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Timmy Failure: Zero to Hero Interview with Stephan Pastis

Be like Timmy.

Before Timmy Failure dies, he wants to achieve greatness. If he does achieve it, and then loses it, he wants to reclaim greatness. Be like Timmy.

Timmy Failure is an 11-year-old boy and the world’s greatest detective… at least, he likes to think so. Timmy’s detective agency, Total Failure, Inc., is run by Timmy himself and his polar-bear partner, Total. From vanishing candy and missing library books to the Great Shirt Heist, Total Failure, Inc. is the clueless yet confident detective agency one needs (at least for comic relief).

Author and cartoonist Stephan Pastis is the mastermind behind the New York Times best-selling Timmy Failure series. He is also the creator of acclaimed comic strip Pearls Before Swine which appears in more than 700 newspapers.

We were lucky enough to check out the long-awaited prequel to the Timmy series, Zero to Hero, set for release on April 7. In it we learn how Timmy became the best detective in Portland, Oregon; the story behind that famous red scarf of his; as well as discovering Total’s knack for negotiation in becoming an agency partner. It is an unconventional and ridiculously lovable story about growing up. 

We should also mention that we are still recovering from the belly laughs we endured after watching Timmy Failure: Mistakes Were Made on Disney+. No ab workout required the day we watched that film – it was all in the laughs. 

I don’t have kids but I imagine Timmy Failure embodies the sort of confidence, quirk and self-assurance you may want your own kids to have (though his appetite for risk-taking could certainly be taken down a few notches). I had far too much fun chatting to Stephan about his thoughts on Timmy and where all that creative genius comes from.

You don’t need to worry about Timmy Failure being the odd kid out. He is, and he relishes in it. That’s what makes Timmy, Timmy. Right, Stephan? How do you describe Timmy?

Right. Timmy is a kid who copes with the world by relying on his imagination. It is sort of like his protective device to deal with a world he doesn’t fully understand and isn’t quite able to cope with.

Tell us when, where and how the idea for Timmy Failure came about. What inspired you to write the series?

A book agent who was a fan of the comic strip [Pearls Before Swine] called and asked if I’d be interested in writing a book. At the time, I said I didn’t have time, but he ended up calling a few times and finally I said I’d try it. When he asked me what I want to write, I started thinking about what was appealing to me: characters that have big blind spots, how the world views them versus how they view themselves. The wider that gap for me, the funnier the character. 

A detective is suited for that because detectives are supposed to be really on top of things and, and that’s how to Timmy sees himself, but that’s obviously not how he is. I then just started writing with no outline or anything which is how I’ve done most of the books. 

How did Pearls Before Swine influence the Timmy Failure series, if at all?

Even though comics aren’t the same as they used to be with newspapers suffering as they are, I still put out a comic strip every day and have done so for almost 20 years. Comic strips provide amazing training on interacting with an audience. I get a reaction every day. That allows you to know what will play and what won’t, topics to avoid, topics that anchor people, etc. 

When I wrote Timmy Failure as a script for the movie, it was all about brevity – just like a comic strip. In that way I was working a muscle I didn’t even know I had. Writing the books was just a joy because they allowed me to take a joke and span it across 300 pages. In Pearls Before Swine I can’t do that because you’re so limited for space which is the single most defining feature of a comic strip. So, when someone said, “here’s 300 blank pages – go!” I loved it. 

That must be challenging to go from a speedily arriving punchline in comics to a novel-length joke or series of jokes. How do you keep readers laughing for that many pages?

That was hard. The thing with the comic strip is that I can hold it at arm’s length and see it in its entirety. But with a book I can’t, so when I first started writing the Timmy books (this is so crazy and any writer worth their salt would just laugh at this) every day before I wrote, I would read the entire book up to that point. I did this so I could remember where everybody was and what they were doing, what Rollo did last, etc. That was the equivalent of holding the comic strip out at arm’s length. So, the length posed that challenge because, in some ways, some of those jokes are the length of the book and in order for the rhythm to work, I have to be able to see it all. I’m sure there’s easier ways to do it, but that is how I did it. 

What was great about doing the books and the movie was that I felt like “you don’t know what you don’t know.” That totally protects you and makes you fearless; ready to jump into it. I like jumping into something new and trying to figure it out. It’s exciting to me.

There are many significant lessons the Timmy series teaches us, including embracing the “wild cards, misfits and dabblers”; fighting for what you love; and adapting if something is not going your way. What themes or lessons were particularly important to you as you wrote these books such that you felt compelled to include them?

I guess it was about any kid who was missing a parent – they’ve either died or they’re divorced, whatever the case may be – and that they can be themselves and feel okay. They can feel whole and sort of be celebrated for it. I have always seen Timmy as a hero, despite his goofiness. I would tell the director of the film this all the time. Despite all of his limitations (and he has a lot of them), he always thinks he’s going to succeed. The reason that makes him a hero in my book is because if a kid is looking at Timmy and Timmy thinks he can succeed despite all of his limitations, then that kid reading the book can succeed. 

We love Timmy and Rollo’s relationship in Zero to Hero. Rollo straddles his school responsibilities with his whimsical life (like most of us). Did you always have a nervous, hardworking elementary school pal (and on-again, off-again Total Failure, Inc. employee) in mind from the beginning or did Timmy and Rollo’s relationship evolve from the plot?

Rollo was based on my friendship with my one and only friend in life. We’ve been friends since kindergarten. His name is Emilio and I brought him to the movie set and I introduced him to Kei (plays Rollo in the film) and told Kei, “this is the real-life version of Rollo!” Emilio and I were best friends and our relationship is much like Timmy and Rollo’s relationship (except I was the one who did better in school!). 

Emilio must feel famous now!

(Laughs) Yeah, I brought him along to the Hollywood premiere in the Disney limo. It was cool.

You use many different formats and writing styles in Zero to Hero: novel writing, transcript writing, letter writing, and even footnotes. We thought it was a fun, unusual way of keeping your reader engaged. Why did you choose to include different styles in Zero to Hero?

I wish I would have let Rollo footnote even earlier than in Zero because it was so much fun. Timmy is your unreliable narrator and Rollo provides another voice. It was great because you could see Timmy’s lies in real time. Having done seven of these books before, I needed to keep myself interested in it and be excited by it. I had never previously played with the format that much before so that was really intriguing to me.

I was influenced by Kurt Vonnegut (Slaughterhouse Five, Breakfast of Champions) and I really love folks who break the fourth wall. In Pearls, I have made myself a character, I make fun of other strips, etc. I am constantly trying to do something that I will find interesting because, if I have learned anything in all of these years, if I bore me, I will definitely bore you.

Did your kids help you write or otherwise inspire you in any way for this series?

I always had both my kids, Tom and Julia, read the books first and – even more annoying for them – I sat with them as they read it. When they laughed, I asked: “okay, what was funny?” And when they didn’t laugh, I’d be like, “Oh, you didn’t think that was funny?!” (Laughs). I did that with them on every book and they hated it and it really helped. If both my kids laughed at something, I fought for it more during the editing process if the editor later tried to cut it. That was like my barometer. It was a really big help.

Tell us a bit more about your writing process.

I play music at an exceptionally loud volume. I light incense and turn off all the lights and then I type as fast as I can. And what happens, happens. That’s how every single part of Timmy came about. I am the opposite of a writer who plans meticulously. I think that would bore me. I’m much more curious to see what will happen in the course of the process. 

There is no part of this book that was thought out. The crazy part about writing the way I just described is how much you reveal of yourself whether you intend to or not. And it is not until later that you understand why you might have included something. For example, after spending a whole day writing I’ll suddenly stop and think, “Oh, the aunt in the book is just like my grandmother.” I never once while writing consciously thought, “I am going to do a character based on my grandmother.” I don’t know why more people don’t write that way. There is so much better stuff in your subconscious.

Why do you think you created Total as a polar bear, as opposed to a human, object, or some other animal or creature?

I think I wanted to give Timmy a friend who would act kind of like a stand-in for the father he doesn’t have. I thought it was an odd pairing too because Timmy is small and the bear is so big. Total is also soft and a protector. Having a protector is comforting. I never thought of that going into it but I now see that that’s probably what was going on. At least, that is my guess as to why it was a polar bear as opposed to an anteater or something.

Do you have a favorite Timmy book?

Oh, that is like picking your favorite kid. I love all of my books equally. 

Who is your favorite character in the Timmy series and why?

Timmy for sure. He is my natural voice. I share so much with him. 

What have been your favorite parts of writing the Timmy books and why?

Every time I do it, it is almost like seeing an old friend that you haven’t seen for a long time. It had been a while between book 7 and book 8, and I remember saying to my wife that I missed Timmy. He’s almost real to me. I don’t feel like I created him, I feel like I see him and it was neat to see him again.

What challenges did you face writing the books and how did you overcome them?

A big challenge, or mistake I’ve made, is writing a whole book and then having to go back and illustrate the entire thing. It is much easier to illustrate every chapter or every few chapters because you forget how long it takes to draw certain things. The writer in you forgets about the drawer.  

Another challenge is as you get deeper into the series, characters already have stories, so you are more and more limited because you have to remember their background. In the first book you just let loose and whatever you say they are, they are. You don’t have to remember it. 

Zero was probably the most challenging because it is Timmy after seven books knowing he is famous and is now telling you his origin story which is about events before the very first book. Prequels are harder because everything you write has to lead into book one. It is sort of like the difference between doing a Rubik’s cube that someone just hands you and doing a Rubik’s cube that has five of the sides already done and you’ve just got to get the sixth side, which sounds simple, but it’s not, because anything you do affects the other sides.

What are the pros and cons of Timmy Failure as a book vs. as a film?

The advantage of the book is that I have total freedom to write anything I want to write with no limitations. I also have to do everything in the books. The tendency of a writer when they get to do a movie is also that they try to do everything. But you don’t have to – you can rely on a lot of other professionals doing their job and it works really well. 

So, the advantage of the movie is that no matter what I write someone executes it in a great new way. The movie has to be grounded, but you also have the power and skill of the actors behind you. 

I was on set every day that we drove a car into a building for a scene in Timmy Failure: Mistakes Were Made. Here was a stunt driver going 40 miles an hour into a house. I couldn’t stop thinking, “man, the only reason this is happening is because I wrote it.” It was such a cool feeling. 

We thought the cast for the film was perfect. Did you have any say in the casting decisions?

Yes! Writers are not typically involved in casting but the director, Tom McCarthy, was so nice. He allowed me on set and got me involved in all the departments from props to wardrobe and even the look of Total. Ultimately all the decisions were Tom’s decisions but he asked for my input and that was super nice of him.  

I read in one of your Pearls Before Swine comics Rat asking Goat a great question that I would now also like to put to you: why do creative people create?

I think because you’re compelled to – you’re pushed forward by something bigger than yourself. It is a way that I can express myself. It is an outlet. I love seeing what’s out there. I write like a person would fish for the discovery. Like, am I going to catch something? If a fisherman goes to a grocery store and buys the fish, you’ve taken all the joy out of it for him. So writing is like fishing for me in that way. It’s that joy of what might be there. Some days there nothing is there. But on the days that something is there, it is so much fun. It’s a rush.

What do you ultimately hope readers get out of the Timmy Failure series?

I want them to laugh. I always feel like that is my first job. I also want them to be inspired to read more books; not just mine, but books in general. If I achieve those two things, I have succeeded.

Timmy Failure: Zero to Hero is available for preorder on Amazon and is set for release on April 7. In the meantime, check out the other books in the series listed below, as well as the original movie on Disney+ ‘Timmy Failure: Mistakes Were Made.’ (Also, keep an eye out for Stephan’s cameo in the film – he is the real estate agent featured on the brochure Timmy reads in bed!)

  1. Timmy Failure: Mistakes Were Made
  2. Timmy Failure: Now Look What You’ve Done
  3. Timmy Failure: We Meet Again
  4. Timmy Failure: Sanitized for Your Protection
  5. Timmy Failure: The Book You’re Not Supposed to Have
  6. Timmy Failure: The Cat Stole My Pants
  7. Timmy Failure: It’s The End When I Say It’s The End
  8. Timmy Failure: Zero to Hero