The show has had major productions in Toronto, Los Angeles, New York, London, Melbourne and Japan, as well as two North American tours as well as Batemans Bay in New South Wales.

The Drowsy Chaperone started in 1997, when Don McKellar, Lisa Lambert, Greg Morrison and several friends created a spoof of old musicals for the stag party of Bob Martin and Janet Van De Graaff.

Box office success and favourable notices led Mirvish in 2001 to finance further development and produce a full-scale version at Toronto's 1000-seat Winter Garden Theatre.

The production featured sets by David Gallo, costumes by Gregg Barnes, lighting by Ken Billington and Brian Monahan, hair by Josh Marquette, and makeup by Justen M.

[4] The original cast featured Bob Martin as Man in Chair, Sutton Foster as Janet, Georgia Engel as Mrs. Tottendale, Edward Hibbert as Underling, and Beth Leavel as the Chaperone.

Upon Engel's exit from the production, Jo Anne Worley and Cindy Williams became replacements for Mrs. Tottendale, Mara Davi assumed the role of Janet once Foster left, and Peter Bartlett took over for Hibbert.

"[5] In a slightly more enthusiastic review, Variety's David Benedict noted that "The secret behind the success of Casey Nicholaw's exquisitely honed hymn to the forgotten musicals of yesteryear is that its authors knew exactly what they were doing when they took the broad out of Broadway.

A largely British cast, including Elaine Paige – making her return to the West End after six years – John Partridge and Summer Strallen joined the show's co-author Bob Martin recreating his Broadway role of "Man in Chair", with Anne Rogers, Nickolas Grace, Nick Holder, Selina Chilton and Adam Stafford.

[9][10] An early drastic reduction in the cost of premium seating for the show failed to generate sufficient enthusiasm for the production, and the producers closed it in August instead of the scheduled February 2008 date.

The Drowsy Chaperone played more than 30 cities in the United States, including Los Angeles at the Ahmanson Theatre, where the show ran before going to Broadway.

The cast of this version included Jay Brazeau, Thom Allison, Debbie Timuss, Laird Mackintosh, Gabrielle Jones, Neil Minor, Shawn Macdonald, Mark Burgess, Nathalie Marable, Nora McLellan and David Marr.

[16] In co-production with Canada's National Arts Centre English Theatre, the Vancouver Playhouse Theatre Company's production of The Drowsy Chaperone directed by Max Reimer played on the Shoctor stage of the Citadel Theatre in Edmonton, Alberta, opening on 5 September and closing on 4 October (2009) and thereafter played at the National Arts Centre though 1 November 2009; however, musical director Lloyd Nicholson died of a heart attack on the eve of the first performance in Ottawa, causing the production's run in that city to be truncated slightly as a couple of early performances were cancelled.

[17] The Drowsy Chaperone ran 30 June – 11 July 2015 at the Cape Playhouse in Dennis, Massachusetts with Jo Anne Worley reprising her Broadway role of Mrs. Tottendale: the cast also included Simon Jones as Man in Chair and Bill Nolte as Feldzieg.

In the cast there were popular Brazilian musical actors such as Ivan Parente, Sara Sarres, Stella Miranda, Saulo Vasconcelos, Kiara Sasso and Andrezza Massei.

[25] Man in Chair, a mousy, agoraphobic Broadway fanatic, seeking to cure his "non-specific sadness", listens to a recording of the fictional 1928 musical comedy, The Drowsy Chaperone.

As he listens to this rare recording, the characters appear in his dingy apartment, and it is transformed into an impressive Broadway set with seashell footlights, sparkling furniture, painted backdrops, and glitzy costumes.

In the opening number, "Fancy Dress", the premise and characters of the show are introduced: it's the day of the wedding of oil tycoon Robert Martin and Broadway star Janet Van De Graaff, who plans to give up her career for married life.

Those in attendance include aging hostess Mrs. Tottendale; her loyal employee known only as Underling; Robert's best man, George; Broadway producer Feldzieg, who is hoping to persuade Janet to forgo marriage and continue starring in Feldzieg's Follies; ditzy flapper Kitty, who hopes to take Janet's place in the Follies; two gangsters disguised as pastry chefs; self-proclaimed famed Latin lover Aldolpho; Janet's alcoholic Chaperone, who is supposed to keep her away from Robert until the wedding; and Trix, an aviatrix.

George notes that tap dancing could be injurious, so he suggests that Robert go roller skating in the garden instead, while wearing a blindfold to keep him from seeing Janet.

Outside by the pool, Janet tells reporters that she is happy to be getting married and ostensibly doesn't want to be an actress anymore ("Show Off"), but her song evolves into a big production number.

[a] Man in Chair puts on another record, saying that the audience can listen to the opening of the second act of The Drowsy Chaperone, and leaves for the restroom.

As the record is about to play the show's final chord, the power goes out in Man in Chair's apartment, and a superintendent arrives to check the circuit breakers.

The original cast recording contains two bonus tracks titled, "I Remember Love," which is a duet between Mrs. Tottendale and Underling, and "Message From A Nightingale", which is the unabridged version of a portion of a song that is cut short in the show.

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 bumps the turntable.

The plot incorporates mistaken identities, dream sequences, spit takes, a deus ex machina, an unflappable English butler, an absent-minded dowager, a Broadway impresario and his Follies production, comic gangsters, a ditzy chorine, a harried best man, and Janet's "Drowsy" (i.e. "tipsy") Chaperone, played in the show-within-a-show by a blowzy Grande Dame of the Stage, specializing in "rousing anthems" and not above upstaging the occasional co-star.