved between fiction and nonfiction, while also writing for some of the country’s most prestigious periodicals, including The Atlantic, New York Magazine, GQ, Esquire, Time, and Harper’s. He has taught nonfiction writing at the University of Chicago. 

Kirn’s career is remarkable, not only for his ability to move between genres, but for his incisive descriptions, vast literary references, and acid humor, the latter of which he is willing to turn on himself. The Cleveland Plain Dealer, in a review of his 2006 novel, Mission to America, called him “one of the nation’s best satirists.” Someone with such gold-plated credentials might be expected to know his own country. But sensing that something was missing, with the political fires roaring and the pandemic still unimagined, Kirn got into his Jeep Cherokee one morning in February 2018 and took to the road.

Walter Kirn ’83 has written eight books, two of which, Thumbsucker and Up in the Air, have been made into movies.
WALTER WRITES Walter Kirn ’83 has written eight books, two of which, Thumbsucker and Up in the Air, have been made into movies.

Traveling cheaply and subsisting on snack food and soda, Kirn adjusted his path as the mood struck him. After setting off from Las Vegas, he crossed the country’s southern tier, spending long stretches in New Mexico and Mississippi, cutting across Tennessee coal country, and finally reaching the North Carolina coast before returning by way of southern Ohio, Indiana, and Illinois. Unlike some literary road trippers, Kirn neither stuck to the interstates nor avoided them. “The trip,” he insists, “was not about nostalgia or romanticism.” 

Rather than dwell in the big cities, though, Kirn explored Indian reservations, military bases, and hollowed out small towns. There he found a country that was more durable than he had been led to believe but also deeply bruised — by deindustrialization, globalization, the opioid epidemic, a brain drain, and nearly two decades of war. Outside the enclaves of prosperity and education, Kirn learned, American life is pretty tough. 

Moreover, many of the people he knows, works with, and went to school with don’t help. Kirn unloaded on them in a long interview with The Wall Street Journal last November that proclaimed him “Middle America’s Defiant Defender.” It may seem an odd title to bestow on someone with Kirn’s credentials, but he still considers himself a small-town boy and embraces much of their pride and resentment as his own. “I see the American establishment playing the part of bully toward its own people,” Kirn told the Journal, decrying the banks, law firms, think tanks, and tech companies that “extract wealth [and] energy ... from the provinces and then give back contempt as their end of the deal.” 

“It’s kind of wonderful to me that Princeton isn’t perfect. Because it sure looks like it is. And it sure acts like it is a lot of the time. It should delve deeper into itself, but I don’t think it should act embarrassed of itself.”

He has harsh words for the Democrats who, he believes, cloak their empathy with condescension. It is a point that several political scientists have made in less pointed terms and is at least partly borne out by the party’s ongoing struggle to win support from those without a college degree. For those voters, as Kirn sees it, the problem is that many progressive policies “are not couched in language they understand, and too often they’re couched in language that offends them. It’s hard to tell a coal miner who watched his father cough his lungs out that he has privilege.”

If those voters have a chip on their shoulder, Kirn seems to have one, too. “One thing I really noticed about Americans — they don’t like being talked down to, no matter who they are,” he says. “For me, the real tension in the country is between the people who feel condescended to and the people who feel unjustly accused of condescending to them.” 

Unfamiliarity and ignorance run both ways, though. Kirn says he encountered many people in rural America who were convinced, from all they had seen on television and social media, that big cities are war zones of crime and homelessness. He was even more startled to discover how little people knew about their own neighborhoods. To promote conversation while on the road, Kirn made it a point to ask for directions rather than rely on his phone. Often, people couldn’t direct him to places just a few dozen miles from where they lived, and they sometimes resented being asked.

“You walk into a bar in the old Westerns, and everybody looks up and gives you a once over,” he says, recounting the experience. “You walk into a bar nowadays and no one looks up.” 

The pernicious effect of technology, particularly our addiction to our phones, is a theme of much of his recent work, though Kirn himself, an avid tweeter, blogger, and podcast guest, is hardly a technophobe. Still, he is skeptical that surrendering our photos, biometrics, daily movements, and news gathering to the metaverse will be a fair trade. In a similar spirit, Kirn has turned against what he considers the controlling, rule-laden censoriousness that he sees everywhere around him, which is couched in the language of fairness, safety, and tolerance yet often brooks no dissent. 

He delineated his complaints most emphatically in a Substack post last July titled, “The Bullshit.” “Comfort yourself with thoughts that the same fortunes engaged in the building of amusement parks, the production and distribution of TV comedies, and the provision of computing services to the defense and intelligence establishments have allied to protect your family’s health, advance the causes of equity and justice, and safeguard our institutions,” he wrote. “Dismiss as cynical the notion that you, the reader, are not their client, but their product. Your data for their bullshit, that’s the deal.” 

Perhaps not surprisingly, Kirn has burned several bridges with old friends in the media establishment. His former employer, The Atlantic, he says, “manages to outrage me on a regular basis nowadays,” and he has suggested that Harper’s declined to renew his contract after he wrote a column that skewered the left as “scolds and dullards.” (The magazine’s publisher has said that Kirn was let go because he was late turning in his columns.)

All this may also give some perspective to Kirn’s participation on Gutfeld’s show, which he flies to New York to do in person about once a month. Gutfeld!, as it is now called, is late-night television for the red states, and it has quickly soared to No. 1 in the ratings, including among viewers ages 25 to 54. Kirn says he does the show because he and Gutfeld are longtime friends and likens its panel discussions to “tossing a ball around the infield,” though on Gutfeld’s previous talk show, “The One,” at least, his fellow infielders included Eric Trump and the ball consisted of jokes about Georgia’s new restrictive voting law. 

Kirn has become a regular on Greg Gutfeld’s highly-rated late-night TV show on Fox
NIGHT SHIFT Kirn has become a regular on Greg Gutfeld’s highly-rated late-night TV show on Fox.

Journalist Matt Taibbi, who has been doing a current events and culture podcast with Kirn, suggests that Gutfeld! fills the same role for conservatives that The Daily Show filled for progressives during the George W. Bush years. Kirn does the show, Taibbi proposes, because CNN, MSNBC, and other outlets no longer tolerate his brand of heterodoxy. “They’re not welcoming to somebody who might have an ironic take on the news,” he adds. “They’re not invited that into the airspace of mainstream news consumers, so they go on Fox, because that’s where audiences are.” 

Donald Trump was once a target of Kirn’s derision, back in the 1990s when Kirn edited the satirical Spy magazine and Trump was just a narcissistic real estate mogul. Today, although Kirn declines to divulge whom he voted for, he says that Trump’s 2016 victory did not surprise him and that he never took allegations of Russian collusion seriously. While prefacing by saying that there was much he did not approve of, Kirn summarizes the Trump years as “a daily battle between an establishment that was horrified and offended and a guy who felt he wasn’t getting his chance to be president.” When pressed about whether the Jan. 6 insurrection changed this assessment, Kirn retreats. “Ultimately,” he says, “I don’t feel that I’m in the business of moralizing about the American story. I’m in the business of understanding it.” 

Asked to characterize himself politically, Kirn settles on “anti-ideologue,” but “contrarian” seems just as good a fit. If nothing else, Kirn is someone who feels compelled to step outside whenever he gets too comfortable inside. He thinks it would be healthy if others did, too. “I am an America lover,” he insists, “not in the sense that I want to go out and sing our national songs on the street. But we are a much more complicated, intermingled, eccentric, surprising, and mixed-up country than we appreciate.”

Kirn in a small Western town
MIDDLE MAN Kirn has been touted as a champion of “flyover country” and spent much of his time researching his new book in small towns.
Photo: Erik Petersen

Although Kirn’s road trip didn’t reach New Jersey, odysseys often lead the voyager back home again, and in many ways, Kirn’s spiritual home is his alma mater. “No one,” he acknowledges, “has a more complex relationship to Princeton than me.”

Though his public critique of the University has run to book length, it may come as a surprise to learn that, for many years, the author of Lost in the Meritocracy did interviews for the Alumni Schools Committee. And that he hails Wendy Kopp ’89’s Teach for America, that capstone on the resumes of many meritocrats, as an example of the University’s best service to the nation. Kirn wants Princeton to do more to draw students from overlooked places like the central valley of California, rural Montana, or small-town Minnesota, diversifying itself with a broader set of cultural references and values.

The University has never been representative of the country and need not try to be, Kirn says, but it is at its best when it turns outward, applying its tremendous resources to addressing pressing national problems. It is less than at its best when its gaze turns inward. Kirn does not begrudge the University’s recent attempts to correct its history of racism, sexism, and antisemitism, but fears that they often devolve into what he characterizes as “endlessly repetitive mea culpas” that are both self-serving and fruitless. “I just don’t know that self-flagellation ever got anybody to heaven,” he says. 

Listen to Kirn talk about Princeton and he begins to sound like Faulkner wrestling with Mississippi, but what he says about the University might apply to the country, too. “Princeton can do whatever it wants to sanitize, renounce, revise, or rebuke its past, but it can’t get rid of it,” he insists. “Just like our body replaces every cell yet still looks like us, Princeton may replace every cell, but it will still be Princeton. Its attempt to elude that truth seems a little doomed. For all its sins, it has no other identity to jump to.”

No one intellectualizes more than a literary critic on a road trip, as we have been warned. Still, the road is long and there is so much that is unfamiliar.

“It’s kind of wonderful to me that Princeton isn’t perfect,” Kirn suggests. “Because it sure looks like it is. And it sure acts like it is a lot of the time. It should delve deeper into itself, but I don’t think it should act embarrassed of itself. Because in some ways, the institution that is capable of self-consciousness and improvement and regret is the same one.” 

Mark F. Bernstein ’83 is PAW’s senior writer.