Virgil Starkwell's tale cleverly parodies the style of prison documentaries, integrating faux "archival footage" and "interviews" with individuals acquainted with him. His parents, overwhelmed by shame, don Groucho glasses during their interviews to conceal their identities. As a child, Virgil becomes a frequent target for bullies, who joyfully snatch his glasses and torment him. Within the school setting, despite excelling on an IQ test, a notable incident occurs when he pilfers a fountain pen. The teacher, aiming to guide him towards honesty, prompts the class to shut their eyes for the thief to return it. Taking advantage of this moment, Virgil not only returns the pen but also seizes the chance to “feel” all the girls.
Transitioning into adulthood, Virgil exhibits a clumsy and socially awkward demeanor. In a misguided attempt to rob an armored truck, he inadvertently brings a cigarette lighter instead of a gun during a standoff, leading to his arrest. His subsequent prison escape plans falter when he tries to use a soap bar shaped like a gun, only to find the rain dissolving his feeble weapon.
After securing parole, his aspiration to rob a local pet shop crumbles when a gorilla frightens him away. While in the park, he stumbles upon Louise; Virgil reflects on how in just fifteen minutes, he recognized he had fallen in love and wanted to marry her, but after thirty minutes, he dismisses the idea of stealing her purse. He resorts to petty theft, snatching coins from a gumball machine to cover their dinner expenses with nickels, a humorous nod to Cool Hand Luke.
Virgil’s next bank heist falls apart when a disagreement arises concerning his illegible handwriting on a demand note. The cashier becomes bemused by his phrasing, questioning what “I am pointing a ‘gub’ at you” even means, while his assertion that it’s meant to be “gun” is met with skepticism. Amidst the confusion, the police make their entrance, leading to Virgil receiving a ten-year sentence in maximum-security prison. He whimsically requests that Louise bake him a cake, slyly asking for a gun nestled within it alongside a dozen chocolate cookies, each embedded with a bullet—an idea she ultimately doesn’t follow through on.
While in prison, he becomes entangled in a mass escape plan, yet the scheme is soon derailed when guards become suspicious of the vanishing uniforms in the laundry. Unbeknownst to him, he’s left out of the loop but manages to slip away during the chaos.
Upon marrying Louise, Virgil grapples with the challenges of providing for his new family. Misleading potential employers about his checkered past, he finds work in a mailroom. Unfortunately, he falls victim to blackmail at the hands of a colleague, Miss Blair, who coerces him into an unwanted romantic entanglement. In a darkly comedic twist, he plots her demise, disguising sticks of dynamite as festive candles. His assassination attempt ends in farce when he accidentally stabs her with a turkey leg instead, culminating in an explosion from the misused "candles."
Virgil’s streak of misadventures continues with another failed bank heist, thwarted when a rival gang enters the scene, and customers amusingly opt for the other gang to take control instead. This leads to Virgil receiving another ten-year sentence on a chain gang, where he endures harsh treatment alongside an insurance salesman. Echoing the themes of I Am a Fugitive from a Chain Gang, a comical mishap occurs when he asks a fellow inmate if he can smash his chain with a sledgehammer. Unfortunately, the aim is off, resulting in Virgil getting his foot injured instead.
In a nod to The Defiant Ones, Virgil and five other prisoners attempt a collective escape while chained together. Their plans go awry as they hold an elderly woman hostage, orchestrating a ruse for her to claim they are her cousins, all while awkwardly attempting to conceal their chains through synchronized movements. After a scuffle with an officer, they manage to flee, seeking refuge with Louise.
Ultimately, Virgil's journey lands him back in authorities' grasp, as he’s recaptured in an ill-fated robbery attempt against a former friend-turned-policeman. Faced with 52 robbery charges, he receives an astounding sentence of 800 years yet maintains an optimistic outlook, reasoning, “with good behavior, I can get that cut in half.” In a final humorous twist, the film concludes with Virgil diligently carving a bar of soap while inquiring about the possibility of rain outside, leaving viewers with a mix of laughter and absurdity.
