I was barely 20 and when I first met Harlan Ellison in the too brightly lit cafeteria of South Mountain Community College in Phoenix, Arizona. I had driven with a posse of fellow booksellers to see the infamous SF legend speak at the college, and after what can only be described as Ellison doing stand-up comedy, I made him sign my copy of Troublemakers, got my picture taken with him and then arrogantly told him to remember me. He responded, “Sure kid.”

And more than a decade later, I’m happy to report Harlan Ellison still calls me “kid,” and is just as charmingly outrageous as ever.

Last week, over the phone, Harlan and I discussed the recent re-release of his very first 1958 novel Web of the City, now being reissued by publisher Hard Case Crime. But truly, any discussion with Harlan Ellison won’t be limited to the boundaries of one subject. Most interviews I’ve conducted with authors are a kind of sound-byte piracy: I swoop in and scoop out from their brains exactly what I need to create the perfect piece.

But chatting with Harlan Ellison isn’t like that! It’s the most fun you’re going to have in an interview, but it’s not really an interview. It’s a shoot-out at the O.K. Corral. Sure, these bullets might be rubber, but you’re definitely not just going to get what you think you want. You’re going to have to earn it.

“You’re three days late!” Ellison growled after I introduced myself. This is unfortunately true, and possibly my fault. I decided to remind him that not only did we meet over ten years ago, but also that we spoke on the phone in 2011. That time I talked with Harlan Ellison he thanked me for an article I’d written on Tor.com about a short story of his called “How Interesting: A Tiny Man.”

Luckily he remembered this and said, “Well, I try to be punctilious in these matters,” and then laughed like a jolly gargoyle.

Web of the City, Ellison’s first novel, is in essence a snapshot of gang violence on the streets of New York City, capturing a time and circumstances—an entire universe—which doesn’t exist anymore. The novel concerns the machinations of Rusty as he attempts to leave a gang called the Cougars, who will surely kill him for this transgression. Ellison based much of the character of Rusty and the events of the book on his own experiences in being in a Brooklyn-based street gang at a young age. But just how much of the book is really Harlan Ellison? A lot!

“A lot of Rusty’s background parallels my background on the road as a kid, because I was off on my own very young, age 13. A lot of the scrambling and the shoe leather is autobiographical. The rest of it is just straight action adventure.”

But the New York City of Rusty is not the New York City of now. Having lived in New York City for almost a decade myself, I tried to figure out just how much of Harlan Ellison’s New York and the New York of Web of the City has changed. Ellison tells it like this:

“It’s a very different city now than it was then. And I haven’t been back since before 9/11. But that may be a lie…I remember my city, my New York very clearly. I can walk those streets, but all those people are gone and one by one all the places I went are gone.”

In the introduction to this new edition of Web of the City, Ellison writes of a possible legend about Ernest Hemingway intentionally destroying his first novel. From the introduction:

Yes, the story goes, Hemingway had written a book before The Sun Also Rises, and there he was aboard a ship, steaming either here or there; and he was at the rail, leaning over, thinking, and then he took the boxed manuscript of the book…and threw it into the ocean. Apparently on the theory that no one should ever read a writer’s first novel.

And yet, here we have a reissue of Harlan Ellison’s first novel! I demanded to know from Ellison if we younger writers should all be throwing our first novels into the ocean. As with most of the questions I presented him, his first response was a peal of laughter followed by an amused response:

“The question is an acerbic one…I read so little these days…things coming out are of so little interest to me…that I’m the last savant in the line to ask this question whether their work should be shitcanned.”

This part of the conversation segued into asking what Ellison watches on TV these days. “The test pattern,” he quipped, referring to the bars of color that appeared on CRT televisions, allowing you to adjust your set to its optimal settings. I assured him I was 31, and able to remember such things, but Ellison was nevertheless suspicious and fired back with, “31? I have software older than that!”

One of my favorite anecdotes about Harlan Ellison is the fact that he supposedly wrote his short story “Pretty Maggie Moneyeyes” completely in the nude and that he frequently wrote naked. So I wanted to know, what’s the deal with Harlan Ellison writing naked? He chuckled mischievously before saying this:

“Well it has been fairly recurrent. I wear whatever it is I’m wearing, when I get the urge to write, so if I get out of bed at two in the morning and wanna write I haven’t got the time or the patience to throw on pajamas…but in Vegas when I wrote that story, I did write it naked…God knows why. But that’s like asking ‘why did you put on shoes this morning.’ What is, is.”

Returning to the more serious matter of Web of the City’s relentless violence, I couldn’t help but feel a connection between these switchblade-wielding gang members and some of the other more malevolent forces in Ellison’s SF stories, specifically the sadistic computer from “I Have No Mouth and I Must Scream.” In that story, humans are tortured endlessly by something they once programmed, but I wondered, are we as a species able to escape our cycle of violence? From street gangs of the past to killer artificial intelligence of the future, where does it end?

“We are a very strange species. On the one hand we have Picasso’s paintings, on the other we have the AK-47. And some people are literarily drawn to the physical art of weaponry. If you take a knife, a knife can carve meat, it can carve a whistle for a child, it can be used for sculpting, or it’s a murder implement. A gun can’t do anything but kill!…I don’t know if we can ever escape this. I mean, we’re a fairly young species, but we don’t show a lot of promise.”

To this, I asked Ellison if it was possible that fiction like his own might shine a light in the darkness and maybe, just possibly, help make humanity more aware of the violence it commits. He laughed again before responding:

“You must have mistaken me somewhere for someone who has some knowledge! It is hard to go through life as I have, being a guy who thinks we’ve had a good chance at it and we should turn it over to the cockroaches…BUT every once and awhile there is a ray of light. Every once and while there is an actor, or an artist or a philosopher who says or does something that makes a tiny difference. And for me now, at an upstanding age, I’m no longer the buccaneer, I have to be a little more philosophical…I cannot give you an answer. I’m not that wise!”

While the author’s relative wisdom still up for debate, Harlan Ellison is at least famous enough to be considered on wider platforms. The week before our interview Harlan Ellison recorded a guest spot on The Simpsons.

“I finally made my appearance on The Simpsons. They’d written a Harlan Ellison part for Harlan Ellison. And apart from taking a tumble out of chair in the writers room…it was great fun. And everyone said ‘YOU’RE FAMOUS NOW!’”

But Ellison has always been famous to me and one of my favorite old-school stunts of his was the writing of new short stories in public. Whether in bookshop windows, on the floors of conventions, in art galleries or outside, Harlan Ellison used to frequently sit around and create stories in the interests of reminding people that writing is a real job and quite hard work. I asked him a little bit about his feelings of doing this public writing and what he felt like it meant to people.

“It’s a dog and pony trick…I work well under pressure and most people don’t. Most people look at writing not as a holy chore, but something beyond means. Most other people think it appears magically. A kid came up to me sitting in public [writing on a typewriter] at an art show…and he looked at me punching away on the typewriter and said to his mother ‘What is that thing?’ And she said ‘That’s a typewriter,’ but he couldn’t figure out what it was. So I said ‘It’s magic! I think into it and what I want comes out!’ And he screamed ‘Mommy, mommy, you gotta get me one!’”

This, to me, couldn’t be a greater representation of the dark magic that is Harlan Ellison; lying to a child about the magic of a typewriter, while somehow also telling the child the truth. Even though he might misdirect you with faux-pomposity or a seemingly cynical view of the failure of the human race, he’s actually a laughing chuckling wizard with more in common with Socrates than he lets on. Harlan Ellison’s work is there to make us talk about it and Harlan Ellison is here, maybe even unwittingly, as an example of those rare artists who occasionally make a difference.

Underneath all the humorous bluster, Harlan Ellison loves you, whether you like it or not. Because as I got off the phone with Harlan, the last thing he said to me was: “keep it up, kid.”

This interview took place over the phone on April 15th 2013 and was made possible by Hard Case Crime. Check out Web of the City on Hard Case Crime’s website.

Visit Harlan Ellison here.

Ryan Britt is a long time contributor to Tor.com.