The 1960s is so loaded with crucial shifts in American culture—three presidential elections, civil rights marches, campus unrest, the Voting Rights Act, the Vietnam War, The Beatles, the Summer of Love, the moon landing—that it can be tough to get a handle on the decade. The events were so substantial and so interconnected that it’s hard to even find a place to start.

Kevin M. Schultz knows the decade well. He’s a professor at the University of Illinois at Chicago and teaches 20th-century American history and has a deep interest in the 1960s. Schultz said he was reading a magazine article a few years ago that included a sampling of letters from Norman Mailer to William F. Buckley that had recently been made available when he realized that the unique friendship of the radical Mailer and the conservative Buckley would be a great way to take readers through the decade. 

“I was in awe of the intimacy and of the seriousness with which they were engaging with each other, of the obvious friendship they had, of the obvious respect that they shared for each other,” Schultz says. “I thought that this would be a marvelous way to tell the story of the 1960s—through a radical leftist and a radical conservative engaging through the middle even though it didn’t turn out the way either of them expected. This was a way into the intellectual history of the 1960s through these two marvelous, compelling figures. 

In Buckley and Mailer: The Difficult Friendship That Shaped the Sixties, Schultz focuses on the individual stories of the two intellectual and literary giants and the numerous times that they cross paths—sometimes in friendly exchanges and sometimes not. 

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“I love to tell stories in the classroom and in my writing, and the next step is to put them into their broader context so that they give us a broader understanding of the past,” Schultz says. “I had a great time writing this book. It’s filled with these two dynamic figures who just did amazing, incredible, stupid, awful things.”

The book begins with a debate between Buckley and Mailer in September 1962 in Chicago that was marketed as a prize fight—an undercard to Sonny Liston and Floyd Patterson’s boxing match two days later—with sports writers even betting on the outcome. Buckley and Mailer tangled on the Cold War, traditionalism, civil rights and other issues of the day, and they would spend the rest of the decade arguing big issues in TV appearances, dinners together, and in their private correspondence. 

“They find the culture of American life in the post-Cold War world in the 1950s and early 1960s debilitating, fatally flawed, unable to bring about human fulfillment,” Schultz says. “They both criticize mainstream postwar society for being too bureaucratic, too top-heavy, too oriented toward following specific rules. The way Buckley sees out of it is to have the heavy hand of government be removed—to have the regulatory powers and high taxation removed—to allow entrepreneurs to flourish. The way Mailer sees a brighter path is to have the cultural norms change.” 

Buckley and Mailer moves through a series of set-pieces including Buckley and Mailer’s coverage of the 1964 presidential Schultz cover 1election, Buckley’s unlikely run for mayor of New York City in 1965, Truman Capote’s high-society Black and White Ball in 1966 at which Buckley and Mailer nearly came to blows over Vietnam, and—remarkably—Mailer’s unlikely run for mayor of New York City in 1969. As the book goes on, the 1960s as we understand them today begins to come into view as the backdrop of Buckley and Mailer’s stories. 

“When they engaged with each other, they weren’t just advocating one policy over another in the name of partisanship,” Schultz says. “They looked at their engagement with American society as a way to help Americans lead better, more fulfilling lives. They were thinking way beyond single policy points, so it was fun to see thinkers t ake this expansive, philosophical view. That’s a thing I don’t necessarily find in today’s public intellectuals.”

So did Mailer or Buckley win the 1960s? In a sense, Schultz says, both of them did.

“From Mailer’s perspective, you get greater free speech, rejection of authority, and the ‘marms are no longer going around measuring how high a skirt is from somebody’s knees,” Schultz says. “You get a loosening of cultural norms. You start hearing obscenities in movies all the time, and it’s not necessarily provocative by the 1970s. Mailer wins a lot of those cultural freedoms.”

Well beyond the 1960s, Mailer continued speaking out for individual rights. Mailer’s empathetic and harrowing 1979 novel The Executioner’s Song about a death-row inmate became part of the national debate about the death penalty, and he publicly defended Salman Rushdie after the 1989 publication of The Satanic Verses

But “Buckley wins all kinds of economic freedoms,” Schultz says. “It’s the free market that carries the day in the 1970s and with Ronald Reagan in the 1980s. It’s deregulation, which became the catchphrase of the ‘70s. It’s freedom from bureaucracy of the state. Bill Clinton will later say that ‘the era of big government is over,’ and that’s one of the things that Buckley had been calling for since the 1950s.”

Scott Porch is an attorney and contributes to Kirkus Reviews and The Daily Beast. He is writing a book about social upheaval in the 1960s and '70s.