The critic and dramatist Terry Teachout had many friends, so news of his death at age 65 on January 13 spread very quickly. I heard about it that afternoon, shortly after listening to the episode of the podcast Know Your Enemy dealing with the recent death of another prominent writer: Joan Didion. The podcast and Teachout’s death became quickly intertwined in my mind not just because of the coincidence of timing. Didion and Teachout were both exemplars of a kind of literate and skeptical cultural conservatism that with their deaths now seems a preciously rare commodity. The United States in 2022 is awash in conservatives trying to ignite a culture war, but now there aren’t many conservatives engaged in genuine cultural conversation and debate.

Podcast hosts Matthew Sitman and Sam Adler-Bell were joined by Sam Tanenhaus and approached Didion from a particular angle, focusing on her start as a writer for National Review from 1960 to ’66. In the ’50s and ’60s, National Review had a distinguished “back of the book” that published some of the very early works of not just Didion but also Garry Wills, Arlene Croce, John Leonard, Hugh Kenner, and Guy Davenport. These writers were all metropolitan but skeptical of liberalism, which they often saw as sentimental and doctrinaire. They tended to be aristocratic modernists who prized the well-honed, irony-rich sentence. In the later 1960s, under the pressure of the Vietnam War and the rise of a more populist right with Richard Nixon and Ronald Reagan, many of these writers became disenchanted with National Review and either moved left or become more apolitical.

The best of these writers, notably Wills and Didion, undertook a complex self-deconstruction whereby they applied the same acidic skepticism to their own politics as to liberalism. Along the way, they often found a much larger and politically diverse readership in more mainstream publications like The New Yorker, Harper’s Magazine, and The New York Review of Books. But a kind of philosophical, non-political conservatism continued to shape their thinking.

Terry Teachout was a full generation younger than this cohort, but he followed their arc: He got his start with National Review but eventually embraced a more philosophical and nonpolitical strain of conservatism. While he continued to write for National Review and other conservative publications, his work addressed a wider audience and eschewed the liberal-baiting that dominates right-wing political discourse. As The New York Times noted in its obituary, Teachout over time came to prefer “to work in an apolitical register, assessing art and culture on their own terms.” In this way, he was the last of the National Review line of conservative cultural critics that started with Wills and Didion.

Teachout achieved this status by the dint of enormous effort. He was born in Cape Girardeau, Mo., in 1955, the son of a hardware salesman and a secretary. He titled his autobiography City Limits: Memories of a Small-Town Boy and always spoke warmly of the virtues of Midwestern culture, its plainspoken humility, its earnestness and civility. But if he grew up a small-town boy, he didn’t remain one. His hunger for the world of arts and letters proved too great. He read voraciously and then began to write nearly as much. One of the first novelists he championed was his fellow Midwesterner Dawn Powell. John Updike once described Powell as belonging to that cadre of “Midwestern writers” like Willa Cather and Theodore Dreiser “who felt something epic in the national shift from rural to urban, from provincial sequestration to metropolitan liberation.” Teachout was part of that same epic journey from the hinterland to the big city—and he, too, was in pursuit of metropolitan liberation.

Once in the big city, Teachout made precisely this journey toward metropolitan sophistication. National Review, Commentary, The New York Times, and The Wall Street Journal featured his writing about about Frank Sinatra and Glenn Gould, Veronica Geng and Tennessee Williams, Evelyn Waugh and Bret Easton Ellis. The sheer range of his interests was daunting: the high and the low, Bugs Bunny cartoons and Balanchine, Stephen Sondheim and Whit Stillman, as well as, of course, novelists like Cather and Powell.

I first encountered Teachout’s name in the pages of National Review, where he started as a freelance book reviewer in 1981. He was still in his 20s, midway between an intermittent college career, and he wrote reviews of Miles Davis, Dashiell Hammett, and Colette. The expansiveness of his subjects was alone impressive, but his writing also already possessed his characteristic clarity, erudition, and courtliness. He was opinionated without being obnoxious and always ready with a deft quote or an apt allusion. His tastes tended toward older writers at that time out of fashion but deserving of revival, including Evelyn Waugh, Edmund Wilson, Anthony Powell, and A.J. Liebling. The singular quality he liked most in writing was wit and stylishness, which he had a gift for discovering and quoting. After the third or fourth Teachout piece I read, he joined the list of writers whose byline I was always on the hunt for.

Teachout’s conservatism was hard to miss in these pieces. He was an admirer of Whittaker Chambers and believed not just in Chambers’s testimony (where I’m inclined to agree) but also in Chambers’s politics and analysis (to me an absurd position, since Chambers was prone to make outrageous and easily disprovable claims, such as that spies in Washington led to victory of communism in China). He also admired H.L. Mencken’s tart wit and skill at deflating progressive ideas—traits Teachout examined in the biography of Mencken that he dedicated to William F. Buckley Jr. and Joseph Epstein. In Teachout’s rendering of Mencken, he was not just the illustrious sage of Baltimore but also the great voice of the pre–World War II Old Right and helped broke the stranglehold of the genteel tradition to make room for a more robust, naturalistic literature. While Teachout celebrated Mencken’s literary talent, he also did not whitewash Mencken’s anti-Semitism, and in the book was openly critical of Mencken’s beer-hall nihilism. A similar willingness to confront uncomfortable truths can be found in Teachout’s unsparing accounts of the racism faced by the subjects of his other biographies—those of Louis Armstrong and Duke Ellington. It’s not surprising that Teachout ended up as a Never Trump conservative.

But Teachout, whose natural inclination was toward equanimity and collegiality, perhaps never fully confronted the politics of his conservative peers. Unlike Didion and Wills, Teachout never stopped writing for National Review. His review of a biography of Graham Greene ran in the magazine last year—a magazine that is no longer that of the Goldwater or Reagan right but one that that seems to have settled on a position of being anti-anti-Trump. Not only that, but Teachout eschewed a larger reckoning with the question of how Trump took over the GOP so quickly. It would have been a major contribution for a writer of Teachout’s caliber to make an inquiry into how the right had gone haywire, but he never made the effort.

Beyond partisan politics, Teachout remained a cultural conservative in ways that also invited disputation. He criticized victim art and was skeptical of anything that smacked of being too theoretical or experimental. I was always struck by the fact that, while he praised the graphic novels of Chris Ware and Daniel Clowes, he was cold to the work of Jaime and Gilbert Hernandez, whose Love and Rockets series told stories of a queer, working-class Latin American world that was perhaps outside Teachout’s comfort zone. His attempts to promote a more positive reading of middlebrow culture also always seemed a dead end. The pianist Ethan Iverson wrote a lengthy and important critique of Teachout’s Duke Ellington biography, challenging the way it promoted the myth of an undisciplined artist.

Teachout was always game for a good argument, and on social media, particularly Twitter, he was known for his openness to engaging all comers and critics. For him, conservatism signaled a commitment to tradition, to persevering and building on past achievement. It was a conservatism of memory, not of grievance and spite. This conservatism contained within it the possibilities of a political conservatism too. Tradition is all too often the banner for upholding existing hierarchies and resisting change. But for Teachout tradition could also be cosmopolitan. With his death, this strain of conservatism seems not only rare but perhaps even extinct.