The Whoopee Boys

A dim-witted yet good-hearted street peddler who pairs with Barney to climb into high society. He flirts with Olivia and uses bold improvisation to win favor and aid the orphanage. His confidence often masks his insecurities about belonging to the upper crust, and he learns to adapt on the fly as plans unfold.

An heiress who runs an orphanage and is pressured by her uncle to marry a 'Perfect Gentleman.' She tests Jake’s sincerity and gradually falls for him, challenging the social dynamics of her world. Her conflict between duty and love drives much of the plot and the choice she must make.

Jake’s loud, big-hearted partner who hopes for a better life. He joins the charm school with Jake and provides boisterous humor and loyal companionship, helping to pull off their scheme at pivotal moments. His antics keep the plan afloat even as it teeters on the edge of failure.

A renowned etiquette expert who runs the charm school that trains Jake and Barney. Her methods blend polish with sharp social insight, guiding them through the art of appearing cultured. She and her husband orchestrate the social theater that underpins the plot.

Henrietta’s husband, a military man who oversees a secret society within the etiquette world. He uses staged scenarios to teach their students how to act like refined gentlemen. His presence adds a satirical edge to the idea of exclusive circles.

A real estate developer and Olivia’s fiancé chosen by her uncle. He embodies wealth and control, serving as the primary antagonist whose plans hinge on Olivia’s compliance. His position is upended by the wedding-day ruse and the social shifting that follows.

The wedding’s gatekeeper who must approve the union. He represents the authority that polices social norms and class boundaries. He is won over by the duo’s performance and by the end recognizes the sincerity of their intentions.

A sharp police officer who becomes an instrumental part of the wedding-day ruse. Her actions blur the line between law and spectacle, contributing to the film’s chaotic, comedic energy. She embodies the comedic authority that tightens or loosens control at key moments.

A nerdy, eager accomplice whose talkativeness and naiveté provide comic misdirection. He unwittingly confesses to White about the charm-school scheme, which accelerates the story’s complications. His role is pivotal in tipping the plan toward its theatrical climax.