Directed by Tom McCarthy, Timmy Failure: Mistakes Were Made streams on Disney. The story comes from the bestseller of the same title by Stephan Pastis, who co-wrote the screenplay with McCarthy. Timmy Failure is a unique young boy, played by Winslow Fegley, with a polar bear as his assistant. Producer Jim Whitaker had this to say about Fegley, “He’s the one who was able to play Timmy from just the point of view of being himself and, at the same time, not understand there’s a hint of irony in any of the humor that’s played. He plays it straight, uniquely, and as a result of that, brilliantly.”
“Right off the bat, Winslow had a quality and look that felt right,” says director McCarthy. “He just had a really good command of [the] language, and for a young actor, he has a lot of poise and a tremendous amount of presence. And he has a quality that no matter what he’s still somewhat accessible, and Timmy can be the kind of character that pushes people away. Timmy’s a different kid, he doesn’t have a lot of friends, and he’s a tough kid to get close to, so you need someone who can play both sides of that.”
British actress Ophelia Lovibond plays Patty Failure, a single mom struggling to survive economically while raising her son Timmy. “The script is unlike anything else I’d read, and even though it was described as being for children, I genuinely enjoyed it…it really made me laugh,” says Lovibond. “The character of Timmy is so unusual…he just captures your imagination.”
“Patty is a hardworking hipster who’s trying to hold together a household, several jobs, and at the same time be able to allow for this very different kid to be who he is,” adds Whitaker. “Ophelia has done a beautiful job with the role. She’s a Brit undercover who looks and acts like she’s from Portland.”
To get into character, Lovibond dyed her hair purple and wore fake tattoos. “Each tattoo has a story behind it,” she says, “like one hasn’t been colored in because she got it and then Timmy came along, and she had no money to have it finished.”
Timmy’s teacher and nemesis, Mr. Crocus, played by Wallace Shawn. “He plays this curmudgeonly, angry, not-willing-to-smile, absolutely going to persecute this unique kid into submission, until he ultimately discovers that Timmy’s going to get the better of him, and is really funny,” says Whitaker.
Says Shawn, “My character represents society and authority in the movie, but Timmy believes himself to be a detective, not a student in the 5th grade, so he is not afraid of Mr. Crocus’ threats, so Mr. Crocus is, in a way, powerless.”
Craig Robinson plays Mr. Jenkins, a laid-back guidance counselor at Timmy’s school. “Mr. Jenkins really cares about his students,” says Pastis, “sort of the opposite of Crocus. He wants to find out what makes these kids tick and get to them that way. For Timmy, he realizes it’s the detective-agency stuff, so he takes that path.”
“I love that he’s the one that keeps it real with Timmy,” says Robinson. “He’s the one that says, ‘You don’t have to be like everyone else,’ and that’s why I wanted this role. It’s also a departure from what I normally do, but it’s special to be the person who believes in our hero and gets him to the next level.”
Kyle Bornheimer plays Crispin, Patty Failure’s earnest yet misguided boyfriend, and a parking enforcement officer, which Timmy sees as an unambitious career path. “Timmy tends not to be very trustful of new adults in his life,” says Pastis. “He also sees him as an intruder, because Timmy lives alone with his mom, and he doesn’t like someone else coming over to their house.”
Crispin is the one character who changed the most significantly from the book to the screen. “In the book, he’s a pretty bad character through and through,” says Pastis. “But not this, Crispin. This Crispin is rather sweet and endearing.”
For Bornheimer, playing the role of Crispin was a no-brainer. “My kids are big fans of these books, so it was a chance for me to play a role that my kids could see,” he says. “And then the character himself was just this fun, kind of pure-of-heart but a little bit of a bull in a china shop…a character too good to pass up.”
“Crispin ends up getting in Timmy’s heart because he really believes in him,” says Whitaker. “There’s a great scene in the movie where Timmy is forced to ask Crispin to help him find a 1,500-pound polar bear and Crispin just says, ‘Cool, let’s go.'”
Kei plays Timmy’s best friend, Rollo Tookus, but they’re more like frenemies because they don’t get along with each other all that well. “Rollo is a little anxious because he obsesses about his grade point average as he wants to get into Stanford when he gets older,” says Pastis. “A lot of the semester is spent on group tests, and Timmy is in Rollo’s group, so he’s scared to death Timmy will tank his GPA, which he will. So I think they’re friends because for Rollo, Timmy’s kind of exciting…even though he might not admit it.”
Chloe Coleman plays an animal activist classmate of Timmy’s, Molly Moskins. Molly is in love with him, but Timmy barely knows she’s alive. “That’s the relationship. It’s funny because she keeps flirting, and Timmy doesn’t know what that is. He just thinks that’s odd behavior,” says Pastis.
Ai-Chan Carrier is Corrina Corrina, a pleasant and upbeat student who is well-liked at Timmy’s school. Timmy, however, is convinced she is in cahoots with the Russians and plans to destroy his detective agency.
All in all, Timmy is a quirky, deadpan 5th grader from Portland who, along with a 1,500-pound polar bear named Total, operates Total Failure Inc., a detective agency. Somewhat of an outsider at his elementary school, Timmy is clueless but confident and wants to see his detective agency become the best in the world. But first, he must navigate the world of adults around him. As mentioned early, they include his mother Patty, her boyfriend Crispin, his teacher and nemesis Mr. Crocus, and Mr. Jenkins, a school-mandated guidance counselor. Failure journeys with Total and figures out what it means to be “normal” when you know deep down inside you’re different.
