Double or Nothing: Double or Nothing: A rich man's will gives a singer (Bing Crosby) and three others 30 days each to double $5,000 honestly and win $1 million.
East side of Heaven: A singing cabby (Bing Crosby), his fiancee (Joan Blondell) and his roommate (Mischa Auer) tend an abandoned baby sought by the police.
Here Come the Waves: Complications abound when a singing sailor falls in love with a service-woman whose identical twin can't stand him. Will the interfering sister dash any hope of true love?
If I had My Way: Two friends (Bing Crosby, El Brendel) of an orphan's (Gloria Jean) father take her to New York to find her guardian.
Waikiki Wedding: Advertising agent Tony Marvin (Bing Crosby) devises a campaign for Todhunter's Imperial Pineapples in Hawaii to select a "Pineapple Girl" to find romance in Hawaii for three weeks, and later relate her adventures in print. When Georgia Smith (Shirley Ross) is selected but fails to find romance, Tony is pressured into providing it. Unknown to him, Todhunter also arranges for Tony and Georgia to receive a mysterious black pearl, which will lead them to an adventure on a smaller island.