The Drowsy Chaperone is a meta-musical that satirizes the tropes of 1920s book musicals through the lens of a lonely, elderly fan known simply as "The Listener." Living in his apartment surrounded by cast recordings of classic Broadway shows, The Listener decides to listen to the fictional 1928 musical Man of the Month for the first time, with himself donning the role of the Chaperone to narrate and guide the action. As the record plays, the show-within-a-show unfolds in a vibrant, stylized 1920s setting, featuring a chorus of glamorous women, a bumbling detective named Pepe, and a romantic triangle involving the naive maiden Janet Van de Groot and her wealthy fiancé. The narrative blends the fictional story with The Listener’s real-life commentary, highlighting his emotional connection to the characters and his nostalgia for the era’s theatrical optimism. The musical concludes with the resolution of the fictional plot, as Janet realizes her true love is with Pepe rather than her fiancé, while The Listener finds comfort and closure in the power of music to bring joy and meaning to his solitary life.