A literature professor explains what everyone gets wrong about Hunter S. Thompson

It's easy to appreciate Hunter S. Thompson first and foremost for his style, for that famous Gonzo prose knocked off so often (and often so poorly) it's almost startling to revisit his work and realize how clear-eyed and articulate both his fear and loathing always were on the page. In Timothy Denevi's new biography, Freak Kingdom: Hunter S. Thompson's Ten-Year Crusade Against American Fascism," fear and loathing receive a re-appraisal as the rhetorical framework that Thompson employed deliberately and with very specific ends in mind while creating some of the most influential journalism of the 1960s and '70s.

Through meticulous research and recreated in novelistic detail, Denevi chronicles Thompson's scramble to create a viable career out of the instability of freelance writing throughout the formative decade of his work, beginning with John F. Kennedy's assassination and ending with Richard Nixon — the primary enemy Thompson focuses on during this time — departing the White House in shame.

If you've ever felt Thompson a bit much to read on his own, "Freak Kingdom" makes a handy and stabilizing companion text: the behind-the-scenes details of how his big stories came together make it impossible to dismiss Thompson as the pop culture caricature he was later made out to be, a party monster who somehow managed to stumble high and drunk through covering epic American episodes and themes: the 1968 Democratic National Convention, the rise of the Hells Angels and the hell of Las Vegas, the horror of Nixon's presidency.

"Freak Kingdom" doesn't shy away from the messier sides of Thompson's life — his alcoholism, for starters, and the Dexedrine he took in attempts to counteract it while he worked — but Denevi contextualizes Thompson's outsize persona within his professional enterprise, namely the targeted vigilance against the rise of authoritarianism and the threat of state-sanctioned violence that animated the urgency of his work.

I sat down with Denevi in Thompson's home town of Louisville, Kentucky, this week, to talk about the many ways the past isn't even the past and how Thompson's work and life have been misunderstood.

So you worked nocturnally, like Hunter Thompson often did, to finish the book?

To be able to engage the subject I wanted to write about, it was very difficult to also exist within modern America. Not just within our email systems, our jobs, but also within our media environment. The Las Vegas shooting [last year], if you’re online when that happens and you’re trying to write about America, and this new horrific development about America comes out, it’s very difficult to articulate a perspective. So instead, being able to stay up and work at night, to not have emails to respond to, and being able to not have New York Times alerts — oh my god, they’re never good, if they’re neutral that’s the best — to not have that was very important, to be able to engage a time period in American history, 50 years ago.

1968 was a fucking terrible year. It was one of the worst years we can ever imagine. Martin Luther King Jr. was killed. There were riots about the anger over having a modern prophet murdered for his [search for] justice. Then two months later Bobby Kennedy, the only candidate articulating what America might be, was murdered. And in Chicago [at the Democratic National Convention] everybody was, as journalists, and as political officials, violently beaten. Then Nixon won after all of that. It was ridiculous. [But] to take all of the emotion of the present and throw it at the past, and deal with how hard it was then, was easier than dealing with how hard it is now.

And yet as I read the book it was impossible for me not to think about our current situation —the president’s relationship to the press, to the truth, about his and his circle’s potential to be ruthless and to do whatever they need to do to win. I can’t believe we haven’t progressed further, especially with how Nixon’s presidency ended.

We thought it would be better. We drove him from the kingdom. We took an evil king and sent him away, as a democracy. And it didn’t get better. It’s so sad. That’s why [George] McGovern winning instead would have been better than Nixon being impeached. That’s why defeating Trump in two years — he deserves to be impeached, from the moment he woke up he deserves to be impeached, he’s an unjust, crooked, completely unapologetically corrupt person. Nixon deserved to be impeached. But it didn’t make America better, and that’s terrifying.

It’s going to get worse before it gets better.

Hunter Thompson has gone from having a reputation as a sort of disreputable outlaw-writer figure whose debauchery was celebrated, to being treated more as a serious literary figure as the generation he influenced has come of age. We’ve seen his legacy change over time as people take his work more seriously, but perceptions die hard. What’s the thing that people get the most wrong about Thompson?

I think most people forget that Hunter S. Thompson started as a professional journalist who had to write what was asked of him at every single point. We imagine, perhaps, 50 years later in the present, choosing to start where Hunter S. Thompson ended up. So you write something memoiristically, or you go to a concert and you write about how you felt at the concert, or you go to a political event and you write about how you felt at the political event. We misjudge him. We think he began there.

But he spent so many years within the journalistic world as a freelancer playing by their rules, doing what they asked him to do to make money for his family, to be a better writer, and to comment on America. And finally he was able to work his way high enough through the freelance world that he could then stylistically articulate how he saw America more directly in that way we identify with him.

I think a lot of people tend to imagine he began there, writing in the way that he did. But instead he wrote what he was asked to, and then after doing that for so many years, he was able to deviate from that journalistic norm and create a voice that was his own and was beautiful — as Joan Didion did, as James Baldwin did beautifully, as so many of the New Journalists did.

That foundation and training of straight journalism is the part maybe novices who idolize him want to skip over because his voice, in his prime, feels so natural to us now. One thing I appreciate about your book is the nuts-and-bolts approach to describing the work behind how he put these iconic stories together, too. The process of it, I feel, is often overshadowed by the personality.

For people who have never heard about Hunter Thompson except through the excess personality, or for people who know his writing and love it, I’d like this book to be an opportunity to see our present through his incredible perspective in the past.

His ongoing concern with fascism across the ten years depicted in the book, and how that formed a throughline in his work, I think that’s not an easy thing for people to see on the surface. You can be aware of his individual great works but not necessarily see that the thing that ignited his interest in the Hells Angels before anybody knew anything about them, and the District Attorneys conference in Las Vegas, and the campaign trail — American fascism always bubbled beneath the surface of the things that held his fascination.

American fascism is violence, and it’s American violence, and it’s violence we’ve had since the beginning of our democracy. Thompson looked at America, especially in this ten-year time period, and he saw people enforcing their undemocratic points of view with violence, whether they were Mayor Daley, whether they were very angry Hells Angels, whether they were a masculine group of unjust rage, or state-sanctioned violence like the Los Angeles Police Department, he saw their violence and he saw their injustice intertwined at that fascistic point.

I read in Umberto Eco’s “Ur-fascism,” writing as an Italian who grew up in the 1930s during fascism, that fascism is messy totalitarianism, which is why it’s so dangerous to America. It’s the step that you cross over to, where suddenly what was going wrong in democracy becomes state-sanctioned authoritarian violence. And we’ve crossed that step a lot of times in American history, and we’re at that point again. Eco gives his list of 14 features of fascism. And for him to say it’s messy, it has no ideology, that it’s about the cult of the central figure, it’s about speaking for the group instead of the people who are victimized by the group, to read that and to look back at what Thompson was writing about and to see the word “fascism” repeated in his writing. When he says the central bent of the Hells Angels — and I’m misquoting it — was fascistic; they were violent men who didn’t want to reason with you, they wanted to abuse anyone who had less power. That’s a very American trait. We see it right now. It’s happening, sadly and ridiculously, over and over again. To look back and hear him articulating it was, for me, terrifying but also invigorating.

I was surprised to learn about the real genesis of “Fear and Loathing in Las Vegas.” That was my entry point to Thompson’s work, as I think it was for a lot of readers. To read that the story actually began with an earlier trip with Oscar Zeta Acosta, and to understand how the book ultimately affected their relationship, and how fraught that became especially as Thompson’s profile rose and Acosta’s sank, and how their friendship ended —

[Thompson] signing that letter “Whitey”, yeah.

“The Rise and Fall of the Brown Buffalo" is such a beautiful documentary. Phillip Rodriguez is so amazing on his perspective on white supremacy, American democracy, and the 1960s and '70s. That film is a gift. I was so happy to have been in touch with [Rodriguez] and Ricardo Lopez, a producer, who’s also amazing. He had done FOIA requests for the last 30 years about Oscar Zeta Acosta. And realizing how much the FBI, how much the Los Angeles Police Department, were seeking him out and trying to destroy him, it goes back to the question about Thompson and Acosta and what I think we miss about the 1960s: the goal of law enforcement at certain times was to infiltrate a legitimate civil rights organization, have undercover agents then attack police while pretending to be part of the civil rights movement, and then police could use lethal force which is the most terrifying weapon the American republic has to silence dissent. That was happening with the Black Panthers, it happened with the Brown Berets, it happened obviously all throughout the 1960s.

We know that, but to see it — and this is why I think it’s important for [understanding] Thompson — Hunter Thompson really believed as a white man who didn’t go to Harvard that he was outside of the mainstream. He deeply believed that, and he was wrong. But he met Oscar Zeta Acosta, who said [to him], I have been working my whole life to make this world better, I have done everything I possibly can, we live in an unjust system that will destroy me through my effort. Thompson really wanted to continue to work within the American system to make things better, and Acosta eventually looked at him and said, there is no amount of effort I could put out that would allow me to make this better, because it’s rigged from the start.

The tension between Thompson’s idea of how to work within the system and Acosta’s idea on how to work with the American system fueled both of their works brilliantly.

I was surprised to learn in your book that the two initially went to Vegas not to party, but to be able to have a conversation without surveillance so they could get to the heart of how Thompson was to understand the murder of journalist Ruben Salazar.

Ruben Salazar was a brilliant journalist, and he had his head blown off [by a tear gas canister fired into] the Silver Dollar Café by a police officer who knew what he was doing. When Thompson came in to write about it, Thompson really wanted to get to the bottom of the story and to articulate how the Los Angeles Police Department and how the Los Angeles Sheriff’s Department had abused and completely disregarded our sense of justice.

But the Chicano Rights movement, the Brown Power movement, it was so attacked and infiltrated by the Los Angeles police that Thompson, who we can both imagine did not look like a cop or act like a cop, when he came into LA for those two weeks in March of 1971, was deeply distrusted. So for those two to get into the car together, to have the top down, for them to both finally say, I know at this moment nobody is listening — and in retrospect they were being observed, Acosta had been completely bugged — for them to be in the car together and for Thompson to be able to say, just explain to me why it’s so awful, what went down, and to have nobody around them judging that conversation, was amazing. Of all the moments we’ve missed in this world I would love to have heard that conversation of those two in that car driving together in the desert, with the wind as a translucent barrier so they could allow themselves to be more intimate in their talk.

Another throughline in the book I appreciated was how clearly Thompson carried grudges with him from the 1968 Democratic National Convention in Chicago; not just the police violence outside, but also what happened inside on the floor. I feel like Americans are so good at not teaching history, not learning history, and forgetting it almost as soon as it happens or distilling it down to the most convenient image or soundbite we can get our hands around, like the image of the protester flipping off the police being the one that endures from the ’68 riots, not the police brutally beating civilians and journalists and campaign staffers.

Americans want that to be the only aspect of it: Both sides are wrong! He was youthful.

Power is deeply entrenched. Justice is practiced. It’s not ever an ideology that works. What we learned from the 20th century is ideologies will always fail us. Especially with the Democrats and Republicans of the 20th century. Lyndon Johnson saying he was going to try to enact Civil Rights reform and try to make this world better, and also your children are dying and I’m not going to do anything about it, I’m going to lie to you about why the war is occurring and I’m never going to admit how much I’ve disseminated in regards to Vietnam. It was terrifying.

It's troubling seeing how hard the cult of personality is at work now — right wing politicians are going even further right and they’re being loved for it. To think how much of what's wrong with the country today has been propped up by people who were young during the ‘60s, who did see their friends and classmates killed, who knew what Nixon and Johnson did, it strikes me that maybe it made an entire generation both extremely cynical about power but also willing to accept any abuse of it. The paradox of it to me is how in the long run that generation didn't become even more idealistic in response.

The Baby Boomers somehow moved through understanding abuses of power and also learned how to use power abusively when they got older.

The way we were divided in the 1960s was often generational. To have that divide again, with the Baby Boomers who were the teenagers then on the other side saying America is under threat, being invaded, at risk, and having brilliant, young millennials and the generation coming after them articulating back to their parents and grandparents that everything that’s happening now, you don’t believe in, and then to have Boomers reply back, essentially, I don’t care if I don’t believe in it, it’s what I’m going to support, is so maddening and terrifying.

The idea that there’s nothing left to believe in, I don’t know how to understand it except as a generation’s untreated trauma.

I think it’s also about the generation coming close to the horizon. The Baby Boomers were the most educated and socially just that had ever existed, in their post-war world, they had all the opportunityand ability to understand what is just, and many of them as young individuals articulated that. And to see them now at the end of their orbit pulling down the rest of the world through global warming, through politics, it’s inexplicable. You’re talking about migrant workers stealing your jobs? You know that’s not true.

Then again it’s entirely possible that so many white men weren't looking for justice, even within the counterculture, they were just jockeying for their own positions of power within it. I think about the scene in your book that describes Thompson witnessing what reads like a gang rape [at a Merry Prankster acid party with the Hells Angels] and for him to reflect that horror, instead of depicting it as a free-love good time, shows that he had a moral compass that guided his work strongly. Do you feel that when people talk about his writing that gets buried under the lifestyle, the drugs and such?

Hunter Thompson is really good at trying to see what’s necessary and not, in terms of justice. When you abuse and you rape and you’re violent as a culture, he knew that was terrible, and he had a sense of, in terms of articulation that Norman Mailer didn’t have, to say I am viscerally disgusted by how this white male bro culture, which was Stanford in the ‘60s, was acting.

What helped me in writing this book was Joan Didion, knowing she was the best and most successful at these major publications. For her to be in that position and the amount of effort she had to put out, to be able to not be a white male writer doing that, and to see her perspective which is so minimalist and brilliant, helped me understand what was going on then.

How would Joan Didion write about that scene at the party? Differently. She would have seen it in terms of justice. Mailer wouldn’t have seen it in terms of justice. He was good at the broad concept of America, but he wasn’t good when it came to writing the moment he was in. He watched Nixon step off the plane in Miami in 1968, and he writes about the Nixonettes, and he rates them. Come on, this was bad at the time. It was unjust then.

Hunter S. Thompson wrote about white men in power. He didn’t write about gender, he didn’t write about — except when he had a purchase — race. I think he knew his limitations in terms of justice, which is what drove a lot of his art to begin with. That’s something that holds up, whereas Mailer doesn’t hold up in the same way.

Speaking of gender, Jessica Hopper wrote this amazing oral history for Vanity Fair about the women editors at Rolling Stone in the copy department who professionalized the magazine, taking raw work from mostly male journalists and transforming it into what we now know as these legendary stories. Just like Hunter’s first book editor, Margaret Harrell, they all had these amazing educational pedigrees and they showed up to work and they were told they could be secretaries, and they fought their way into creating a copy department and turned Rolling Stone into a legitimate journalism publication. Thompson was just one of the marquee men there whose work depended on the unheralded and underpaid labor of women.

From the late 1950s until the end of his life. Margaret Harrell, who is brilliant and who I was able to talk with for the book, is so amazing. I think it’s fascinating that, when Hunter Thompson interacted with her over the phone at first, as a sexist assumption he thought she was a woman in her fifties, who, because she was very talented, knew exactly what was going on. And she didn’t correct him for months. [Harrell was in fact 26; when Thompson learned that, he felt a "sudden, general electricity."]

That’s self-preservation, so men will take you seriously.

Exactly, so you’ll be able to put those calls through, so you can get the work that needs to be done.

Do you feel like Thompson’s moral compass, his intolerance for injustice, gets overshadowed by this reputation he got for being a sort of nihilistic character, because Americans still think of alcoholism, of drug use and abuse, in moral terms? And can you walk us through why Thompson began using Dexedrine to fuel his writing, how that interacted with his alcoholism, and when things shifted out of balance for him?

The horror of modern American society is even though we’re in the 21st century, even though we have all of this information, we still see illness in a moral light. And we see addiction or depression as a moral failure. And that’s never gone away. It’s gotten stronger. Why can you not be somebody who sees right from wrong and what’s necessary and what’s not and also be an alcoholic? He’d been an alcoholic since age 14. Shouldn’t we know as a society that’s separate from your moral development? And instead I think in the 80s, 90s and last decade we’ve run into a very church-like judgment of people who are not allowed complexity. Thompson was racing himself, he was chasing the time he thought he had left.

Juan Thompson’s beautiful book “Stories I Tell Myself” articulates this beautifully, that Hunter Thompson knew since he was 14 or 15 that he was an alcoholic and he chose not to stop drinking or change his rhythms or make amends in terms of how that alcoholism terribly affected his life. Instead when he was very young, in 1964, when he was in his 20s, he chose to mitigate the effects of the alcoholism through Dexedrine, which is very similar to Adderall. It’s a little more up and down, but in the end it’s a way to not be hungover, to not be stumbling, to not be disadvantaged by the drinking you’re doing, as opposed to not drinking as much. I think he knew that with that Faustian wager he made perhaps he’d burn brightly and then be gone. That’s why I ended the book in ’74. But I love Juan Thompson’s writing on the price he paid, because that has to be part of the conversation.

From the start, I think he made that wager that he wasn’t going to change the way he was and the way he functioned, instead he was going to give everything he could for that small period of time. That’s not romantic.

And it’s a story about class also. He had this time period he had to capitalize on, because he was broke. He didn’t have the safety net the Harvard guys had. There’s a version of this story starring a guy from a different kind of family, with a different background, who comes from money and has a safety net and drinks a lot and —

It’s George fucking Plimpton!

Right, and the deal Thompson made was in some ways about knowing he had a finite amount of time to get to the level he needed to get to, so he could achieve some economic stability, and make a living, so he wouldn’t get evicted, so he could pay the bills. And that seems to have been really under-examined in his life.

Freelance journalists are in the same place today. I was panicking just reading about his financial situation.

I think readers might assume his life was all "charge it to the room" which the magazines paid for, and it creates a different picture that wasn’t quite real. Understanding the real story behind his motivation to break big, the very real economic precarity — not to mention his sense of justice being shaped by his class, as it was — explains how class was one thing that led him to push himself physically, too.

If he had been a rich Louisvillian, if he had been one of the judges’ sons in this town, he never would have seen injustice or lived with that constant anxiety about money as he did.

In Thompson’s contract, all of his expenses on the 1972 campaign trail were to come out of his book profits. At the time, he was like, ah fuck it, whatever the future’s going to be will be, he drinks and drinks and goes and goes. But all of that came out of his end. Journalists were treated even then as American workers always have been: without value.

Just one more parallel in this book between now and then, and how things don’t change. So why haven’t Americans in power learned from our violent and nauseating brushes and clashes with fascism in the past?

I don’t think we’ve lost what we have in the way that other citizens of the world have lost. I think their post-war narrative has been one of ideological violence or fighting. Our government continues to represent the people with the most power, and the people with the most power haven’t yet lost what they think they’re wagering the way the people with the least power always are, without even choosing to wager it. When America goes through the hardships that are coming, and I think the political violence and social violence that’s coming, the instability that America is, and I hope not, but is most likely to have over the next 30 years, I don’t know if we’ll learn then.