On paper, it seems like an odd mix of ingredients: The Academy Award-winning screenwriter of the Best Picture winner, adapting an episodic illustrated novel for young readers, about an 11-year-old whose primary companion (and business partner) is a polar bear. But for Tom McCarthy, his feature follow-up to the Oscar-winning Spotlight—Timmy Failure: Mistakes Were Made—was inspired by his affection for the title character.
“I liked [Timmy’s] approach to the world,” McCarthy says. “Every idea for me has to start with one seed, one morsel, one bit of inspiration, and that was a pretty solid bit of inspiration. Beyond that, I didn’t know how I was going to do it.”
That central character, Timmy Failure (Winslow Fegley), is a 5th-grader living with his single mother (Ophelia Lovibond) in Portland, attempting to run a detective agency with that aforementioned polar bear, Total. The raucous book series by cartoonist Stephan Pastis—creator of the syndicated strip Pearls Before Swine—is full of wild misadventures involving its dead serious but often misguided protagonist. But it was a challenge taking that character and crafting a story around him that would work as a movie.

“It took me a while with this one. I couldn’t see the movie for a long time,” McCarthy says. “It’s a challenging adaptation—the many chapters, the sort of organized randomness of it, and how to mold that into a three-act-ish plot, was tricky.”
Pastis himself acknowledges that he was surprised someone would look at Timmy Failure and see the makings of a live-action feature—even though he used the idea of screenplay structure as his foundation when writing his first full-length book. “I didn’t know how to write novels,” Pastis says. “I had read those screenplay books, so I stole that structure. I didn’t do that to write a movie; I did that because I didn’t know how to write a novel. I’m just a cartoonist. I didn’t think anyone would ever turn anything I did into a film, much less Tom.”
Eventually, McCarthy and Pastis shaped the narrative around the connection between Timmy and his mother. “Steph and I early on realized there’s something at the heart of this relationship,” McCarthy says. “It wasn’t just Timmy’s journey; it was their journey, and how they were going to move forward together as a team.”
Once that basic structure was set, there were still plenty of details to fill in. While the book doesn’t set the story in any specific location, McCarthy considered a variety of cities with the kind of peculiar vibe he was looking for—including New Orleans and Minneapolis—before settling on Portland. “The more we dug into Portland, it really just felt like the right community,” he says, “in terms of its spirit, its originality, strangeness, absurdity, all wrapped into one second-city. … I dispatched Stephan up there, and he was sending me the craziest emails: ‘Spent today with a steelworker. Traveled by canoe up to his cabin. Spent the night. Stories to tell will call later.’”

McCarthy also had a unique vision in mind for the mother character—one with a bit more of a funky, hip sensibility than most movie moms, and who doesn’t have a prominent role in the book—that led to some potential awkwardness in the research process. “There were times when I was taking creepy photos of unsuspecting moms in Portland, sending them to my artistic team, until one of my costume designers said, ‘I wouldn’t do this anymore,’” McCarthy says. “I was like, ‘Why?’ ‘Zoom in on the picture, look at the woman’s face. She looks horrified.’”
And then there was the challenge of casting the perfect Timmy. McCarthy and his team landed on Fegley—brother of actor Oakes Fegley, who starred in the recent Pete’s Dragon remake, among other films—who stood out from those who auditioned. “He was the one in 10,000,” Pastis says. “Tom looked at so many kids. At the end, he said, ‘There’s like 15 auditions I want you to look at.’ So I looked at them and I go, ‘That kid? Number whatever?’ And he goes, ‘Yeah.’ He popped out that much. It was crazy.”
With the whole creative team in place, it would be easy to continue making more Timmy Failure adventures, as there are already several more published books. But for McCarthy, it was important to think not about starting a franchise, but about creating one complete and authentic story.

“I think the idea was, ‘Let’s do one really well, then knock it off and walk away,’” McCarthy says. “But, there are other books. Steph’s already playing with a second draft of something, and in reading it, it’s really great to go back and see these characters. Because now we know them so well. That’s why you have a sequel, right? Because you want to spend more time with these characters. If you want to spend more time with these characters, that’s a good reason to make another movie.”
“Timmy Failure: Mistakes Were Made” premieres Friday, February 7 on Disney+.
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