The show revolves around one musical theatre fan’s obsession with a fictional show from the 1920s - ‘The Drowsy Chaperone’. As he listens to the recording, the characters come to life in his apartment. This is the story of a Broadway actress, Janet Van De Graaaff, who wants to marry the debonair Robert Martin and give up her stage career. Janet’s producer, Mr. Feldzie, must stop the wedding because if she quits show business, he'll lose his job! Further, gangsters threaten Mr. Feldzie since if Janet quits, they lose their investment.