In the bustling city of Portland, Oregon, we meet Timmy Failure, portrayed by Winslow Fegley, an eleven-year-old boy with a flair for entrepreneurship. Timmy thrives in a unique world where imaginary friends coexist with humans, steering his own detective agency known as Total Failure Inc, alongside his trusty polar bear companion, Total. Total serves not only as a sidekick but also as a bittersweet reminder of Timmy's missing father. Together, they embark on a series of adventures across the city, tackling peculiar mysteries and outsmarting a group of bearded hipsters he calls the "Russians," who unwittingly become the source of his greatest hurdles.
Amidst his eclectic group of friends, Timmy leans on Molly Moskins, portrayed by Chloe Coleman, a cheerful girl who secretly harbors feelings for him, and Rollo Tookus, bravely voiced by Kei, who left the agency after a previous mission ended in disaster. Their bonds are tested when Corrina Corrina emerges as Timmy's rival, her genial surface hiding deeper complexities hinted at throughout their interactions.
The story takes a turn when the beloved Failure-Mobile, a customized Segway handed down from his mother, is stolen just as Timmy is attempting to retrieve a deceased hamster. The theft compels him to forgo his other cases and enlist Rollo's help to uncover the mystery. Their investigation leads them to the library, where they stumble upon a trail of clues that imply Corrina Corrina may be behind the theft, seemingly intent on dismantling Timmy's agency.
In his quest for clarity, Timmy seeks the advice of Mr. Jenkins, impressively depicted by Craig Robinson, his school counselor, gradually revealing the nuances of his detective life. Meanwhile, the budding romance between Patty Failure, played by Ophelia Lovibond, and Crispin stirs unease within Timmy, not only due to his animosity towards the aloof Crispin but also regarding Patty's reluctance to cooperate with law enforcement. This flurry of emotions adds layers to Timmy's resolve to solve the case.
As Timmy digs deeper into the enigma surrounding Corrina, he learns of her father's powerful influence in the community, prompting him and Rollo to hatch a scheme to infiltrate the bank. However, their endeavor is swiftly thwarted when security catches them in the act. During this tumultuous time, Mr. Jenkins cleverly turns Timmy's homework into a "mission," while the revelations of Patty’s own family struggles hit home for Timmy—especially their impending move to a new apartment.
As the class embarks on a field trip to Bonneville Dam, Timmy's imagination runs wild, leading him to mistakenly believe that Corrina plans to halt the city's power supply. Fueled by urgency, he races against time, eluding his teacher, Mr. Crocus, with a determination born from misunderstanding. The chase culminates in a moment of mistaken heroism, as Timmy tries to shield Mr. Crocus from a flood that never truly threatens them.
The aftermath sees Timmy facing a three-day suspension, while Mr. Crocus's absence leaves a gaping hole in his academic life. Pattys frustration boils over with her own job being cut, leading her to stay home and manage what remains of Total Failure Inc, which ultimately withers away. These cumulative challenges force Timmy to confront the reality of leaving behind his unorthodox adventures and grasping for a more "normal" life.
As poignant wisdom flows from Mr. Jenkins about learning from one's failures, Timmy’s spirit reignites when he discovers a hidden "Russian bug" in his cookie. This spurs him into action, teaming up with Crispin on a daring journey to rescue Total from the confines of the local zoo. Their misadventure takes a thrilling turn when they encounter a purse snatcher, leading Crispin to spring into action before Timmy opts to let the professionals handle it, calling 911 with newfound maturity.
With further escapades unraveling, including a mishap involving his truck and a chance encounter with a passerby, Timmy begins to find his bearings. In a surprising turn, Crispin reveals the Segway's location at the police station, igniting Timmy’s conspiracy theory about collusion with the Russians. As he gears up to speak at an animal fundraiser hosted by Molly, he captures the audience with his fervent topic about polar bears in schools.
As night falls, Timmy's heartfelt desire for Mr. Crocus to witness his triumph leads to an unexpected epiphany: the terrifying thought that Corrina Corrina may have taken Mr. Crocus captive sends him on a heartfelt mission to rescue his friend, with Total by his side, determined to uncover the truth behind the chaos in his life.
