Norman Mailer, August 29, 1969. Bob Peterson/The LIFE Images Collection/Getty Images

This month the Library of America is releasing a two-volume collection of selected essays and four books first published during the 1960s by the late Norman Mailer, one of that decade’s most pugnacious provocateurs and a founder of the Village Voice. This was the decade that saw Mailer, who began publishing in the 1940s, at his most politically active. In 1960 he witnessed John F. Kennedy at the Democratic Convention, a moment he captured for Esquire in an essay titled “Superman Comes to the Supermarket.” Some say that the essay — with its personal inflections, novelistic descriptions, and obvious political preferences — helped launch the New Journalism. By 1969, Mailer was running for mayor of New York City on a platform of secession from the State of New York.

In the years between, Mailer wrote his most influential essays and books on politics and the Vietnam War, many of which are included in this collection. Among those included are two columns he wrote for the Village Voice, and The Armies of the Night, Mailer’s personal and historical book-length examination of the October 1967 Vietnam War protest in Washington, D.C., remembered most often as “The March on the Pentagon.” Thousands attended the protest, including Noam Chomsky, Robert Lowell, and Allen Ginsberg, and hundreds were arrested — including Mailer.

It’s hard to categorize The Armies of the Night. Some say Mailer invented a new genre by writing about his personal recollection of the protest in the third person, as well as from a more historical perspective that goes beyond what he experienced firsthand at the event. Often described as a “nonfiction novel,” it went on to win the Pulitzer Prize and a National Book Award.

This year that book turns fifty. Here, J. Michael Lennon, the new collection’s editor and Mailer’s official archivist and biographer, spoke with the Voice about the lasting influence of The Armies of the Night, what Mailer might have made of the Trump administration, and how we should be thinking about Mailer’s notorious misogyny in 2018.

Norman Mailer, August 10, 1968 Mario Geo/Toronto Star via Getty Images

The new collection focuses on Mailer’s writing of the 1960s. Why that decade?

We had a lot of debate at the Library of America about what to include in the reprint. We finally decided that the 1960s was really when Mailer was at this best, when he wrote his greatest books and won his awards.

Was it hard to decide what to include?

The most difficult thing was trying to decide which essays to use, because they aren’t all formal essays. Some were columns in newspapers and magazines, including the Village Voice. We had to pick the [ones from the Voice], because he was one of its co-founders. He put in $10,000, which was a lot of money in the mid Fifties. And he came up with its name. Well, there’s some dispute about that, but he certainly laid claim to it. You know, a tremendous amount of letters came in attacking Mailer when [the Village Voice] first came out, because he was very insulting and high-handed. But when he left, the same people wrote and said, you know, we kind of miss Norman Mailer — he made the Voice into a great counterculture newspaper. And that’s true, he did, but he also pushed it and pushed it, and he pushed it too far, which he admitted later. He said that if he’d stayed [at the Voice] he would’ve ruined it.

Mailer wrote about John F. Kennedy often, starting with “Superman Comes to the Supermarket.” Is it fair to say he was obsessed with him?

Mailer was terrifically energized by Kennedy. In fact, no person outside of his own family was more important than Jack Kennedy. All his life, he was obsessed with not just Kennedy but the fascination surrounding the man. He wrote about it several times, always trying to understand it.

What was the attraction?

He felt that the years before Kennedy were dominated by generals and patrician figures [in the White House]. He had great respect for FDR, but he didn’t think much of Eisenhower. He thought he was dull and boring. The first time Mailer sees Kennedy, it’s just before the Democratic Convention in 1960. Kennedy rides in in a convertible on a beautiful day, and he’s got this tan that makes him look like a ski instructor and flashing white teeth, and there’s a big gathering of gay people across from the hotel, cheering. And for Mailer it just snapped. He thought, here you have two parts of the Democratic Party coming together — the [counterculture] of gays and hipsters and artists, and the old trade unionists. That moment led to the “Superman” essay. Mailer always said that that essay got Kennedy 100,000 votes.

Kennedy won by 100,000 votes.

Well, you know, it was a very tight election. The magazine that the essay appeared in, Esquire, had a circulation of nearly 1 million. Pretty big for that era. Everybody knew about [the essay]. So it was clearly a factor [in the election], but how much, no one can know.

This year marks the fiftieth anniversary of The Armies of the Night, which is often described as a nonfiction novel. What kinds of artistic liberties did Mailer take with it, and what do you see as the book’s greatest legacy?

Mailer could’ve written about [the March] like a New York Times reporter by keeping himself out of [the narrative]. But he was a part of the protest. He went there to get arrested, and he did. So the question became, how does one write about an event and one’s own participation in it at the same time? He used the fictional techniques of the novel — the scenes, the dialogues, the setting. He also decided to use a style that Henry Adams, Gertrude Stein, and Julius Caesar used —writing about one’s self in the third person. America was divided, so he would divide himself, and in that division he would try to find the truth about the country. Personally, I think the book probably turned the tide more than any other written during that period. It changed the country.

Did it change Mailer, too? He ran for mayor the following year.

Right, so he wins the Pulitzer for The Armies of the Night, and he wins the National Book Award, and a big magazine award, too. All of this is happening at just about the same time that LBJ resigns, so Mailer, riding on the fumes of these victories, says, “That’s it, I’m going to run for mayor of New York.” He donated the Pulitzer check to his own campaign. Gloria Steinem agrees to be his treasurer, Allen Ginsberg gets involved, and all of New York’s intellectuals get behind him. He didn’t do very well, but he didn’t come in last — he came in fourth out of five and took it all very seriously. Many people said later that his campaign was really about ideas: The idea of a rail line around New York City, the idea of farmers’ markets in New York, which of course are everywhere now. He had the idea of having one Sunday a month when no one could drive a car in the city. He wanted to make New York City the 51st state. Some of the ideas were crazy, some impossible, but they made people think about community in new ways.

You knew Mailer personally. What might surprise us about him?

Over the course of time, I managed to put my hand on virtually every book in his personal library. [It] includes books about butterflies, beetles, and stones, ancient history, local history. People tend to remember him as a crazy wild man, because the media loved that stuff. But he was actually a very bookish guy.

Was he someone who actually liked to be challenged in public? Or was that all a performance?

He thought that truth comes out of opposition and that when you got into a good debate with someone, the idea wasn’t to win but to encourage each other to ask better questions. And so at dinner parties, cocktail parties, riding in the car with him, there was always a debate. He didn’t do this as a stunt. I think that anyone who reads his work seriously will realize that he was quite a serious thinker and really wanted people to think about deep questions and especially about the fate of the United States as a democratic experiment. He’d be right on point right now with our new president.

Did Mailer know Trump?

Oh, yeah. They weren’t close friends or anything, but they were both part of the same social scene. Trump used to fly his friends down to Atlantic City to casinos and boxing matches. Mailer went down there with Jack Nicholson once in one of Trump’s helicopters.

What would he have made of Trump’s presidency?

There’s no doubt that there are certain things about Trump that Mailer would’ve admired. One of them was the idea that the white lower class has been forgotten. Mailer wrote about them a lot, about how they were being left out. Remember, Norman was always looking for a bridge between the left and right. He was good friends with William F. Buckley and Pat Buchanan. He admired Senator Dole. Ultimately, when push came to shove, he was a man of the Left: He flirted with the Communist Party and supported the progressive candidates in 1948 against Harry Truman. He thought that socialism had a lot to offer, and he was all for social programs. But from the mid Sixties on, he described himself as a Leftist conservative and wanted to be in touch with both sides.

Let’s discuss Mailer in the context of our current post–Harvey Weinstein moment. How should we be thinking about his treatment of women?

[Mailer] came out of the Mad Men era of the Fifties and thought that men needed to be strong and masculine, but [he] was never accused of hurting any women.

He stabbed his wife!

Oh, he stabbed his wife, yeah. He…had a complex relationship with women, and he regretted many of the things he said about them. He knew those things were stupid. But his point of view was, well, “I am doing this to create a debate.” The women’s movement [back then] wasn’t perfect, and Mailer wanted to question [the women involved in it] and have a debate. But there’s no doubt that his views of women writers were twisted, and he only realized later on that he was being very sexist and hadn’t appreciated some great writing by American women.

If he was a man of his time, why should we read his work in 2018?

Because he was a hell of a writer. And because his understanding of the American experience was fantastic. But it was also flawed in many ways. He was outspoken on many occasions when he shouldn’t have been. He wasn’t sympathetic when he should’ve been. He was an imperfect American, but he loved America and wanted the country to survive. He changed the course of prose writing in this country, and no one in the literary world told us more about what was going on in the 1960s politically, socially, and sexually than Mailer.