Kevin Simonson of Omaha realizes he occupies an unlikely position as a leading chronicler of that dark jester of American letters, the late Hunter S. Thompson.

Thompson, a New Journalism exponent, gained a Grateful Dead-like following for his irreverent, self-referential Gonzo-style reporting on America’s underbelly. During his lifetime, he was portrayed in film by Bill Murray (Where the Buffalo Roam) and Johnny Depp (Fear and Loathing in Las Vegas). A Doonesbury character was based on him.

He was already a counterculture icon when Simonson, a Wahoo native, got turned onto his work while a Doane College student. The enterprising Simonson and his brother Mark published an underground newspaper, The Great Red Shark, which evolved into The Reader. They booked Thompson to speak at the University of Nebraska, but the author reneged owing to legal troubles with a porno producer (Thompson once managed an X-rated theater). Simonson’s taped interviews with the producer became evidence in legal proceedings that saw felony weapons charges against Thompson dismissed. Leveraging Thompson’s gratitude, Simonson gained access to interview him several times over the years for such national pubs as the Village Voice, Hustler, Penthouse, and Rolling Stone.

“The hardest thing was just getting him to commit. With him, it wasn’t a sit-down interview. It was like, click-on-the-recorder and he’d go crank up some music for a half-hour, to where you couldn’t hear anything. He couldn’t sit still very long. I’d get a few questions in here and there, then he’d take a phone call or go outside and shoot his guns off. It would stretch on for hours.”

Interviewing Thompson could be a real trip.

sDeciphering his low, quiet, gravelly voice—near unintelligible when stoned—required asking Thompson to recreate what he said.

Simonson entered Thompson’s trusted inner circle. Several times he visited the author at his infamous Owl Creek Farm in Aspen, Colorado, a scene of odd characters and goings-on. He ascribes losing his former fiancee to getting her a job as Thompson’s assistant. The assorted weirdness freaked her out, and she and Simonson split.

He was so deeply immersed in Thompson lore, he says, “Anything he talked about, I could talk about. I sort of knew him inside-out. The first time I walked into his house, it was like walking into a museum. I looked around and recognized things from certain books or stories.”

Simonson finally did get Thompson to speak in Lincoln (in the spring of 1990, a month after the original booking date). Typical for Thompson, he ran hours late and took the stage, presumably under the influence. People were variously delighted or outraged.

“I grew up with Spy Magazine, National Lampoon, and Saturday Night Live, and I thought his writing was the funniest stuff ever done. You could turn to any page and there was something laugh-out-loud funny about it. That’s what attracted me to it,” Simonson says.

Thompson, too, represented a refreshing, unfiltered, unapologetic voice and uninhibited, nonconformist lifestyle. “It was his bad- boy attitude and the way he would do things in public and not be even remotely self-conscious about the repercussions,” he says.

Simonson’s widely published work includes authoring and co-editing Conversations with Hunter S. Thompson  He’s helped build the cult of personality around the writer. Even in death, Thompson’s mystique grows larger with every new book and film out on him.

“It’s kind of crazy,” says Simonson, who has also managed bars and done marketing and promotions work for Boston University (during a few years on the East Coast) and KFAB and Clear Channel Radio in Omaha. He was the original managing editor of The Reader, where some of his Thompson work has appeared.

As Thompson’s health declined, he talked suicide, but Simonson and others were surprised when he fatally shot himself in 2005. Simonson was among 250 invited guests at a surreal Owl Creek memorial celebration. In the shadow of a towering Gonzo statue, Thompson’s ashes were shot out of a cannon. Booze ran freely. A film crew captured it all.

When not chasing literary dreams, Simonson manages a golf course in Fremont, where he directs a 5K mud run. He possesses much Thompson memorabilia (taped interviews, faxes, photos, keepsakes). His “most prized possession” is a Fear and Loathing first edition inscribed with a personal note by Thompson and an original caricature by illustrator and frequent Thompson collaborator Ralph Steadman.

Simonson feels fortunate he got close to Thompson and rues his loss.

“I feel really lucky. There’s definitely a void in the literary and even entertainment community with him gone. He definitely made a huge mark on the whole pop culture scene. I miss talking to him. It was always an event when he had a new release out.”

Thompson was not the only late literary giant with whom Simonson was acquainted.

The Simonson brothers, Kevin and Mark, brought literary star Kurt Vonnegut to lecture at the University of Nebraska-Lincoln in 1991. To their surprise, he readily agreed to an interview in a local strip club.

“Compared with Hunter, he [Vonnegut] was like hanging out with Mark Twain. He was funny and so easy to talk to,” Simonson says. His Vonnegut interview ran in the December 2016 issue of Hustler.

Visit facebook.com/conversationswithhuntersthompson to learn more about Simonson’s book. Visit 5kthehardway.com to learn about his (non-literary) work with Nebraska’s Mud Run.

This article was printed in the March/April 2017 edition of Omaha Magazine.