Anchor plot: During the Great Depression, a rich businessman named Brinkmann decides sink his ship, Anna Susanna, so he would be compensated by the insurance. He orders its captain, Kleiers, to sabotage it while at sea. When Kleiers carries out his instructions, several sailors and passengers notice him. In a fight that ensues, the captain is killed, but not before he manage to shipwreck Anna Susanna. Only a handful of people survive the incident. After they return home, they discover that Brinkmann's insurance fraud worked and he was compensated. They sue him at court and manage to have him indicted.

Plot A: 1940 The Great Depression is over and World War II had just begun. King of the con men Fargo Gondorff is released from prison and reassembles his cronies for another con, out to avenge the murder of his lifelong pal and fellow con artist Kid Colors who was kidnapped, beaten, and then shot.
Gondorff's young protege Jake Hooker attempts to pull a scam on wealthy "Countess Veronique," who instead pulls one on him and turns out to be a grifter herself named Veronica.
Coming up with a boxing con, Gondorff's goal is to sting both Lonnegan, the notorious banker and gangster who wants revenge from a previous con, and Gus Macalinski, a wealthy local racketeer. One or both of them is behind Kid Colors' death.
Hooker pretends to be a boxer who is about to throw a big fight. Macalinski is not only hoodwinked into losing hundreds of thousands of dollars, but he is also talked into changing his original wager by Lonnegan. While one gangster takes care of the other, Gondorff and Hooker head for the train station with a bag full of money, tickets out of town and a final twist from Veronica.

Plot B: In what is being billed as "The Race of the Ages," the new forty-million-dollar “radio powered” Streamlined Ocean Liner S.S. Gigantic (“America’s Challenge for Crossing Record”) is about to race its rival, the slightly smaller S.S. Colossal across the Atlantic from New York’s Pier 97 to Cherbourg in two-and-a-half days. Gigantic owner T. Frothingill “T.F.” Bellows (W. C. Fields) intends to send his nearly identical younger brother S.B. (also Fields) to sail aboard the Colossal, hoping he will cause trouble and sabotage the rival ship, enabling the Gigantic and his own Bellows Line to win.
However S.B., who is held back due to a golf game, ends up flying over the ocean to meet the Colossal en route and mistakenly lands aboard the deck of the Gigantic instead, much to the consternation of Captain Stafford (Russell Hicks). Matters are made worse for the Gigantic when S.B.’s outrageously unlucky daughter Martha (Martha Raye) is brought onboard, being rescued after surviving the shipwreck of the yacht, Hesperus V.
Popular OBC radio emcee Buzz Fielding (Bob Hope), who has just been released from “alimony jail” and is broadcasting live from the Gigantic, is trying to juggle his three ex-wives Cleo (Shirley Ross), Grace (Grace Bradley), and Joan (Lorna Gray); his lukewarm girlfriend Dorothy Wyndham (Dorothy Lamour); and his inept microphone assistant Mike (Ben Blue). Buzz does his best throughout the voyage to announce the progress of the race and introduce a series of musical acts for the pleasure of the passengers and OBC’s radio audience.
Meanwhile, Dorothy is romanced by First Officer (and inventor of the Gigantic’s enormous radio power plant) Robert Hayes (Leif Erickson), just as Buzz and Cleo get sentimental about their broken marriage.