When Dinner Goes Gonzo

If I could have dinner with any author, living or dead, I think I’d choose Hunter S. Thompson.

And honestly, I’m not entirely sure dinner would go the way I imagine it.

Thompson was one of those writers who seemed impossible to separate from the stories he told. He wasn’t exactly the quiet author sitting in the corner with a notebook. He had a personality that was almost as famous as his writing.

That’s part of why I’d want to have dinner with him.

I’d want to know what it was like inside his head.

I’d definitely want to talk about his writing, but especially the infamous Gonzo journalism he became known for. I’ve always found the idea of Gonzo fascinating because it blurred the line between the journalist and the story itself. Instead of simply observing what was happening, Thompson became part of it.

I actually had a little experience with Gonzo journalism myself in college. We were asked to create a magazine, and I chose Gonzo journalism as my inspiration. It ended up being ranked in the top 25 in the class.

The magazine cover I created is also the featured photo for this post, which feels fitting considering where my interest in Gonzo journalism began.

I’d want to know how Thompson came up with that approach.

Did he always know he was creating something completely different, or did it develop naturally as he wrote? What made him decide that inserting himself into the story was the best way to tell it? And how much of what we read was carefully planned versus simply following wherever the experience took him?

I’d probably have a million questions.

I’d also want to know about the stories behind the stories. What was happening when he was writing them? What did he leave out? Were there moments when even he thought, This is completely ridiculous?

Because I imagine dinner with Hunter S. Thompson would be anything but boring.

I’d want to hear the strange stories. The funny ones. The ones that probably started with, “You’re never going to believe what happened…”

But I don’t think I’d want the entire dinner to be an interview.

I’d want to hear the stories that came up naturally.

I’d want to know what he thought about when he wasn’t writing. What made him laugh. What irritated him. What he believed. What changed his mind over the years.

Writers spend so much time turning life into words that I sometimes wonder what they think about when the notebook is closed.

What did he notice that other people didn’t?

What did he see differently?

And what made him want to keep writing when he knew his approach was so unconventional?

Maybe that’s what I’d really be curious about.

Not just the famous Hunter S. Thompson everyone knows, but the person underneath all of it.

There’s something fascinating about the idea of sitting across from someone whose work has stayed with you and realizing that, underneath the books and the reputation, they’re still just a person. Someone with stories, opinions, memories, contradictions, and probably a few things they never told anyone.

I think that’s what I’d really want from that dinner.

Not just to meet the author.

To meet the person behind the words.

And if the conversation happened to become completely unpredictable along the way, I’d probably be okay with that.

After all, if you’re having dinner with Hunter S. Thompson, I’m not sure you should expect anything else.

Featured photo: The Gonzo-inspired magazine I created in college, which was ranked in the top 25 in the class.

If you could have dinner with any author, living or dead, who would you choose—and what would you want to ask them?

“Buy the ticket, take the ride.”— Hunter S. Thompson