The Drowsy Chaperone was first envisioned in 1997, when McKellar, Lambert, Morrison and several friends created a spoof of old musicals for the stag party of Bob Martin and Janet van de Graaf. In its first incarnation, there was no Man in Chair, the musical styles ranged from the 1920s to the 1940s, and the jokes were more risqué. When the show was reshaped for the Toronto Fringe Festival, Martin became a co-writer, creating Man in Chair to serve as a narrator/commentator for the piece.

Following the Fringe staging, Toronto commercial theatre producer David Mirvish financed an expanded production at Toronto’s 160-seat, independent Theatre Passe Muraille in 1999. Box office success and favorable notices led Mirvish in 2001 to finance further development and produce a full-scale version at Toronto’s 1000-seat Winter Garden Theatre. During that production, Linda Intaschi, Associate Producer of Mirvish Productions, invited New York producer Roy Miller to see the musical. Miller saw potential in the show and he optioned the rights.

With Canadian actor and fund-raiser Paul Mack, Miller produced a reading for the New York’s National Alliance for Musical Theatre on 5 October 2004 – and invited Broadway producer Kevin McCollum. The reading captured McCollum’s interest and eventually resulted in Miller, McCollum and Bob Boyett, Stephanie McClelland, Barbara Freitag and Jill Furman committing to producing the play. An out-of-town engagement followed at the Ahmanson Theatre in Los Angeles (2005), and after alterations, The Drowsy Chaperone opened on Broadway on 1 May 2006.

The concept that the audience is listening to the musical on an old LP record is used throughout the show. As he listens to the show, Man in Chair is torn between his desire to absorb every moment of the show as it unfolds and his need to insert his personal footnotes and his extensive-but-trivial knowledge of musical performances and actors, as he frequently brings the audience in and out of the fantasy. As the show goes on, more of his personal life is revealed through his musings about the show, until, as the record ends, he is left again alone in his apartment – but still with his record of a long-beloved show to turn to whenever he’s blue.

At one point, the record “skips”, which causes the last notes (and dance steps) of a song to be repeated until the Man in Chair can bump the turntable. A “power outage” near the end causes the stage to go dark in the middle of the big production number. Despite the show-within-the-show being a two-act musical, The Drowsy Chaperone is played without an intermission; at the end of the “show”‘s first act, the Man in Chair observes that there would be an intermission “if we were sitting in the Morosco Theatre, watching The Drowsy Chaperone. Which we’re not.” (In the original Broadway production, he added, “They tore it down and put up a hotel,” an in-joke reference to the fact that the show was playing in the Marquis Theatre, part of the Marriott Marquis complex built on the spot where the Morosco stood). His monologue at the musical’s intermission point ends when he changes records (ostensibly preparing the turntable to play the musical’s second act), then leaves the stage “to use the bathroom”. The new record is actually the second act of a different musical by the same composer and librettist, starring many of the same actors. Message from a Nightingale is performed in costumes evoking Imperial China, with the performers displaying cliched Chinese accents and mannerisms. The Man in Chair returns to the stage and replaces the disc with the correct one for Act II of The Drowsy Chaperone.