A Kid Detective and His Pet Polar Bear Keep Portland Weird in the Disney+ film “Timmy Failure”

Thematically the final message is: Keep your uniqueness intact, as long as it’s prosocial.

In a post-Portlandia world, bottling Portland's whimsy for the screen without including either ample irony or blissful ignorance is a challenge. Yet the new Disney+ movie Timmy Failure: Mistakes Were Made takes an interesting middle tack: Stumptown strangeness as seen through the eyes of a child with a hyperactive imagination.

Mulleted kid detective Timmy Failure exaggerates our local color in his pipsqueak noir, and sometimes the joke in the Portland-shot kids' movie is how little he needs to exaggerate. The fifth-grader, played by Winslow Fegley, pegs waxed-mustache hipsters as Russian spies. His CGI polar bear sidekick, Total, swims the Willamette River under the cover of darkness. And the Bonneville Dam serves as the readymade backdrop of a '70s thriller playing out in Timmy's mind.

The new film from Spotlight director Tom McCarthy—it's a departure for him, to be sure—sees Timmy gallivant around North Portland's Overlook neighborhood, cracking cases of his own creation and pushing his poor mother and teachers to their emotional limits. Supporting cast Craig Robinson (The Office, Hot Tub Time Machine), Wallace Shawn (The Princess Bride, My Dinner With Andre) and Ophelia Lovibond (Elementary, Rocketman) take turns corralling Timmy, who communicates like IBM's Watson reading dialogue from a Dashiell Hammett hard-boiled detective novel.

Based on the first in a series of children's books by Pearls Before Swine cartoonist Stephan Pastis, Timmy Failure has scant setting in its written form, so Portland infuses the story with color. This includes the characters. In a scene-stealing turn, former Portland standup comedian Caitlin Weierhauser (one of WW's Funniest Five in 2017) made the story's ominous biker librarian Flo all their own.

Though Weierhauser says Flo reads as a man in the books, they had many conversations with Pastis and McCarthy on the set about comfortably portraying the character as nonbinary, which is how Weierhauser identifies offscreen. It's a seamless fit. Flo commands their desk of the fictional Northeast Portland Library, covered from wrist to neck in tattoos while rocking a leather biker vest that offers the friendly ultimatum "Read or Bleed."

"They knew I wanted to take [that vest], so I got put on watch," Weierhauser jokes. "It was an actual beat-up biker vest. In the pocket, there was still an old security card. So authentic, man."

Though Weierhauser moved to Los Angeles in 2018 and performed on The Late Show With Stephen Colbert last year, they shot this, their first movie role, just months before departing Portland. The experience was overwhelmingly positive. Weierhauser praised the scope and professionalism of the $42 million Disney production and marveled at how McCarthy could manage the film's climactic scene at St. Johns' Cathedral Park through a bullhorn and still slip Weierhauser a constructive note about the tone of a single line.

"If there was a wrong way to do something," Weierhauser says, "I tried it."

That self-deprecation doesn't show in the finished product. Weierhauser cuts a striking, no-nonsense foil to Timmy's sometimes alienating chatter, rendering Flo a larger-than-life authority figure whom children reared on Disney+ today might memeify a decade from now. That said, some of Weierhauser's scripted scolding of rowdy elementary-schoolers might've been too convincing.

"In one scene, I'm yelling at them to shut up and pay attention, and they started to get really quiet on set," Weierhauser says. "From take to take, their rambunctiousness really tapered off. Tom would come back and be like, 'Kids! I need you to be [excited]!' And they'd be like, 'No! This biker keeps yelling at us!'"

While the script does sometimes leverage Timmy's emotional immaturity against Portland's own codes about staying weird, thematically the final message is, of course, inspirational. Keep your uniqueness intact, as long as it's prosocial.

"It was something me and Stephan and Tom had multiple conversations about: [my] utter exhaustion with this weird little twerp who won't stay out of my G.D. library," Weierhauser says of their character, "but Flo does want something better for Timmy. At the base, there's love, and that's what we kept coming back to."

SEE IT: Timmy Failure: Mistakes Were Made streams on Disney+.