Virgil Starkwell, an inept criminal with grand ambitions, struggles to achieve success in the world of crime. From an early age, his attempts at delinquency are thwarted by his lack of skill and sheer bad luck. Despite numerous failed heists, arrests, and botched schemes, Virgil remains determined to make a name for himself. Along the way, he encounters Louise, a kind-hearted woman who eventually becomes his girlfriend. Louise's love offers Virgil a sense of stability and purpose, even as he continues his misadventures in crime.

Virgil's journey is marked by a series of comical escapades, including disastrous bank robberies and humorous encounters with law enforcement. His bungling efforts lead to various prison sentences and numerous attempts to break free from jail, each more outlandish than the last. Throughout his chaotic life as a crook, Virgil's earnest yet misguided determination serves as a constant source of humor and sympathy. As his story unfolds, viewers are taken on a rollercoaster ride of laugh-out-loud moments that portray the trials and tribulations of a man who just can't seem to catch a break in the underworld of crime.