Anyone with school-age children over the last two decades, plus a good percentage of today’s young adults, probably know about “Diary of a Wimpy Kid.” They very likely have copies of the original, or some of the other volumes in the series, on their bookshelf.

Author Jeff Kinney, 50, oversees the franchise that grew from an online hit to a publishing juggernaut that, starting in 2007, took up permanent residence on the New York Times children’s series bestseller list. His wimpy protagonist, Greg Heffley, has been joined by best friend Rowley Jefferson in the publishing ranks, and the latter’s third title, “Rowley Jefferson’s Awesome Friendly Spooky Stories,” will bring Kinney to Colorado in a little more than a week with a traveling, drive-thru event.

* 6:30 p.m. March 15 at Denver BookBar
* 6:30 p.m. March 16 at Tattered Cover at Aspen Grove
* 6:30 p.m. March 17 at Boulder Book Store in Boulder
* 6:30 p.m. March 18 at Barnes and Noble in Fort Collins

The 15th installment in the Wimpy Kid series came out last year to immediate acclaim, and the series already has inspired four films, with a musical theater production in the works as well as a partnership with Disney+.

From his home in Plainville, Massachusetts, where he also opened the book store called An Unlikely Story, Kinney took time to talk to SunLit about his own unlikely story about creating a wildly popular children’s series when his first love, cartoons, didn’t work out.

The following interview has been edited for length and clarity.

SunLit: For the parents out there, and parents to be, who perhaps haven’t heard about your books, tell us what the Wimpy Kid stories are about.

Jeff Kinney: “Diary of a Wimpy Kid” follows the trials and tribulations of a seventh grade weakling named Greg Heffley, who is a little bit too sure of himself. He’s quite certain that he’s going to grow up to be rich and famous despite having any shred of talent that’s evident. And most of the comedy of the books comes from his failings in his certainty in himself. And the books are heavily illustrated. 

They are a little bit different from regular illustrated chapter books in that the DNA of the books is in comics. When I was in college, my dream was to become a newspaper cartoonist like my heroes, Charles Schulz and Bill Watterson and Gary Larson. Right when I got out of college, I found out that nobody was rolling out the red carpet for me. None of the syndicates liked my work and so for about three years, I got nothing but rejection letters. And then after that I decided to chart a new path and came up with this concept and worked on it for eight years before I showed it to anyone.

SunLit: What was the thought process that took you from cartoons to creating kids’ literature?

Kinney: I wish it was a thought process. It was more like failure and rejection. By the way, I love newspapers. I grew up on the Washington Post, and a few others. In fact, I worked at two newspapers, my first two jobs. But you know, I just couldn’t break in. So I had to figure out something else. 

At the time, I was keeping a journal as an adult. And my journals were text laced with cartoon illustrations or pictures of what was going on in my day. And I looked at that, and I said, “Wow, maybe this format could actually work. And maybe if I fictionalized this, it might have appeal.” But I didn’t have high hopes for it. I just didn’t think that it would get published. But I needed something to do. I needed a place to channel my creative energy. 

SunLit: When did you start jotting down ideas for a children’s book? What were you trying to tap into with young readers?

Kinney: You know, people never really believe me when I say this, but all the years that I worked on it, I never thought that I was writing for kids. I was writing for adults who like comics. At the time, the humor section was a really big, important section of the bookstore. And there was everything from books by Seinfeld, to collections of newspaper comic strips, like Calvin and Hobbes. There was a wide range of books in the humor section.

And I thought that I’d write one book that was “a year in the life.” A school year in the life of a kid. And I thought my audience would be people who like comics or people who like movies and television shows like “The Wonder Years,” which were nostalgic, looking back on childhood from an adult’s perspective.

SunLit: When did it dawn on you that maybe you were writing for adults, but kids would just eat this up?

Kinney: That was my publisher’s decision. I brought it to an editor, who brought it back to the pub board. And they collectively decided to tell me that I’d actually written a children’s book, which was pretty shocking to me at the time. I know, it sounds crazy, all these years later. But it was pretty shocking to me, because the brand of humor I use, irony is an important tool in my tool set. And I thought that a lot of kids wouldn’t really understand this character was an unreliable narrator.

And I thought it was a little bit of a mismatch. But of course, I was published, so I went along with it. I really didn’t have to change anything I wrote. I just had to trust that the audience will be sophisticated enough to understand the humor. 

SunLit: Obviously, it turned out that they are. Were you surprised by that?

Kinney: I was. I think sometimes kids pick up my book, and if you’re 7 years old, I’m not sure if he understands. There might be some things that sort of surprise you. But once he gets to be about 8 or 9 years old, I think you can kind of catch all the jokes that are coming your way.

SunLit: Did you think this book would be a one-off, or did you know that you had a series on your hands?

Kinney: Yeah, I really did think of it as a one-off. I thought I’d write one big book. In fact, the first draft was 1,300 pages long. But my publisher told me I should make it into a series to break it up. So at the time I signed a three-book contract, which felt really daring to me at the time, and that got expanded to five and then seven. And now I signed a new three-year contract. And we’ll see where it goes from there.

SunLit: “Rowley Jefferson’s Awesome Friendly Spooky Stories” is your latest book and the one that your tour stops in Colorado are tied to. How does it fit into the overall arc of your work?

Kinney: So Greg (Heffley) has a series called “Diary of a Wimpy Kid.” And Rowley worships Greg, he’s his best friend, but he also looks up to him. And so two years ago, I released a book called “Diary of an Awesome, Friendly Kid,”  which is by Rowley and it’s really a rip-off of Greg’s book. Greg even appears on the cover, sort of complaining that Rowley ripped him off.

And so last year, I came up with the sequel to that, which is called “Rowley Jefferson’s Awesome Friendly Adventure,” which was a fantasy book. So quite different. The “Awesome Friendly Spooky Stories”  is different again. So the Wimpy Kid books are a bit formulaic, they’re based on a template. And the Rowley books are meant to be surprising, each time.

SunLit: The first piece in Rowley’s collection of scary stories is “The Changing,” about a boy who discovers he’s turning into a werewolf — a concept that’s funny and fascinating on multiple levels. Where did you find the inspiration for a “friendly” spooky story like that?

Kinney: It’s funny, I learned a lot. When I set out to write horror stories, I knew I was going to explore different genres like the vampire story, the mummy story and the werewolf story. So I knew I was going to write those types of stories, but I actually learned quite a lot in writing the stories about what the stories were really about. And so I hadn’t really realized until I started writing “The Changing” that the werewolf story is really about puberty. It’s about our unwanted body changes and the power that comes with those changes. So that was kind of fun to explore. And you know, it worked well for the character because Rowley is an innocent kid who really doesn’t want to change. So this change is kind of forced upon him and he has to adapt to it.

SunLit: Tell us a little about your artwork. You mentioned some of your cartoonist heroes. Did they inspire your artistic style?

Kinney: Charles Schultz and Bill Watterson really are fine artists. And I could see that I can never approximate their level of artistry. And so I had to go a different way. I had to come up with a simpler style myself that matched the age of my protagonist. So even the “Diary of a Wimpy Kid” style isn’t my normal cartooning style. It’s just the style that I used to create a realistic drawing style for a middle-school kid. And then Rowley Jefferson’s style is even more down-spec, because Rowley is a more simple-minded, more pure kid.

SunLit: At a time when public appearances by any kind of entertainers are few and far between, you’re taking your show on the road in support of the spooky stories book. Tell me about how and why that decision was made, and what that’s going to look like when it comes to Colorado. 

Kinney:  This has really evolved. Actually, this is the third time I’m getting out on the road during the pandemic. The first time was last August. And I knew that by then, that kids were really sick of Zoom calls, they were sick of looking at adult heads on the other side of the screen. And so I want to do something physical, no matter what it was, or no matter how basic it was. 

So I got out on the road, and I got a van and one of those 9-foot grabber poles, and made it look like a trident. I handed kids books at the end of this poll. And it was really interesting interaction, it was overwhelmingly positive. I think parents were just so grateful to have something to do, and kids were happy to have something that wasn’t cancelled. So that evolved into something much more ambitious, which was the Wimpy Kid drive-thru pool party, which was basically a drive-thru experience where there were lifeguards and giant beach balls and party music.

You drove your car through a tunnel that sounded like you were underwater. And then at the end, I was there dressed up as a lifeguard with a long pool skimmer, and standing on a diving board, so I had books to give kids through their windows. And this time we’re doing a spooky thing. It’s almost like a drive-thru haunted house or a drive through the woods, if you will. And at the end, I’ll be able to hand out books at the end of a shovel, because I’m going to be dressed up as a gravedigger.

SunLit: So this seems like a pretty big production. I’m trying to picture what that will look like to have something that’s large enough for people to actually drive through.

Kinney: I think it’s about 120 feet long. And the experience — it’s not a Disney ride, but it’s pretty cool. We’ve hired a theater set designer, somebody who would usually design for the stage. And so we have these sets that make you feel like you’re in the woods, or make you feel like you’re in a tunnel, or a bat cave. We have an area where you drive your car under a bunch of giant spiders, and through big trees. And then there’s an area where zombies have gotten out of a secret lab. And the zombies, these backlit cutouts, surround your car. So we had a budget that we have to stick with, but we’re trying to make as big of an experience as possible.

SunLit: Have you road tested this one yet?

Kinney: No, we’re gonna hit the ground running. The stores are fabricating everything in a mad rush. They’ll pack it on a truck, drive out to Denver and we’re gonna arrive at the same time and hope that it all works out.

SunLit: Your books are aimed roughly at 8 to 12 years, although certainly the interest goes beyond those numbers. Did you target your audience?

Kinney: Sometimes when I’m writing or thinking, “I don’t think this joke’s great, but maybe a kid would like it” — that’s when I know that I’m on the wrong track. Because I think the reason that the books are working is because they’re not targeting kids. They’re not written to teach kids lessons. It’s humor for humor’s sake, and for entertainment’s sake. So I think that kids expect not to be talked down to, which is important to remember.

SunLit: What do you think makes a good kids book? What advice would you give to parents as they’re looking for good things for the kids to read?

Kinney: I think that humor is always a good thing. Of course, imaginative storytelling is always a good thing. But I find it kind of important not to talk down to kids as a writer, because I think that sometimes, people who write children’s books start off with a lesson in mind. That as an adult, they’re going to impart some wisdom on to the kids. I think there’s plenty of room for books like that. There’s a lot of important books like that. But in my field, which is humor, I think it’s important to just treat kids as sophisticated readers, and to make sure that they’re entertained, first and foremost.

Kevin Simpson is a co-founder of The Colorado Sun and a general assignment writer and editor. He also oversees the Sun’s literary feature, SunLit, and the site’s cartoonists. A St. Louis native and graduate of the University of Missouri’s...