To National Review readers, John O’Sullivan hardly needs an introduction. He served as this publication’s editor for about a decade beginning in the late 1980s, and he remains a contributing editor as well as a National Review Institute senior fellow.

Conservatives on several other continents know his name just as well. Born in Liverpool, O’Sullivan came to NR off a stint as a special adviser to Margaret Thatcher, and he has since led organizations as far flung as the Australian magazine Quadrant and the Danube Institute, a think tank based in Hungary.

In Sleepwalking into Wokeness: How We Got Here, O’Sullivan collects 41 of his essays, originally published as far back as 1985 and as recently as last year. The topics range from the 2008 recession to the history of the Tory Party, and from Third World immigration to the Me Too movement. The formats vary from book reviews to essays about current events — and the personalities featured stretch from William F. Buckley to the Irish diplomat and writer Conor Cruise O’Brien.

A theme, O’Sullivan notes in his preface, is that “the revolution of ‘Wokeness’ that currently assaults us is not a complete novelty but a fusion of earlier ‘movements’ rooted in similar or related ideological beliefs and often, alas, fallacies.” One doesn’t have to read the collection through that lens; it works just fine as simply an eclectic assortment of essays from one of conservatism’s most perceptive and accomplished thinkers. Nonetheless, it’s rewarding to search for the through lines connecting the political battles of decades past to those of today. And it’s encouraging to remember how yesterday’s conservatives and small-l liberals rose to confront challenges — such as Soviet Communism — far greater than today’s woke obsessions with race and sex.

The connect-the-dots approach to the book comes easiest with the first essay, a July 2020 piece from the Hungarian Review in which O’Sullivan himself explicitly links that summer’s anarchy — which took hold not only in American cities but elsewhere as well — to China’s Cultural Revolution of the mid 1960s. The oppressor–oppressed lines that Maoists drew based on class, the wokesters drew by race. Antifa played the role of the Red Guards. And so on.

Also of particular note for NR’s readers will be a six-essay section entitled “Assessing the Heroic Age of Conservatism” in which O’Sullivan reflects on the legacies of figures such as Ronald Reagan, Thatcher, and of course Buckley — the generation of conservatives who won the Cold War and demonstrated the power of free-market economics. This was a time when the world was consumed by truly monumental challenges, and the Right provided the solutions.

O’Sullivan’s 2013 obituary of the Iron Lady is especially well done, paying tribute to his old boss and her accomplishments while appraising her legacy. In the face of dogged resistance at home, she privatized industries that had been under state control, fought with labor unions, and worked with Reagan to speed the end of the USSR. In the years that followed, her economic successes proved a role model for countries across the globe similarly in need of a free-market jump start.

Today’s conservatives should take heart from this period, which proves not only that the right ideas (pun intended) can save the world but also that history will eventually recognize real accomplishments. In his 2009 review of Steven F. Hayward’s The Age of Reagan, O’Sullivan notes the many travails the 40th president faced, from an assassination attempt to Iran–Contra to an “almost comically biased media.” But it’s easy to forget how embattled Reagan seemed through much of his presidency, O’Sullivan adds, given the more favorable assessments even of liberal historians recently. Similarly, O’Sullivan reports a wide consensus at the time of Thatcher’s death that she was “one of the great figures of British history.”

Yet if conservatives can unite in adulation of Reagan and Thatcher, they are perhaps doomed to bicker forever about the merits of populism and nationalism, topics that recur throughout Sleepwalking into Wokeness. In the European context, these debates often relate to the surrender of sovereignty to international bodies and, in Brexit, a popular urge to take that sovereignty back. (Don’t miss “Goodbye to All That — an Original Eurosceptic Looks Back,” in which O’Sullivan recounts how he opposed British membership in the European Union’s predecessor organization all the way back in the late 1960s and early 1970s.) In the U.S., of course, they generally revolve around Trump nowadays, and O’Sullivan includes here his contribution to the 2017 debate inspired by Ramesh Ponnuru and Rich Lowry’s NR cover piece defending nationalism.

Despite the conservative movement’s many victories in recent decades, it must also be said that the Left won the cultural and sexual wars that most directly presaged the fights over modern wokeness. Particularly stunning here is O’Sullivan’s 2023 piece reviewing The Best of Enemies, a play about the legendary 1968 debate between Buckley and Gore Vidal.

“Vidal sees Buckley as the advocate of a fading American empire that at home is racially unjust, sexually bigoted, devoted to greed, and heading for trouble,” O’Sullivan writes, while “Buckley treats Vidal as someone whose essentially frivolous advocacy of cultural and sexual revolutions — unless it is sharply challenged — will undermine what is essentially a decent civilized country, warts and all.” One is struck that our current debates on these matters could be described exactly the same way . . . and also that, in ways good and ill, the goalposts of “cultural and sexual revolution” have moved immensely since that epic confrontation, which, after all, famously ended with Vidal calling Buckley a “crypto-Nazi” and Buckley losing his temper, responding with a homophobic slur and a threat.

Still, the argument isn’t over, O’Sullivan suggests, as today’s forces of wokeness have provoked immense resistance. And Vidal’s “brave new world of untrammelled sexual libertinism” may have arrived, he adds, but Vidal would not have predicted that “this victory would take place under the management of the same kind of grim doctrinaire puritan academic scolds he disliked even more than he disliked Republicans.” Here, O’Sullivan echoes themes from the book’s Me Too essays, one concerning the declining reputation of Hugh Hefner and the downfall of Harvey Weinstein (both of whom were liberal heroes not so long ago), the other focused on allegations of misconduct against members of the British parliament. A pure sexual free-for-all does not work; without traditional morality and etiquette, we must lean more heavily on formal rules and laws.

If I have any issue with Sleepwalking into Wokeness, it’s a quibble with the title. Many in the West have certainly been blindsided by the far-left ideology that has risen to prominence in the past decade. But reading O’Sullivan’s dispatches from across the globe going back almost 40 years, one sees not a drowsy and uneventful time that lulled the West into a sense of complacency, but a world brimming with highly consequential developments, one where conservative leaders fought valiantly and successfully to bring down communism, improve economies through free-market reforms, and maintain their nations’ sovereignty — and much less successfully confronted threats to traditional morality. It’s a case of being caught off guard and a bit distracted, not asleep at the wheel.

But whatever you call it, read it. Sleepwalking into Wokeness is one of the broadest, most readable, and most insightful essay collections you’re likely to find.