The story concerns a middle-aged, asocial musical theater fan who, feeling "blue", decides to play for the audience an LP (Yes a vynil record) of his favorite musical, the fictional 1928 show The Drowsy Chaperone. As the record plays, the show – a parody of 1920s American musical comedy – comes to life onstage, as the Man wryly comments on the music, story and actors. The fictional musical is about the intrigues surrounding an about-to-be-wed oil Tycoon and a Broadway starlet.