Act one begins with The Man in Chair, a mousy, vaguely depressive Broadway fanatic whose coping mechanism involves listening repeatedly to a recording of a 1928 stage show, The Drowsy Chaperone. When he first turns on his phonograph and static breaks from the speakers, he wistfully tells the audience, "I love that sound. To me, that’s the sound of a time machine starting up." By the time the first note sails out of his speakers, he's been transported to a magical dream world, one where the actors in the recording enter his dingy apartment and transform it into a gloriously garish set complete with seashell footlights, sparkly peacocks, glittery sugarplum trees, and costumes that would put the Ice Capades to shame.

The show-within-a-show centers on a vain showgirl, who is about to marry a man she only just met, and her cigar-chomping producer, who doesn’t want to lose his valuable startlet.  What follows is a pastiche of every cliched plot thread ever written, including mistaken identity, spit-takes, and gangsters on the lam, involving such campy characters as an all-knowing English Butler, a Latino Lothario, and a daffy, cartwheeling heroine. Watching from his armchair, Man in Chair is torn between his desire to absorb every moment of the play as it unfolds and to insert his own personal footnotes as he continuously brings the audience in and out of the fantasy.