When a wealthy newspaper proprietor passes away, his crooked business partner moves to secure the deceased's fortune by substituting a false will. But 'Corona' Flanagan is onto the fraudster, and his efforts to unmask the villain see him popping in and out of jail – which isn't all that bad, since the governor is an old friend of his – and dressing up as a Russian countess...

Naïve young Englishman, Silas P. Binns inherits a substantial business in Chicago. Unaware of the city's reputation for rampant organized crime during the Prohibition era, Silas arrives in America with idealistic expectations. Upon his arrival, he finds himself inadvertently caught in the middle of a fierce and dangerous turf war between rival gangster factions. The humor of the film stems from Silas's "innocent" and oblivious nature as he navigates the violent underworld of Chicago, often mistaking life-threatening situations for ordinary business or social interactions.

When their ship arrives in an Arabian port, the sailors are given shore leave among them Bill Biggles, who has previously had little success with women. Visiting a sheik who has long been under obligation to him, Bill is welcomed at the palace, and the polygamous ruler, who has abducted a damsel, decides to absent himself and appoint Bill as his deputy. It seems Bill's luck is set to change dramatically until the wives decide to go on strike!

When a pretty Wren faints in a crowded train, Private Bud Flanagan and Captain Ches Allen are quick to render first aid. But over Bud's head, a heavy kitbag wobbles; it falls and scores a direct hit, knocking him unconscious. What follows is a dream sequence involving Ches, the Wren and Bud himself in a series of hilarious adventures as well as a magical medley of the duo's best-loved musical numbers!